B

Mildred Bailey (1903–1951)

Tony Bennett and Rosemary Clooney first met each other around 1948, when both future stars were still unknowns. When Clooney heard Bennett sing for the first time, she asked him, “You’ve been listening a lot to Mildred Bailey, haven’t you?” Bennett answered in the affirmative, as Bailey was indeed one of his all-time favorites. He then complimented Clooney on her perception: certainly fifty years ago he didn’t sound any more like Mildred Bailey than he does today. Yet the influence was there—and indeed, still is.

What did Clooney hear in Bennett’s singing that she recognized as Bailey’s influence? Bailey had a small but extremely firm voice, not particularly high or low, which allowed her to have it both ways—to be demure and innocent when the material called for it and then to be hot and funky. Mildred Bailey is one of the primary colors of American jazz and pop singing. Thanks to her impact on Bing Crosby alone, we can say that many of the subsequent developments in jazz and pop were influenced by her.

The essential appeal behind Bailey’s art is the same that’s to be found in that of Louis Armstrong (earlier), Bing Crosby (concurrently), and Billie Holiday and Sinatra (later). They all understood that by swinging a number, a vocalist doesn’t necessarily have to strip the lyric of its meaning; that a good jazz singer can put a text over conceptually and dramatically while at the same time making it move. Armstrong had shown that jazz is essentially an art of spontaneity—or at least the appearance of spontaneity—and intimacy is a direct outgrowth of that. In jazz, the idea is to make it seem as if everything is happening right now, for the first time, on the spot. That ideal applies both to a trumpet solo that’s being improvised or a love lyric that the singer is making the audience feel she’s singing as if the words and the thoughts were occurring to her right then and there. This idea probably couldn’t have occurred without Armstrong, but it’s worth noting that even before the Great Man had recorded much as a singer, Crosby and Bailey were already helping perfect what Armstrong had begun.

As pianist Bill Miller put it, Bailey “knew how to ad-fib, I mean, she never quite sang anything the same way more than once. Maybe she wasn’t quite a jazz singer, but I wouldn’t know how else to describe her.”

In “I’ve Got My Love to Keep Me Warm,” for instance, hear how she puts the stress on the word “off,” which occurs twice in the bridge, as in “off with my overcoat/off with my gloves.” By accenting those two utterances of that key word, she gives each line an extra push, as if she’s kicking off into the water from the side of the pool. The rest of the line now has all the momentum it needs. She makes the lyric come alive. It’s a subtle thing, perhaps not even worth noticing among the dozens of interesting things that Bailey does with the words and music of the hundreds of songs she recorded in her career. Every record she made is loaded with masterful moments like that.

When, in August 1938, Down Beat asked Bailey to explain her style, she responded, “I don’t know exactly and I’ve tried to dope it out several times. The only answer I get is this: Sheet music was hard to get in my home town and a tune had to be learned [from] a recording or traveling band. It had to be memorized. I could never get the exact notes of a song, so I used to sit down and try to scheme out the best way to sing it smoothly. Sometimes I would think how a tune might have been improved if the composer had changed certain parts of the melody, and I would try singing it my own way. It sort of stuck this way through the years and before I could straighten myself out—I got to thinking I was traveling down the wrong trail—I found out that they were calling this ‘swing’ [quotations mine] and liking it!”

Bing Crosby later gave Bailey credit for giving him his start. Her relationship with him was crucial: When Crosby and Bailey’s kid brother, Al Rinker, came down to Los Angeles and camped on her doorstep, Bailey was then an established singer there. She helped the boys find work (actually, she and Crosby were the same age) and they succeeded wildly, so much so that a few years later “the boys” were able to do something for her. When in turn they helped her join the Whiteman band, it was the start of a lifetime of Crosby doing what he could for her. As popular as she was in the 1930s, neither she nor anyone else came anywhere near him. One can only imagine how Bailey, whose self-esteem issues went hand in hand with her weight problems, must have felt when, for instance, the latest Bing Crosby movie would come out and the best she could do was to sing songs from the score. When she was sick and broke at the end, Crosby helped defray her hospital expenses and gave her a guest spot on his radio show, which turned out to be one of her final performances.

But from the evidence on hand, we can only surmise that if Bailey could have hooked up with a major band or begun recording in 1926 instead of 1929, what we know of the development of pop and jazz singing might be quite different. Many of the innovations rightfully credited to Crosby—his intimate, direct way with a lyric, his incorporation of jazz techniques into the love song, his cultivation of the microphone and the mass media to create a newer, more immediate relationship between performer and audience—must also have been deployed by Bailey during the mid-twenties. We can assume that she was, as Crosby himself averred, a direct influence on him, as opposed to the hundreds of subsequent singers who learned these things from him. (Speculating from the opposite point of view, if either Bailey or the equally corpulent Kate Smith had come along twenty years later, in the age of TV rather than radio, it’s unlikely that either one of them would have made it at all.)

In her own time, Bailey didn’t need any “might-have-been” mentality. In the thirties, when Bennett and Clooney were kids first discovering the great bands and singers via the medium of radio, Mildred Bailey was one of the biggest stars on the air. By the late forties, through, her moment had long since passed. The postwar years were the period in which pop singers came to dominate the musical marketplace (chief among them being Clooney and Bennett, who both became recording icons thanks largely to Bailey’s onetime associate Mitch Miller). But Bailey had been a national name, especially in the early years of the swing era, first as vocalist with the biggest band of the Jazz Age (led by Paul Whiteman, a leader even more physically imposing than she was) and then as co-leader and featured star with one of the great ensembles of the swing era. Paradoxically, when her fellow singers, many directly inspired by her, began usurping mass-market popularity from the bands after the war, Bailey’s star began falling rather than rising.

By the time Clooney and Bennett hooked up, Bailey had already assumed the position she would maintain in death. Although she was no longer a force in the pop industry, her work was nonetheless cherished by the cognoscenti: the jazz press, lovers of the Great American Songbook, followers of the great jazz and pop stylists, musicians, and, most of all, other singers. Nearly all of them cited her, particularly Sinatra, who was not only deeply moved by Bailey’s singing itself but was also inspired by the way she was backed in the dozens of sides she cut with her husband Red Norvo’s orchestra. Yet except by these insiders, Bailey was almost completely forgotten at the end of her own lifetime.

Bailey’s glory years were the thirties, and her richest period is those years with the Norvo orchestra, from 1936 to 1939. Her output in this brief period is as large as the lady herself, and though collectors had to wait a long time, her complete catalogue is currently available on CD, which is fortunate in that virtually every record she made—especially in these years—is worth owning. A list of some of the other talent involved reveals the high regard in which Bailey was held by her colleagues, starting with producers Jack Kapp, John Hammond, and Morty Palitz, and extending on to the biggest names of that era, starting with Benny Goodman, Coleman Hawkins, the Dorsey brothers, and Artie Shaw. Indeed, it’s hard to think of a major figure or jazz faction of the era who is not represented here on some level. Even though Duke Ellington and Count Basie didn’t personally record with Bailey, major sidemen from their orchestras appear on her sessions, which should be taken as a sign of Ducal and Countal approval.

With the possible exception of Billie Holiday (who could to a degree even be considered Bailey’s own discovery), Bailey was the most consistent and prolific female jazz singer of the thirties, and the competition was formidable. For starters, there was the prodigiously gifted Lee Wiley (who only recorded sporadically in these early years; her own great work was to come later), Connee Boswell (the early thirties work both with and without the Boswell Sisters is the most outstanding; the later solos aren’t always as consistent), and Ella Fitzgerald (a contender certainly, but not yet what she would become). Apart from Holiday, none of them could match Bailey’s amazing output for either quantity or quality. No understanding of pop and jazz singing can be considered complete without factoring in Mildred Bailey.

“As far back as I can remember, I sang,” Bailey herself wrote in a brief autobiographical article in the early forties, “sang at school, at church socials, sang every place and every time I got a chance.” She was born Mildred Rinker in either 1901 or 1903—a date also given as 1907—the first of four children (including Alton “Al” Rinker) who grew up on a farm in Tekoa, Washington. Her father was of Swiss-American stock and her mother was part Coeur d’Alene Indian (giving her something in common with Lee Wiley, Kay Starr, and Keely Smith, who all had Native American blood in them). As Richard Sudhalter has observed, Coeur d’Alene traditions enabled Bailey to move between the head voice and the chest voice with far more ease than most vocalists. She studied piano and then voice at school, but left home early to escape an evil stepmother.

“As soon as I was old enough, it seemed only natural to go to work singing and playing the piano at Eiler’s music store in downtown Spokane,” continued Bailey, who also worked in the music department of her local Woolworth’s. “Eiler’s music store had a record department, and that’s where I first heard jazz bands. I’ll never forget the kick I got when I first heard ‘Tin Roof Blues’ by some unremembered orchestra, or the thrill when Bessie Smith arrived in a batch of race records. From then on, I couldn’t get enough of Bessie Smith and Mamie Smith, and I still can’t. They didn’t have sheet music for that kind of song at Eiler’s, but I wrote away to Clarence Williams and other music publishers in New York and got my own copies of songs like ‘A Good Man Is Hard to Find’ and ‘After You’ve Gone.’ ”

After working in the music stores, Bailey began to get work singing in Seattle nightclubs, which after the coming of Prohibition in 1920 became speakeasies. Local bandleader “Tiny Burtnett heard me and hired me to sing with his Butler Hotel band,” Bailey recalled in 1932. “I set out for San Francisco, where I was working in Marquand’s Cafe on the beach.” Before leaving Washington, she had met and married—and then un-married—a Spokane merchant named Ted Bailey, keeping his moniker as her showbiz name. Her second husband was one Benny Stafford, another enterprising soul, who managed to keep the healing waters flowing even though the stuff was now prohibited. Before long, she was firmly established in joints up and down the West Coast. At one point she played through her hometown, Spokane. Her little brother Al was too young to get in (apparently even speakeasies had a sense of propriety), but his new, older friend, Spokanite Bing Crosby, did attend and was mightily impressed.

In fact, inspired by Bailey’s success along “the circuit,” Al and Bing, already singing professionally around town, decided to try to make the big time in Los Angeles. First they bunked with Bailey, who helped them get started, and within a year or so they attained the upper echelon of showbiz when they were hired to sing with Paul Whiteman’s orchestra, the leading pop music aggregation of the entire era. Eventually, as we’ve seen, they were able to return the favor by encouraging Whiteman to hire her—making her the first full-time female band singer.

Bailey worked for three years with Whiteman, but their collaboration was hardly as magical or triumphant as Crosby’s relationship with the bandleader. Perhaps because female band singers were such an anomaly, it took Whiteman forever to finally get around to letting her sing on his record dates. Even then, the Whiteman-Bailey sides contain no masterpieces on the level of the best Whiteman-Crosby sides. Bailey and Whiteman ultimately parted company on unfriendly terms, and, unfortunately, the music industry seems to have taken Whiteman’s side in the professional fracas—the split didn’t do anything for her reputation.

She made her first record in October 1929, with a group of Whitemanites under the leadership of guitarist Eddie Lang. It’s a wonderful, ebonically driven Hoagy Carmichael aria (featuring Hoagland on piano) called “What Kind o’ Man Is You,” and that this recording is virtually its only hearing somehow makes it even more special. Rather than just running through a chorus, Bailey is given a full verse to sing in addition to the refrain, itself a rarity on a twenties dance disc. There are a couple of places where she lets notes ring like an old-fashioned, twenties-style singer, yet it’s also a harbinger of things to come at the end when she utters her final declaration of the title phrase, “What kind o’ man is you?” She presents it in a declarative fashion that goes outside the melody, just steps right out of the song in order to emphasize it—it’s a quite remarkable move that anticipates the future, and not just of Bailey’s own work.

Her’s first “solo” session, done in 1931 with the Casa Loma Orchestra, also shows her at an early pinnacle; Benny Carter’s “Blues in My Heart” reveals that, if one is seeking an amazing combination of blues and Tin Pan Alley aspirations, the singer to beat is Mildred Bailey. The sides with Whiteman, which actually came after the Casa Loma session, have some interesting moments, but there’s nothing as exciting as the consistently exciting sides she cut in 1933–34 with the Dorsey Brothers’ band and Benny Goodman. Both she and Crosby at this time were assigned a disproportionate number of songs concerning themselves with African American and/or Southern life and/or religion. Writers like Willard Robison were trying to be more sympathetic to black people at the time, though to later generations their work doesn’t seem any less politically unfortunate than the old-time mammy songs of Al Jolson’s era. Bailey, however, makes such texts as “Harlem Lullaby,” “Is That Religion,” “Cabin in the Pines,” “Emaline,” and “Ol’ Pappy” ring completely true. (All of her early, pre-1935 recordings have been gathered on two compact discs on the TOM label, Sweet Beginnings and Band Vocalist.)

By the mid-thirties Bailey was an established radio star—never on the level of Crosby or Kate Smith, but still popular. In 1935 and 1936, she began the most prolific period of her career, working in two distinct formats, which are best characterized as collaborations with two very different musical visionaries: producer John Hammond and her personal-professional partner, Red Norvo. Virtually all of her classic sessions were done for the ARC and Columbia labels, and are included on the essential ten-CD set The Complete Columbia Recordings of Mildred Bailey, released in 2000 by Mosaic Records. (If Mosaic had waited five years, they could have included the Whiteman sessions, too, which are now controlled by the Sony-BMG conglomerate.) Mosaic presented all the material chronologically, which makes sense, but they could just as easily have divided it up and put all the Bailey-Hammond sessions together and the Bailey-Norvo sessions somewhere else, even though there’s a fair amount of crossover between the two groups of recordings.

John Hammond spotlighted Bailey in a series of sessions similar to those he was overseeing simultaneously with Billie Holiday: loose, informal small-group sessions with lots of great soloists and something of an intimate feel. Over the years, soloists like Roy Eldridge regularly turn up on her dates, while there are also special sessions with a bunch of Count Basie–ites (including Buck Clayton and Herschel Evans) and various Benny Good–men. Pianist Teddy Wilson, who was also a regular (and frequent leader) on the Holiday series, was Bailey’s favorite accompanist.

There’s an especially wonderful session from November 1936, with Ziggy Elman, Ben Webster, Teddy Wilson, and Artie Shaw, which yielded another marvelous sample of ebonics, “ ’Long About Midnight,” one exceptional new song, “It’s Love I’m After,” and a terrific reading of “More Than You Know,” already a standard with jazz credentials (Goodman had cut it a few months earlier). In January 1938, Bailey did a session that’s remarkable even by her very high standards, co-starring Chu Berry, drummer Davey Tough, and Wilson. She establishes Schwartz and Dietz’s brand-new “I See Your Face Before Me” as a future jazz standard and finds even more pathos than Bob Hope does in “Thanks for the Memory.” Most remarkable is what she does with two longhair items, “From the Land of the Sky Blue Waters” and “Lover, Come Back to Me.” The first comes from the tradition of “serious” concert music, the second from operetta. Bailey was the first heavyweight jazz singer to invade either field, and while she inaugurated only a brief vogue for swinging “Sky Blue Waters,” she turned “Lover Come Back” into a perennial for jazz singers and players.

In 1932, Bailey had married xylophonist and composer Red Norvo, the first major jazz virtuoso on his instrument, and at the time a star soloist in the Whiteman organization. Between 1933, when they jointly left Whiteman, and 1936, Norvo gradually worked out a style and a sound for his own dance orchestra. The band’s slogan was “soft, subtle swing,” meaning that even though it swung like crazy, the Norvo band wasn’t screaming in your face like the average post–Benny Goodman big band. Sometimes the two were billed jointly as co-leaders—appropriately as “Mr. and Mrs. Swing”—but even when they weren’t, Bailey’s name was prominently bannered as the band’s star attraction. She sang on the vast majority of the Norvo band’s recordings, some of which were released under her name.

Norvo and Bailey complemented each other beautifully—they were one of the best partnerships in jazz, like Reinhardt and Grappelli, Beiderbecke and Trumbauer, Holiday and Young. She had a light, mid-range sound, and his jazz ensemble depended for excitement neither on exaggerated dynamics nor a particularly wide harmonic range. Together, Mr. and Mrs. Norvo were potentially the great power couple of jazz, and the music business held high hopes for the success of their band, hopes that were realized artistically, though not, in the long run, commercially.

The third contributor to the overall excellence of the band was the brilliant, far-sighted arranger Eddie Sauter, who further ensured that the Bailey-Norvo combination would never sound like anything else in jazz. The very first session by the newly established Norvo-Bailey band includes “Smoke Dreams,” an average pop song that Sauter and Bailey elevate to Olympian proportions. His orchestration is a complex grab bag of twentieth-century classical music, including polytonality and various approaches to dissonance. For her part, Bailey makes the song work by swinging it as simply and sincerely as possible and singing it so vividly that you, too, begin to see hallucinations in a campfire.

The sides released under Bailey’s name originally appeared on Brunswick, whereas the sides with Norvo top-billed were first issued on Vocalion. The division was quite random: Two of Bailey’s very finest and funniest features, “Weekend of a Private Secretary” and “Arthur Murray Taught Me Dancing in a Hurry,” were both released under Norvo’s name. She sings all the way through—she’s not confined to a 32-bar vocal refrain—and each number amounts to a fairly sophisticated yet swinging comedy monologue by Johnny Mercer. As I’ve mentioned, the Hammond-produced sessions and the Norvo-centric dates were not rigidly segregated: Norvo and his sidemen often appear on the Hammond “jam session” dates, along with members of the bands of Basie, Goodman, and even Ellington.

After the Mr. and Mrs. Swing band broke up in 1939, Bailey herself was still popular enough to keep recording for the ARC corporation as it evolved into the newly reactivated Columbia Records. With Hammond and other producers, she continued to find new and interesting formats to work in: There are twenty or so titles she sings with the remarkable John Kirby Sextet, and another, equally productive, series of sessions in which she’s accompanied by an ensemble inspired by Alec Wilder’s chamber octet. Sauter continued to serve as her musical director on both of these projects—the first featuring predominantly black musicians (but also showcasing Norvo), the second primarily white players (as well as Roy Eldridge and the beloved Teddy Wilson)—and both utilized orchestrations that, as was Sauter’s wont, combined jazz and classical elements. Around the same time, however, Bailey joined forces with Mary Lou Williams and a group of sidemen from Andy Kirk’s Clouds of Joy for a session that consisted entirely of songs based in the blues, as if she wanted to prove that she hadn’t lost touch with the music’s roots. She and Norvo reunited occasionally on records as late as 1945, even though by then they were no longer Mr. and Mrs. anything.

Bailey’s great years as a recording artist were the thirties, the period right before, during, and immediately after the glory days of the Norvo band. In the early forties, the combination of the ASCAP ban against radio stations (1941), the American Federation of Musicians strike against the record labels (1942–44), and the war upset everybody’s apple cart, not just Bailey’s. In fact, she was still quite visible—or audible—on the radio for the duration. There are ten first-class sides done for Decca in 1941–42, some of which, like her Sauter-Wilder-Chamber sessions of 1939–40, use a black gospel vocal group for backing. (These sides are gathered, along with some earlier and later items under MCA’s jurisdiction, on The Rockin’ Chair Lady.) One positive outcome of the war situation was a 1943 duet date with Teddy Wilson waxed for the army V-Disc program, which includes a tremendous “Sunday, Monday or Always” and perhaps her tenderest reading ever of her theme song, “Rockin’ Chair.”

From June 1944 to February 1945, Bailey headlined in a weekly radio program called both Mildred Bailey and Company and Music Till Midnight. The thirty-four programs featured not only the singer with an all-star, interracial orchestra (practically a first for radio) but—between guest stars and regulars—many of the finest and biggest-name instrumental stars of the swing era. CBS presented the shows live on civilian radio, but the show was also planned as a source of material for V-Discs and the Armed Forces Radio Service. It was certainly Bailey’s finest hour, radio-wise. (The shows were rebroadcast on NPR in the seventies and early eighties, and occasionally one hears a rumor that a label like George Buck’s Audiophile will issue the series complete on CD, which would certainly be a major mitzvah.)

Which makes it all the more surprising that Bailey was not given a contract with a major label when the war was over. Instead, she cut her last date with Norvo in 1945, the same year they were officially divorced, for the tiny Crown label (John Kirby and Sarah Vaughan were recording for that company around the same time). Old friend John Hammond was then running the jazz and pop division for the equally diminutive Majestic Records, and made about sixteen sides with her, many conducted and arranged by Eddie Sauter, her most consistent and prolific recordings outside the Columbia/Mosaic package. The Majestics include some of her most poignant ballads, “You Started Something” and “I’ll Close My Eyes”; her funniest novelties, “A Woman’s Prerogative” (from St. Louis Woman), “All That Glitters” (a rather scathing calypso); and her two alltime greatest show tunes, “Almost Like Being in Love” and “The Heather on the Hill” from Brigadoon. (The most recent issue of the Majestic material is a Denon CD entitled Me and the Blues, an import well worth seeking out.)

Bailey was clearly still close to the peak of her powers in 1946–47, as also evidenced by a rare single on RCA, Nat Cole’s “That Ain’t Right,” and her last Willard Robison song, “I Don’t Want to Miss Mississippi.” During this period, pianist Ellis Larkins—who would eventually prove himself with Ella Fitzgerald and Lee Wiley, among others, as one of the finest accompanists of all time—serves as a worthy replacement for Teddy Wilson.

Though she was singing as well as ever in the mid- to late forties, her health was beginning to fade. After the demise of the Norvo band, she was never quite strong enough to tour so extensively again. Her health hadn’t been good throughout her whole adult life, and the rigors of the road had been especially rough on her during the years she was trying to help make her husband’s big band a success. Encyclopedist Roger Kinkle reports that she was seriously injured in a car accident sometime in the mid-thirties, but even if that isn’t true, her health seems to have been in a downward spiral throughout the forties.

She did, however, land some major gigs in New York: the Bon Soir (around 1946) and Cafe Society (June 1948). At that point, Time magazine gave her a huge rave review: “Not a pound underweight (at 190), in a shroud-like black gown, her swarthy features and shoe-button eyes gleaming in the spotlight.” But that was about it. Gradually she was less and less able to work, and began spending more time at her farm in Poughkeepsie, New York. (As jazz scholar Phil Schaap has revealed, she kept up with the new music—even as Norvo did. At a March 1949 broadcast by the Charlie Parker Quintet, emcee Symphony Sid spots her in the Royal Roost and announces her to the crowd.)

After one particularly rough bout with illness, she appeared on the Philco Radio Time program (with Bing Crosby, who refers to her being on “the sick list”) and Refreshment Time with Morton Downey, like Crosby a friend from the Whiteman days. “I really got a big lift out of doing that radio show with Bing,” she said in Down Beat (June 1950, probably her last mention in that magazine during her lifetime). “That man makes everybody feel good who works with him.” She also added, “Now that I’m beginning to feel good again, I’m looking forward to some really happy sessions under my new contract with Decca.” Unfortunately, that contract would only lead to one session, her last, on April 25, 1950 (“Cry Baby Cry” and “Blue Prelude”) in which she ominously and presciently anticipates her “last go-round.”

Bailey had long since stopped supporting herself: Frank Sinatra, whom she had never met, and Bing Crosby paid her hospital bills, and Crosby paid off her mortgage. She died on December 12, 1951, at home in Poughkeepsie, not long after collapsing during an engagement in Detroit.

“One time I was doing a jazz concert and they asked me to sing ‘Rockin’ Chair,’ ” Lee Wiley reminisced shortly before her own death in 1975. “Well, I did sing it, and right in the middle I started crying, because it reminded me too much of Mildred. When she died, I wrote a card with the orchids I sent and I said, ‘To the greatest of them all.’ I think that sums up what I thought of her.”

Pearl Bailey (1918–1990)

There’s a little bit of Pearlie Mae in all of us, and there’s a lot more to this Pearlie Mae gal than immediately meets the eye. She wants the same trappings of wealth and luxury that the rich folks and the high-class folks have, those fancy cars and apartments, furs and jewelry, power and security, yet at the same time, the allure of respectability and a life of luxury may not be enough to entice her to give up what we might call those baser pleasures—high-living, raising the devil, and just plain old jelly roll. Pearlie Mae must continually balance her lust for social climbing against her more deeply rooted lust for lust.

As created and performed by Pearl Bailey, Pearlie Mae is a deep and complex character, drawn in both intricate, subtle lines and bold, dramatic brushstrokes. Like the best ethnic performers of any era, she spoke both to and for the rest of her group. She not only communicated the feelings of her own people in the postwar era, and women in particular—and did so in a way that they could laugh at—but articulated those concerns so that the larger public beyond could understand them, too.

“St. Louis Blues,” which she recorded several times, is a traditional air of woman’s suffering, but she makes W. C. Handy’s tune jump in the doubletime Louis Jordan–Tympany Five manner so effectively that she divests it of its usual self-pity. When singing “Tired”—the number most associated with her in the early days—in her first film, Variety Girl (1947), she could easily have been dressed in a maid’s uniform while she sang, like practically every other black woman in Hollywood history up to that point. But she and Paramount did their own little bit for human rights when they made Pearlie Mae a housewife, singing with an ironic twist about the same frustrations and yearnings that all women were (and still are) feeling.

From a broader perspective, it’s remarkable that Bailey, who is rarely given credit for being the exceptional singer she was, was actually able to create a consistent character in song—something that few popular or jazz singers were able to do. “Tired” contains a spoken interlude in the middle, in which Pearl refers to a psychiatrist as “one of them rich people’s doctors,” and such observations were essential elements of Bailey’s art. “When I’m called a great ‘singer,’ I always disagree,” she wrote. “I think of myself as telling stories in tune to music. The words become very important, and that I love. And it doesn’t hurt if you’ve lived a bit, too.”

As with the best popular art, there’s a timelessness to her very timeliness. Bailey’s spiels not only anticipate the entire current rap movement, they exceed it. “Legalize My Name” resounds as a more substantial “Justify My Love” of the forties. “Legalize” is Arlen and Mercer’s answer to the traditional spiritual “Scandalize My Name,” which Louis Armstrong had already updated in his 1941 “Do You Call That a Buddy?” When Pearlie Mae insists that her errant swain bring her before a justice of the peace, she makes sure he spells it “peace” and not “piece.” (If you know what I mean, child. Have mercy!)

A gifted singer and a fine actress, Pearlie Mae Bailey put it all together in a manner reminiscent of shamanism. A storyteller who tapped into a tradition as ancient as campfire folklore and as up-to-date as bebop, Bailey put over a series of narratives through a combination of music and speech; as with her close friend Nat King Cole (with whom she co-starred in the film St. Louis Blues), both the message itself and the methods of its expression were equally remarkable. From the beginning of her career—the dozens of excellent sides she cut for Columbia and Harmony Records in the postwar era—Bailey artfully turns monologue into music and back again. The best aspects of both conventions are clay in her hands, waiting to be forged into 100 percent genuine pearls by the force of her charisma, overpowered by her personality even when she’s characteristically relaxing.

Bailey sold her music short when she said, “My hands are my words.” I never saw her work live in concert, and I imagine she must have been wonderful, but she mastered the recording medium fairly early, and enjoyed a consistently excellent album and singles career. Pearlie Mae uses inflections and asides (such as “Have mercy!”) like no one else, with the possible exception of her onetime mentor, Fats Waller. At times she exaggerates an idea as outrageously as a cartoon character (or even as Fats Waller), and yet she also is the master of understatement (as when, on “Tired,” she compares her looks, after a day of washing, to Hedy Lamarr), rambling, and what they used to call rabulating—not to mention signifying, shucking and jiving, putting us on—to get her message across.

As was true of Ethel Waters, her diction and articulation are generally razor-sharp and impossible to misunderstand, but then, like Marlon Brando, she is also the master of the mumble. Nobody else—with the possible exception of Bob Hope—can make a punch line seem more funny by burying it under his breath. No one else can score equally well with the most rudimentary blues and with the most sophisticated—or faux-sophisticated—lyric by Cole Porter or Lorenz Hart. Other people have sung Porter’s “Josephine” from Silk Stockings (Janis Paige in the movie version, for one), but only Pearlie Mae makes it sound completely natural that Napoleon’s future bride “Tripped away to Paris France/In her ye olde Creole fancy pants.”

When she wants to play it cute, as on the classic Burke and Van Heusen Road movie song “Personality,” the title word gets sung rather than spoken directly because Ol’ Pearl wants you to think twice about what it means (and how it also reflects back on the singer: “The madam has the cutest [pause] personality”). On “Legalize My Name” and “A Woman’s Prerogative,” her two showstoppers from St. Louis Woman, she plays the game of half-understanding and half-mispronouncing all those humongous twenty-dollar Noah Webster gems, trying to find some legal and social justification—or as she says, “precedent”—to have it both ways. She can make her man march to the altar when she says “Forward!” Conversely, when some possessive male tries to tighten the screws on her, she’s always got an exit strategy.

Pearl Bailey was born in Newport News, Virginia, on March 29, 1918 (slightly less than a year after that city’s other major contribution to world culture, Ella Fitzgerald); she grew up in Washington and Philadelphia. Bailey began singing for audiences in Washington’s Jewish neighborhood in the very early thirties, and had her first taste of a career because of inner-family reverse psychology. Her brother, Bill Bailey, was a rising dance star (according to one old showbiz story when he got into trouble with the law later on, a judge very somberly pronounced, “Bill Bailey, you ain’t goin’ home!”) who ordered his little sister to stop following him around backstage. Just to get back at him, she entered an amateur contest being held at the theater where her brother was working, and won.

For the next decade the young Pearl scuffled across the country, working as both a dancer and a singer. “Singers should learn to dance,” she said later; “then their phrasing would be smoother and their body movements would synchronize with the phrasing.” She gained valuable experience in the chorus line of Noble Sissle’s Shuffle Along (the most popular all-black show of the interwar era, productions of which stayed on the road deep into the thirties). She also entered into and summarily exited from a quickly forgotten first marriage while hoofing in the Pennsylvania coal circuit. She worked as a band vocalist with Harlem-based Edgar Hayes and just missed a chance to work with Count Basie (her brother, Bill, headlined with Basie at the Orpheum in Los Angeles in 1943, and she appears with the band on a 1945 aircheck).

In late 1943 and early 1944, she worked with former Ellingtonian and Goodmanite trumpeter Cootie Williams, then leading his own orchestra. This was a band full of future stars, nearly all with nicknames (perhaps inspired by the leader), Earl “Bud” Powell, Eddie “Lockjaw” Davis, Eddie “Cleanhead” Vinson, and Bailey. There was a recording ban going on, but by a fortuitous set of circumstances, at the time Williams was recording for Eli Oberstein’s Hit Records, and that enterprising entrepreneur wasn’t about to let a little thing like a labor union stop him. Hit released two Bailey-Williams titles, “Now I Know” and “Tess’s Torch Song,” both written by Harold Arlen for Dinah Shore (who couldn’t record them herself because of the ban) in Danny Kaye’s first film, Up in Arms. “Tess’s Torch Song” was actually better suited to Bailey than Shore, both for its blues undercurrent and the way its narrative suited her half-singing, half-spieling style. Bailey helped make “Tess’s Torch Song” into a hit, even though the Hit Records label was not widely distributed. While touring with Williams she also met the brilliant arranger Don Redman, one of the founding fathers of the entire swing era and her future musical director.

“Oh, ambition was mine when I was young,” she later said. After Cootie Williams, Bailey joined a USO tour, and recorded several tunes for V-Disc in late 1944, backed by jazz stars Herman Chittison (piano) and Charlie Shavers (trumpet). “The Quicker I Gets to Where I’m Going” illustrates Bailey’s evolving earthy narrative style, underscored both by a bluesy feeling and wartime patriotic sentiment. As a single, she also sang in an L.A. club operated by former Ellington vocalist Herb Jeffries, and in 1944 she had a guest shot with violinist Stuff Smith on an obscure independent label. She had already begun to catch on with the smart set at New York’s Village Vanguard and Blue Angel when she finally got her big break with the public at large in 1945.

Cab Calloway and His Orchestra were headlining at the Strand Theatre in Times Square, and Sister Rosetta Tharpe was set as the featured female vocalist. When the good Sister took sick, Bailey got the call to fill in. She strutted out and treated the customers to “Fifteen Years,” “Straighten Up and Fly Right,” her specialty, “Tired,” and, for an encore, “St. Louis Blues.” “I heard something perhaps I’d never heard [before],” Bailey later remembered. “It was applause, real. Thunder and lightning, and all the elements spoke at once. The next thing I knew, I was walking to the far corner backstage and someone said, ‘Where are you going?’ and I said, ‘Over to that corner—to pray.’ ” She remained with Calloway’s troupe for a spell at the posh Zanzibar Club on Broadway (two decades later she and “The Mighty Calloway,” as she called him, would headline together again in Hello, Dolly!—also on Broadway).

Following her success with Calloway, Bailey went national and then international with the Broadway show St. Louis Woman. The show itself was far from a hit: The Harold Arlen–Johnny Mercer score was absolutely tops, but the NAACP and a lot of other people objected to the outdated portrayal of blacks in the script, and Annie Get Your Gun was a blockbuster hit that blasted away all the competition that season. Yet St. Louis Woman was a triumph for Bailey herself: “Lucky duck me had the two showstoppers, ‘Legalize My Name’ and ‘A Woman’s Prerogative,’ ” she remembered. In fact “Any Place I Hang My Hat Is Home” and especially “Come Rain or Come Shine” have both become standards, recorded by dozens of other artists, but precious few other female singers have had the nerve to try to compete with Bailey on those first two songs. (The only one who comes even close to out-Baileying Bailey is the older Mildred Bailey on “A Woman’s Prerogative.”)

Around the time of Bailey’s Broadway debut, Manie Sachs signed her to Columbia Records. By this time, she was connected to the worlds of jazz, Broadway, and pop, and her Columbia sides of 1945–50 utilize a succession of perfectly chosen small groups, all consisting of inspired soloists and studio men who had cut their teeth in the swingband era.

But—as Bailey would sing just a little later on in her career—it really took two to tango. The best of Pearlie Mae’s early sides are her duets, which allow her to more fully balance speech and song and just plain carryin’ on. Columbia combined her with its number-one male artist, Frank Sinatra, for the two-sided 78 “A Little Learnin’ Is a Dangerous Thing,” believed to be the first interracial duet ever recorded (even preceding Louis Armstrong and Bing Crosby’s commercial collaborations), which unfortunately led to its obscurity, as it had to be specially ordered even in shops that normally carried all of Bailey’s and Sinatra’s latest Columbia waxings. There were several titles with the much loved black comedienne Jackie “Moms” Mabley, most notably on Louis Jordan’s “Saturday Night Fish Fry.” Mabley was never to make much of an impression as a vocalist, but in back-and-forthing with Pearlie Mae here, she more than justifies Bailey’s description of her as “the funniest woman alive—no script but her own.” In the early seventies, Bailey would assume Louis Armstrong’s role on the famous Bing Crosby–Louis Armstrong duet on “Gone Fishin’.” (YouTube makes available a lot of amazing TV duets between Bailey and Carol Channing, Dinah Shore, and others.)

Bailey was so nimble-footed and quick-tongued she inevitably ended up outshining her co-stars, and the records boosted her career but not theirs. Her most formidable partner and adversary was the outstanding trumpeter and vocalist Hot Lips Page, who duetted with her on one of the best of all boy-girl recordings, “Baby, It’s Cold Outside”—a strong contender for the title of history’s all-time jive duet classic. This was despite steep competition: Frank Loesser wrote the words and music as a party piece for himself and his wife, and it was also recorded commercially by the teams of Margaret Whiting and Johnny Mercer, Louis Armstrong and Velma Middleton, Sammy Davis Jr. and Carmen McRae, and Ray Charles and Betty Carter. In the MGM movie Dangerous When Wet, it was sung by two teams: romantic leads Esther Williams and Ricardo Montalban, and comedy couple Red Skelton and Betty Garrett, who (even though Garrett was the only one of the four who could actually sing) were enough to earn “Baby” the 1949 Academy Award for Best Song.

Columbia’s A&R staff liked the song so much that they cut it twice, once on the main Columbia label with Buddy Clark and Dinah Shore and then again in the definitive rendition, by Pearlie Mae and Hot Lips. Their Oxford gray version was issued on Columbia’s subsidiary label, Harmony Records, which explains why, when Hot Lips pleads “(Let me) put some records on while I pour,” she inquires, “Harmony records?”

Bailey was so successful in terms of rhythm and comedy that Columbia downplayed her ballad singing: Two of her best straight-ahead love songs (with no spieling or humor), “They Didn’t Believe Me” and “Here You Come with Love” were not issued until the CD era. It will no doubt come as a surprise to those who know Pearlie Mae only as a spieler and homespun philosopher that she could also turn on the tender—and so effectively.

Bailey’s parting gift to Columbia Records was helping to discover Tony Bennett, whom she installed in a Greenwich Village revue (she was the headliner and mistress of ceremonies) and introduced to Bob Hope—to this day Bennett gives her credit as the mother of his career. In 1950, she switched from Columbia’s Harmony subsidiary to Decca’s relatively new Coral subsidiary. Her backing bands got bigger, less jazzish, and more poppish, but with astute arrangements by Don Redman. She landed a hit in “Two to Tango,” which she followed up with other quasi–South American items (including another tango, “I Love My Argentine,” and “Sing Something Special,” not to mention “Perandez from the Andes”). She also acquired a husband who would stick with her for the rest of her life, the star drummer Louis Bellson. The superb percussionist was at the time with Duke Ellington, and he would spend the next forty years alternating between leading his own groups and serving as his wife’s musical director. In 1954 she would reteam with Harold Arlen for another unsuccessful show with a great score, A House of Flowers. Redman served as orchestrator here, too, and Bailey, by the evidence of the original cast album, stopped the show with Arlen’s beautiful “Don’t Like Goodbyes.”

At around the same time, Bailey recorded two albums for Mercury, The One and Only Pearl Bailey (which was subtitled “…  For Adult Listening”) and The Intoxicating Pearl Bailey, but she would come into her own as an album artist at Roulette Records. She seems to be the first of many great African American entertainers who worked on Roulette (Count Basie, Sarah Vaughan, Billy Eckstine, and Dinah Washington came later), and the label’s strategy regarding her was unique: Roulette seems to have taken the low road and the high road at the same time with her. Much of her output was, as on The One and Only, “…  For Adult Listening.” It’s not as if they were trying to sell her as a low-rent purveyor of “party records” (like Rusty Warren, who sang about knockers and dingies, and whose records were generally buried deep in closets where kids inevitably found them). Mostly everything on Bailey’s “adult” records is perfectly clean; the lure for adolescent listeners may well have been the mere implication that something here may not be suitable in the Tipper Gore household. The One and Only even framed her picture on the album cover with the giant shape of a keyhole.

Other albums that dwell on this theme (all on Roulette) include Pearl Bailey a Broad (a set of travel-related songs), For Adults Only, More for Adults Only, Songs of the Bad Old Days, Naughty but Nice (which includes something titled “Since I Became a Hussy”), All About Good Little Girls, The Risque World of Pearl Bailey, and For Women Only, among others. Compared to the rampant salaciousness of later generations (not to mention the explicit blues numbers of the twenties and thirties) these records are fairly tame in terms of satisfying those who would buy them for a cheap thrill. But they are decidedly “adult” in that they feature intelligent, often classic pop numbers sung intelligibly for a grown-up sensibility. There’s nothing for kiddies here; in fact, she disses the entire teen idiom in a very funny (albeit untrue) specialty number titled “I Can’t Rock and Roll to Save My Soul.”

While the “adult” albums had a specific audience, Roulette also promoted Pearl Bailey as their approximate equivalent of Ella Fitzgerald in a series of songbook albums that numbered at least four: Pearl Bailey Sings Porgy and Bess and Other Gershwin Favorites, Pearl Bailey Sings Songs She Loves by Her Favorite Composer Harold Arlen, St. Louis Blues (the songs of W. C. Handy), and The Songs of Academy Award Winner James Van Heusen. For her Cole Porter album, she combined the high and low strains of her talent by concentrating on Porter’s saucier material, a very wide subgenre of his work. The Arlen album was an outgrowth of the two Broadway shows she had done with the songwriter, while the Handy and Gershwin projects were tie-ins with two of her movies, St. Louis Blues and Porgy and Bess.

Mysteriously, none of this material is on American CD reissues (although there is a recommended three-disc package from France, Pearl Bailey: The Best of the Roulette Years, which totals fifty-four firstrate tracks). Yet the delights of the Mercury and especially the Roulette LPs are manifold. The Arlen set includes virtually the entire scores of St. Louis Woman and House of Flowers, including all the songs that Bailey didn’t do in those Broadway productions. The Porter package is highlighted by his parody “Josephine” and his ode to undies, “Satin and Silk,” both from Silk Stockings. Bailey is especially effective on Porter’s tale of those two social-climbing so-and-sos, “Mister and Missus Fitch”; only Pearlie Mae can get so high-toned and so gully-low all at the same time. She shows us what a “sophisticated” song, like one of Cole Porter’s, and a low-down blues number, like one of W. C. Handy’s, have in common.

The W. C. Handy collection has her sounding more like a genuine Delta blues singer than anywhere else in her career. In the film St. Louis Blues, Nat Cole sings a new Mack David song called “Morning Star” that was supposedly inspired by Handy, but on her Handy album, Bailey sings the actual Handy piece, “Shine Like the Morning Star,” a comparatively rough-hewn blues-gospel hybrid. The new version of “A Woman’s Prerogative” on the Arlen album is even better than the original, with Bailey literally growling and blasting out the text.

The Gershwin Porgy and Bess album is also very satisfying; the only disappointment is that Bailey doesn’t do “I Can’t Sit Down” here—this was her big number as Serena in the 1959 Otto Preminger film of the Gershwin opera (although she did sing it on the original sound track LP). The James Van Heusen album (which consists mostly of songs associated with either Crosby or Sinatra) uses a large and lavish string orchestra; contrastingly—and unusually—the Gershwin collection finds her accompanied by merely a rhythm section (sometimes just a piano) and a full, gospelly choir, billed as “The Voices of the Ambassadors.” The overall effect is to instill in the Gershwin canon a very down-home, churchy feeling, especially in “Oh, Lady, Be Good” in which the Ambassadors are reminiscent of the Charioteers, who had backed Bailey a decade earlier. The Roulette albums are a great body of work by a seminal entertainer, and they deserve to be more thoroughly explored in the digital era.

Bailey seems to have lasted longer with Roulette than any other artist, going up to the mid-sixties. She was more visible than ever in 1968. In that year she headlined on Broadway as Dolly Levi in Hello, Dolly!, in which her onetime boss Cab Calloway co-starred as leading man Horace Vandergelder, and she also published The Raw Pearl, her first of two books. She cut two new albums, one titled The Real Pearl, for Enoch Light’s Project 3 Records, for which she teamed up with arranger-conductor Marty Paich. Some of the tracks are a little too deep into the sixties idiom (like Burt Bacharach’s “A Tower of Strength”), but most are more tasteful than you might imagine they could get away with in 1968. The standout is one of the top “talking songs” of all time, Bert Williams’s “Nobody.” There are also two songs by Ervin Drake (the inspirational “I Believe” and the nostalgic “Ukelele Talk”), the only version of the Mercer-Rowles “Baby Don’t You Quit Now” that challenges Tony Bennett’s, and a very exciting, decidedly post-Sinatra reading of “That’s Life” (very Vegas, as you can well imagine). In 1971, she released an album called Pearl’s Pearls on RCA, with more good songs and an all-star team of arrangers (Benny Carter, Bill Holman et al.), whose charts were played by Louis Bellson’s big band.

Bailey never faded. She was more of a constant presence in the seventies than in any other decade, thanks to a TV series. She had always had a tendency for dispensing advice, and was a natural talker in a formal interview setting as well as in a song. While she was alive, Dick Ables, who worked as Louis Bellson’s New York band contractor and librarian, consistently described her as “the kind of woman that likes to run everybody’s life,” although he painted a considerably more genteel picture of the lady after she died in 1990.

In her fifty years of performing professionally, Bailey triumphed as one of the world’s best-loved jazz-influenced popular entertainers—a singer who was also a brilliant comedian and a comedian who was also a brilliant singer.

Chet Baker (1929–1988)

For most musicians, art is what you make on the bandstand and life is dealing with things like rent and relationships. Chet Baker had it the other way around: When he ambled up to the microphone, what came out of his trumpet or his mouth was life. His music was so natural and direct, it wasn’t even a reflection of his soul, but his soul itself. Nearly every portrait or profile of Baker describes him as a cipher, neutral, devoid of any personality but what came through in his music. His playing and singing were all that he was.

Baker had to work no harder to sound the way he did than he did to talk or look the way he did. So what did he do when he wanted to create art? He got lost. He went to Europe, got high for three weeks, disappeared on a boat somewhere, found a new girl, went flying off balconies, or all of the above. Getting “lost” was the only way Baker could achieve distance, a concept that was critical in his life and work. He could settle down with one lady love after another and yet not really be there at all. He could spill his guts out in a song and calmly pack his trumpet away at the end of a gig and call a cab.

He also seems to have had little appetite for looking at himself, his own pictures, listening to his records, or reflecting philosophically on the meaning of his existence. If so, he was the only one. Bruce Weber’s 1989 film Let’s Get Lost, produced with Baker’s participation but not released until after his death, is less about Baker himself than it is about the act of listening to him. The filmmakers spend much time with record producer Dick Bock (of Pacific Jazz) and photographer William Claxton. Later in the film, Weber takes his place in the celluloid catfight competition among the parade of Baker’s significant others that marches by. All who come into contact with Chet want to (1) save him from drugs and from himself and, failing that, (2) explain him to the world. Baker himself remained supremely uninterested in either goal.

All stories must have an ending—in a sense, Weber could not complete and release his film until Baker provided him with a finish. Ex–dope fiends, like other reformed sinners, from Saint Augustine and Jelly Roll Morton onward, can’t stop confessing. Art Pepper filled an excellent documentary and autobiography with loving nostalgia for his years as a junkie and criminal, as if talking about heroin served as a substitute for shooting it. Baker was still using the stuff, practically to the day he died, and thus had no need to talk about it.

Some critics seemed almost to resent his success—perhaps because he became a star in the big, mainstream world beyond jazz even before the jazz community had given him its seal of approval. Early writings about Baker try to impose a sense of guilt upon him, claiming that his “flaw was tragic in the classical sense” or that he was “fighting a losing battle with heroin.” It wouldn’t do to portray Baker for what he really was: a relatively happy, guilt-free junkie, one who, in terms of the quality and quantity (at least two hundred albums) of his recorded work, could hardly have been more productive. Nor did his art ever become complacent or stagnant: Baker was always eager to try new ideas, new combinations, and new compositions.

Playing or singing, Baker was a font of melody—he had more of it in him than virtually any other jazz instrumentalist or singer you could name—and he was more generous with it than most. Tunes of all sorts poured forth from his lips like water from a faucet. Improvising, Baker could simultaneously spin songlike lines that seem as fully developed as a Cole Porter song; singing or playing the written melody, Baker could put it over as movingly as Billie Holiday. His improvisations were so eminently singable that Susannah McCorkle even once put lyrics to his solo on “Look for the Silver Lining.” Baker just stood back and let it flow out of him, with what seemed like precious little forethought or even practice. Never was a musician’s passiveness such a positive component: It required no conscious effort either to create breathtaking solos or to maintain his identity in diverse contexts, whether as spare as the pianoless Gerry Mulligan Quartet or as overwhelming as a full symphony orchestra.

In a 1978 interview with Gudrun Endress of Jazz Podium magazine, Baker was asked how he was able to not think about all the “trouble” in his life when he was up on the bandstand trying to create beauty. “I just kind of had it in my head to try to put that part of me in a sort of unreachable place, you know?” Apparently, he never ran out of storage space in that unreachable place. Yet by all indications, his term for it was something of a misnomer—to Baker, the unreachable place was so easily within his grasp that he never once seemed to be reaching for it. Creativity and inspiration were almost always there and almost never failed him.

Baker didn’t so much make records as permit others to make records of him. And records and records and records, from his first recorded appearance (with Charlie Parker) and his breakthrough to international acclaim (with Gerry Mulligan) to a March 1988 performance claiming to be The Last Great Concert. Just in the eighteen months between his death in Amsterdam (May 13, 1988) and the end of the eighties, dozens of Baker packages were released, a number that twenty years later continues to mushroom.

Where does Chet Baker’s singing fit within his canon? It’s a tricky question. When he first established himself as a singer, he was anointed the most outstanding instrumentalist-vocalist since Nat King Cole and Louis Armstrong (presumably that includes Jack Teagarden and Fats Waller). As with Cole and Armstrong, there were ultimately two different audiences for his playing and his singing. And there’s no predictable response to his music: Jazz critic Nat Hentoff, hardly a specialist in songs and singers, pooh-poohs Baker’s vocalizing, whereas Rex Reed, who writes mainly about cabaret and musical theater (when he covers music rather than film), feels that Baker is one of the all-time great jazz singers. You would think their opinions would be exactly the reverse.

Baker’s singing found favor especially among Brazilian instrumentalist-composers like João Gilberto and Antonio Carlos Jobim, who discovered in him a role model in the craft of singing without a trained voice, and in how to get so much music and emotion from an inversely proportioned vocal instrument. Much of his audience wanted to hear him sing as much as they came to hear him play, yet he made surprisingly few vocal albums, especially in the later period, when someone was recording him almost weekly.

He was widely perceived as a creature of pure feeling and of pure instinct rather than of musical technique, and indeed he was not a schooled musician. As Dexter Gordon observed, Baker didn’t know the first thing about what key he was supposed to be playing in, “but when he started playing, it was so natural and so beautiful.” Drummer Larry Bunker once told Ted Gioa how Baker would struggle with trying to read one of collaborator Gerry Mulligan’s orchestrations. “ ‘I don’t know the chord changes,’ he’d say, but Gerry would correct him, ‘You know the changes, you just don’t know their names.’ ”

To begin with, there’s the very matter of being able to play the trumpet at all. This is surely the most demanding of instruments—there are no garage brass bands—and properly improvising a jazz trumpet solo takes considerably more training than learning how to walk a tightrope. Yet Baker’s fans preferred to see him as an untutored philosopher. To a certain degree, this was in accord with Baker’s own manipulation of his image and sound; the way he played and the way he lived were embodiments of pure passion. “I play every set as if it were the final one,” he once said. “I don’t have too much time left, and it’s important to show the musicians I’m playing with—more than anybody else—that I give everything I’ve got in me.”

Chesney Henry Baker was born in the Oklahoma Dust Bowl on the eve of the Depression (in fact, shortly after the Wall Street crash), on December 23, 1929. At the start of the war, his family relocated to Glendale, California, where his father worked in the Lockheed plant, allowing Baker to grow up in the jazz scene of Los Angeles. His father was a semiprofessional musician, his mom was a classic stage mother who encouraged him to sing, which he did, starting around the age of eleven or twelve. “She’d drag me around to amateur contests that they had in L.A. I had to compete with girls playing accordion or tap-dancing. I never won. Even at that time I was singing the current ballads.” His father (who had played guitar in hillbilly bands back in Oklahoma) was a jazz fan who encouraged him to play the trombone in the manner of his idol, Jack Teagarden. His arms, however, weren’t long enough to reach all the positions, so little Chettie had to settle for the trumpet.

Between the ages of thirteen and sixteen, Baker learned his horn. By 1946, when he reached sixteen, he was playing so well that when he joined the service and was shipped to occupied Berlin, he was proficient enough to join the post band. Upon returning home, Baker, who was still only eighteen, attended El Camino College in Los Angeles courtesy of the GI Bill. He stayed for only two years, which included the only formal musical training he ever had, and then officially flunked. (The lack of compositional training partially explains why, virtually alone among major modern jazzmen, Baker composed next to nothing.)

He reenlisted in 1950, and by now was playing at a level where he could join a more prestigious army orchestra based in San Francisco. He was also by now comfortable enough with his playing to sit in at several local clubs. According to discographer Thorbjorn Sjogren, in the second year of his second hitch (1951–52), Baker was transferred to a post in the middle of the Arizona desert. Since there were no clubs for him to play in after hours there, he contrived to get out of the army on a psychiatric discharge, and he returned to Los Angeles a professional jazz musician.

His first important job upon coming home was with Charlie Parker (he later paid homage to Bird by recording Parker’s intro to “All the Things You Are”). The legendary Bird had apparently run out of trumpet players and was actually holding auditions among West Coast brassmen; after Baker played (a story Baker himself told and which Jim Gavin questions in his recent biography, Deep in a Dream), Parker stopped the audition and hired him on the spot. The gig with Parker’s quintet was brief, but the two were documented playing together in a privately recorded jam session in spring 1952.

However, a few weeks later—in July—Baker began appearing with the group that would make him into a jazz celebrity, the legendary Gerry Mulligan pianoless quartet. Within a short while, the combination of Mulligan (baritone sax), Baker (trumpet), and bass and drums was the hottest new thing in jazz. This was the most striking jazz ensemble almost since the beginning of the music not to use a piano or guitar or other conventional chordal instrument, and its absence seemed to make the interplay between Mulligan’s baritone saxophone and Baker’s trumpet even more intense. As marvelous a soloist as Mulligan was, he was primarily a composer and bandleader, whereas Baker was purely a player and improviser. Even as soloists, they were perfectly balanced. Mulligan was a creature of intellect, a thinking man’s jazz musician, studied and articulate. Baker, by contrast, was nature’s wild child.

The original Mulligan quartet with Baker enjoyed, essentially, one very good year, from July 1952 to June 1953, in which they recorded prolifically, the high point being an inspired series of sessions in which the quartet became a quintet thanks to the addition of the brilliant Lee Konitz. Yet even at the height of the group’s unprecedented success there were signs it wasn’t going to last forever. As archivist James Harrod has established, Baker first recorded with his own quartet as early as the end of 1952; yet when Mulligan was incarcerated for drug use (Baker was later to follow his example), the initial idea was to keep the quartet going with tenor colossus Stan Getz in Mulligan’s place (a fascinating series of live recordings that were finally issued in the late nineties). However, probably even before the Baker-Getz date, the trumpeter had recorded again with his own group, and the Baker quartet with Russ Freeman made its official concert debut in August.

The emergence of the Baker quartet is important to his singing career, because it’s only when Baker began to be featured as the leader of his own groups that he began singing—on records at least. Between October 27, 1953, and July 1956, Baker recorded the essential twenty vocal tracks of his career, all with his original quartet featuring pianist Russ Freeman. If Baker had never opened his mouth again, he still would be regarded as one of the best of all jazz singers.

These vocal cuts, all collected on the early CD Let’s Get Lost: The Best of Chet Baker Sings (released within a year of Baker’s death), have been issued and reissued in various forms and the collection remains the definitive compilation of Baker’s singing. There are a few additional vocal items, including two more World Pacific (now Blue Note) discs, that go up and down in ensemble size. Grey December contains four 1954 tracks of Baker singing with strings, and Embraceable You, a 1957 date not released until 1995, has Baker playing and singing with very spare bass and guitar accompaniment. There are also two exceptional post-Pacific albums of his singing: Chet Baker Sings It Could Happen to You (Riverside, 1958) and Baker’s Holiday: Chet Baker Plays and Sings Billie Holiday (Limelight, 1965).

Baker’s trumpet playing spills over with virtuosity. It’s been pointed out that he doesn’t have the amazing range of Dizzy Gillespie or the raw power of Clifford Brown, but he can improvise deftly on all kinds of chord changes from blues to standards, he can read off a complicated piece of music like the four compositions by Bob Zieff he recorded in 1957, he can hit a million notes in a bar, and he can play a tricky tongue-twister like Russ Freeman’s “Maid in Mexico,” which requires him to zip through one fast run after another in a swinging, Latin tempo. Baker is without question a great modern jazz trumpeter, worthy of being mentioned in the same breath with Miles Davis and Art Farmer.

In contrast, as a singer he seems to have no technique whatsoever, and yet this state of being completely natural is something he had to carefully cultivate. Baker’s singing has also been described as sexually ambiguous; like Jimmy Scott’s, his voice could either be high male or low female, somewhere between tenor and contralto, and there’s never an attempt to sound cocky or masculine. He sounds so passive, so vulnerable—even more so than the young Sinatra; one imagines that women must primarily have wanted to mother him. And it had to have helped that unlike Jimmy Scott, and perhaps even more than Sinatra, he had poster-boy looks. As with Julie London, one wonders if he would have made it in the 78 rpm singles era. Surely those very appealing pictures of Chettie by Bill Claxton on all those big 12″ LP jackets really helped move product. For men, Baker is an object of identification—I listen to these records and part of my brain thinks “If only I could be that talented, that irresistible, that unspeakably cool.” For women, Baker is an object of desire, both romantic and maternal.

Baker is essentially a modern jazz musician: His solos are bebop solos that use bebop harmonies and bebop rhythm, his drummers use the cymbals more than the bass drum. Yet at the same time there’s something fundamentally traditional about him, starting with, as we have seen, the whole idea of the horn-playing leader as singing entertainer, like Satchmo. His repertoire as a singer is fundamentally songs that were at least a decade old—the newest song on Let’s Get Lost is “I’ve Never Been in Love Before,” from the 1950 Guys and Dolls. More important, though Baker and the quartet may be playing bebop time, they’ve kept everything more than danceable.

There’s a funny moment on the group’s 1954 concert at Ann Arbor, Michigan, in which Baker, apparently in answer to a genuine request, informs the crowd, “We don’t play ‘In the Mood.’ ” But what they play is no less appealing to dancers and listeners who may not be hard-core jazz concertgoers. “But Not for Me” is a fast dance, “The Thrill Is Gone” is a slow dance, but there’s nothing here that a clinging couple couldn’t keep time to. “That Old Feeling” and “But Not for Me” even start out with the verses, played instrumentally and in swinging dance time. “But Not for Me,” even more than “My Funny Valentine,” may be the quintessentially perfect Baker vocal record. Starting with the verse in swing time, there’s a pause before he enters singing the chorus. Both the vocal and the trumpet passages restore to the song the comic irony that was originally its birthright. The intentions of Baker and the composers, the Gershwin brothers, are surprisingly in step. George and Ira wrote it as a torch song with a comic under belly; that’s how Ginger Rogers performed it in the original 1930 Girl Crazy, and how underaged impressionist Mitzi Green belted it, doing a wry parody of Bing Crosby, in the only memorable moment in the dreadful 1932 film of that show. By the time Judy Garland sang it in the superior 1943 adaptation, despite Miss Garland’s own verdant wit, “But Not for Me” was primarily a torch song, and even its many funny lines were meant to sound disconsolate.

Yet Baker reinfuses “But Not for Me” with self-deprecating humor. The message of both the playing and singing would seem to be: Even if your heart is breaking, don’t take yourself too seriously. The trumpet solo, while intricate and boppy, is also as relentlessly cheerful as any Pollyanna. The two 16-bar halves of the chorus solo (as opposed to the verse solo that opens the disc) are separated by what could be called a “false modulation,” in which Baker brightens his tone in a way that suggests raising a half-step without actually going there. Pianist Russ Freeman, not just Baker’s accompanist but also his musical director and even co-leader, catches the mood perfectly with Erroll Garner–like ebullience, propelled by Bob Nell’s Shelly Mannely brushwork before Baker reenters right at that precisely perfect part of the beat in the middle of a stop time break for the “out” half-chorus. It’s surely one of the most rewarding ways to spend 180 seconds that I can think of.

The music is not only danceable but lyrical as well. The two aren’t always the same thing—both Count Basie and Bill Evans (who only crossed paths once with Baker, on the 1958 album Chet) represent one but not necessarily the other. In a 1959 interview conducted in Florence, Baker pooh-poohed the nascent strain of modern jazz that was then beginning to be known as hard bop. According to Baker (who would certainly cut some fairly hard music himself in the company of Johnny Griffin and George Coleman), this new stuff “could only be appreciated by a very few people” and he thought that people would continue to like Chet Baker–style music “because it is more lyrical.” In his view, his own music came more directly out of Charlie Parker and the original bop of the forties: “The old bop was profoundly lyrical. And also it was like a fountain springing continuously, an uninterrupted musical flood, easy to follow.”

Baker’s singing is, from the first note, utterly disarming. Yes, you can qualify a word like “disarming”—it may be true that either it is or it isn’t, but some things are more disarming than others, and Baker’s singing is one of them. He seems so devoid of pretense, so direct in his emotion (or sometimes even his lack of emotion), the singing seems so what-he-is. His pared-down technical machinery at times suggests a hip Alfalfa—he of “Our Gang”/“Little Rascals” fame—a little kid from a more innocent time singing grown-up songs, not screeching (like Alfalfa himself) but playing boy crooner, cooing up to the mike and making believe he’s Bing or Frankie. Like a little girl putting on her mother’s formal gown, the precious precociousness of it all is what makes Baker so endearing. He’s not only deep and romantic—or, as on “My Buddy,” swinging—he’s cute, like a puppy or a kitten.

Many consider the initial phase of Baker’s popularity—the years 1952–1957—when he recorded for Pacific, the height of his career. It is perhaps the greatest period of consistently excellent work, particularly when one factors in the material he recorded with Mulligan. The vocals in particular are pristine and perfect in these years, and consistent in quantity and quality. It’s kind of a mystery why Baker recorded so few vocals over the years; out of the two hundred or so albums believed to exist, not more than five or so are primarily vocal. Even when, in his early live recordings, he performs his signature song, “My Funny Valentine,” it’s usually the instrumental arrangement, similar to the way he recorded it with Mulligan, rather than the vocal treatment he had recorded with his own quartet. In the 1960s, various record labels had him record anonymous dreck like Blood, Chet and Tears, and ten years later, label hacks made him do all-star dreck like You Can’t Go Home Again. Both generations of hacks were trying to elicit a “commercial” product from Chet. If they had merely recorded a few inexpensive sessions of him singing and playing standards with a rhythm section, they would have produced masters of genuine commercial worth that would have been bringing back dividends decade after decade.

Baker’s biography in the years following his “discovery” is better laid out in geographical terms: When was he in Europe? When was he in America? Baker toured the United States for the first time with his own group in 1954 with Russ Freeman, and while in Boston he met a brilliant young pianist (a gig documented on Chet Baker, Boston, 1954 on Uptown Records) named Richard Twardzik. It’s Twardzik who accompanies Baker on his first tour of Europe, or rather who starts the journey, because by the time the group finishes what has since become the longest-ever tour of Europe by an American band, the pianist has died of an overdose.

Rather than learning from Twardzik’s example, it’s when the band returns home to the States that Baker starts using heroin himself. At the same time, he forms another very strong working group of his own featuring Phil Urso on tenor and introducing Bobby “Moanin’ ” Timmons on piano, and in addition to recording with that group makes all kinds of interesting dates for Pacific with everything from a trio to a big band to an inspired team-up with Art Pepper and a reunion with Gerry Mulligan. In New York in 1958 and 1959, he makes four outstanding albums for producer Orrin Keepnews and Riverside Records, including one of his best vocal albums, It Should Happen to You. By the time he arrives back in Europe in 1959, he’s a confirmed addict, a fact the Italian authorities can’t ignore. He is detained in an Italian prison from 1960 to 1962. Among other indignities, the guards subject him to repeated requests for “Cherry Pink and Apple Blossom White.”

But despite his run-in with the European penal system, in light of what happened in America, he would have been much better off remaining far away from home in the late sixties. In the States, he is stuck recording jazz-Muzak treatments of contempop hits by the Lovin’ Spoonful, the Beatles, and the Tijuana Brass—not to mention Blood, Chet and Tears. Worst of all, he is the victim of a mob hit—when he neglects to pay for his habit, he isn’t killed but after the crap is beaten out of him, his teeth are scattered all over the Bay Area. It will be four years before Baker, who is not yet forty, gets a set of dentures and begins to play again.

It was Dizzy Gillespie who helped him get his “comeback” gig, at New York’s Half Note Club in July 1973. He spends the next fifteen years working and recording prolifically, mostly in Europe, occasionally in New York, and on one rewarding occasion in Tokyo. “I work for a lot less than most people,” he says, “but then again, I work a lot more.” He sings in many concerts, and plenty of later live recordings have been issued commercially. There’s no shortage of Baker vocals from 1973 to 1988, but there are very few projects that spotlight his singing in a focused way.

While Baker experimented with dozens of new instrumental compositions in these years, he stuck to a considerably smaller repertoire of vocal numbers—lots of “My Funny Valentine” and “But Not for Me.” The major exception to this rule is “Almost Blue,” by rock-pop singer-songwriter Elvis Costello. Costello didn’t write this specifically for Baker, but by the time the trumpeter was finished with it, he might as well have had.

The visually stunning Let’s Get Lost was released shortly after Baker’s death, and did much to serve the cause of those who loved to look at Chet Baker, from the proto-cool hunk of the early fifties to the withered shell of the late eighties, and listen to him sing (even if his image received more attention than his music). That movie brought Baker’s name to countless new lips and afforded further commercial credibility to the cottage industry that issuing Chet Baker records soon became. These were also the early years of the compact disc, and due to these various factors, the recently deceased trumpeter-singer was one of the more prolific recording artists of the late eighties and early nineties.

Baker’s final recording is believed to be My Favorite Songs: The Last Great Concert (a two-CD package from Enja), from Amsterdam, on April 28, 1988. However, although it was taped only two weeks before his death, because so many new Baker discs constantly spill forth from Europe and Japan, one never knows what the “last” concert may turn out to be. (As of 2010, nothing has been released from the final weeks of Baker’s life—between April 28 and May 13—at least according to Tom Lord’s Jazz Discography.) If the “last” part of the title is up for grabs, however, the “great” moniker indisputably applies: Alternating between a twenty-piece jazz big band for up-tempos and blues and a full symphony with strings for the ballads, the album captures some of Baker’s most poignant playing.

Leave it to Baker to climax the concert—and with it, his entire career—not with the loudest or most dramatic moment, but with the most lyrical. On his final vocal on the song that made his initial reputation, “My Funny Valentine,” Baker not only sustains one note (on pitch) for so long it puts the lie to the idea that he had no technique, but exposes so much tenderness and pathos that he couldn’t possibly fail to break the heart of anyone listening.

What exactly happened that morning in Amsterdam, Friday the 13th of May, 1988? Shortly after Baker’s death, Bruce Weber visited that balcony, and in his opinion, it would have been impossible for anyone to have simply fallen off it—even someone stoned (and the autopsy revealed that Baker was—for once—not), and especially someone who was stoned more often than not. Weber also feels that suicide was unlikely: He never detected any suicidal vibe from Baker in all the time they spent together, and his feeling is that if Baker had decided to end his own life, he would have done it in some sort of spectacularly dramatic fashion—something, say, involving a motorcycle. The only explanation, Weber feels, is that some drug dealer, of the same sort that deprived Baker of his teeth twenty years earlier, sent him flying off that balcony—and into the ages—as payment for an uncollected debt. Jim Gavin, in his definitive biography, Deep in a Dream, makes the educated guess that Baker deliberately jumped.

Who knows? Chance is the fool’s name for fate. Black’s white today and day’s night today: that fall, paradoxically, elevated Baker to a whole new level of “lost,” sending him out even further beyond the reach of those guardians of standards and boundaries, both musical and moral, who could never quite entreat Chet Baker to stay, little valentine, stay.

Tony Bennett (born 1926)

Tony Bennett is the Pangloss of pop. The spirit of Dr. Pangloss, that learned pedagogue who taught the title character of Voltaire’s Candide that we are living in “the best of all possible worlds,” pervades Bennett’s outlook on many levels. It is a guiding force, to begin with, in his interpretation of the songs themselves. “Who Can I Turn To?,” lyrics by Leslie Bricusse and music by Anthony Newley, who introduced it in the London musical The Roar of the Greasepaint, the Smell of the Crowd, is a pretty bleak message. As sung by Newley in the show, the title isn’t so much a question and the message is more like “there is no one to whom I can turn.” Set in a roughly ABAB construction, the song doesn’t have one note of optimism until the second half begins, at which point Bennett comes to the words “And maybe tomorrow …” It’s only a brief section, following which the text goes back to dwelling on the darkness.

But this, for Bennett, is by far the most important part of the song; hearing him sing it, you wouldn’t necessarily think it’s cheerful or upbeat—there’s nothing Pollyanna about Bennett—but it’s uplifting. He also makes the song into more of a declarative statement than a question. His message is “I can turn to you.” He manages to find the one major chord in a sea of all minor, and make that the most important part of the piece: “Maybe tomorrow, I’ll find what I’m after.” In Bennett’s music, anything is possible, hope is never lost.

The Panglossian spirit also influences Bennett’s large-scale view of his own life and career. From the beginning, when he first decided to try his luck as a popular singer as a teenager, Bennett has consistently proved that by giving the world the best performances of the best songs, he can touch the hearts of all who listen to him. And through this miraculous process, both the singer and the sung to are elevated. The better we communicate, the better we can understand each other, and the more we pursue excellence in our lives, the better things become. If you know anything about Tony Bennett, you know this: He truly believes in his heart of hearts that Cole Porter and Duke Ellington can save the world.

Bennett continued to put on a happy face even when, in the late seventies, his career underwent a major derailment when he became involved in a disastrous record venture that it took him years to buy his way out of. Fortunately, by the early eighties, partly through the efforts of his son Danny Bennett who took over as his manager at this time, Bennett Senior was back on his feet again. At this point, Tony could have played it safe: He had standing offers to work for as many weeks a year as he wanted in Las Vegas and Atlantic City. But he couldn’t be content to continue preaching to the converted—in other words to go on concentrating on his traditional Tony Bennett market, those middle-aged fans who had been following him since “I Left My Heart in San Francisco” in 1962 or even “Because of You” in 1952. Rather, he wanted to reach the widest possible audience—not just his traditional followers, but their kids. Bennett is like the baby who can fly because he refuses to believe that it’s impossible.

That he even thought he could do so was a strictly Panglossian conceit. Only in the best of all possible worlds would it be possible—after forty-five years of the singer-songwriters, hillbillies, British invaders, hard rockers, metallic rockers, punkers, and disco dancing queens who have dominated popular music for most of Bennett’s life (his breakthrough hit happened only five years before Elvis). The idea that someone who sang the great show tunes of the Eisenhower era and earlier could compete with heavy metal and rap would have previously seemed fodder for one of those rapidly aging comics who opened for Sinatra, somewhere between the jokes about mothers-in-law and impotence.

But people who thought that way didn’t reckon with the power of the Panglossian attitude that suggests that if you present people with the best music, a significant percentage of them will respond to it and flock to it. Some people (even some people who have worked with Bennett) believe in the lowest common denominator mentality, which postulates that no one ever went broke underestimating the taste of the average Joe. Some people are happy thinking that the only kind of culture that the great unwashed American public can accept is crap. But some people ain’t Tony Bennett.

The key difference between Bennett and Pangloss is that the latter is ultimately exposed as a naïf and even a figure of ridicule. Voltaire uses the good doctor to make his point that the world is not a reasonable, rational place. In Bennett’s universe, though, good things happen to good songs. Bennett, too, might seem naive if the world didn’t keep proving him right, or had he not succeeded beyond his wildest dreams, giving him the opportunity to enjoy what Gary Giddins calls “the longest last laugh in history.”

The supremacy of American music, Tony Bennett has repeatedly insisted, has been due to the dominance of two subcultures: black musicians and Jewish songwriters. There is yet a third group, one that he would seem to be deliberately omitting out of modesty. After Sinatra, Bennett is the greatest of the Italian-American popular singers who dominated American vernacular music after the war. The great Italian-American singers, almost exclusively male (unless you count Joni James or Connie Francis), however, are hardly a uniform species. The true forefather of the Italian school was actually Bing Crosby, who recorded albums of Irish, not Italian songs, and some of the greatest practitioners of the Italianate bel canto tradition were African Americans like Johnny Hartman and Billy Eckstine.

For all of its importance, music was hardly the only Italian tradition to impact upon Tony Bennett: There was also the Catholic Church. When we talk about the religious influence on American music, we’re almost always referring to the stream of African American spirituals into gospel, blues, jazz, and eventually mainstream pop, or we’re talking about composers like Duke Ellington, Mary Lou Williams, Dave Brubeck, or Leonard Bernstein who write music for church performance. For most of the twentieth century, many of the great black singers—from Dinah Washington and Sarah Vaughan on—evolved their styles out of the gospel and spiritual tradition. It stands to reason that Tony Bennett’s music could also be, to a degree, shaped by his own religious experience.

Tony Bennett is the Sultan of Strain; where Crosby and Sinatra advocated a smooth, invisible vocal technique, Bennett, more like Sarah Vaughan, makes his breathing apparatus part of the act. Specifically, he takes the sound of himself straining, holding a note, almost extending to the point where it becomes a moan, and makes that beautiful. One obvious explanation for this approach is the impact on him of African American influences and the blues tradition (as well as the gospel tradition). But it also seems as if Bennett’s straining and moaning are part of his own religious experience, out of the chanting practiced in the Catholic Mass.

Another one of the key features of his music is his penchant for big endings. This is one element that keenly distinguishes him from Frank Sinatra, who preferred to climax most songs about 80 percent of the way through, with maybe two or three lines to go, and then end softly and subtly. Bennett likes to go out with a big, boffo ending. This is partly the influence of Judy Garland, a singer who meant as much to him as anyone. But when one listens to him doing the ending of “How Do You Keep the Music Playing,” you hear it all at once, the unbelievably big ending, with Bennett straining and belting for what seems like an eternity. It’s not merely that he makes straining and belting sound beautiful, which indeed he does, but it’s part of his way of achieving a catharsis with his audience. In a traditionally Catholic way, every time Bennett does one of those amazing, gut-busting ballads, he is, in a sense, symbolically dying and being resurrected. Steve Lawrence once pointed out that every Sinatra performance is like a three-act drama with a beginning, a middle, and an end; each Bennett ballad is more like a passion play, in more than one sense of the term.

It was around the time of Bennett’s seventieth birthday, during the waning months of station WQEW, the last gasp of intelligent pop music in traditional radio broadcasting (in New York, at least), that the question was asked, “What is it that makes Tony Bennett so special?” “Apart from his great voice, his warmth and his swinging style,” the answer came back, “I think what makes Bennett great is the way he simultaneously embodies two distinct kinds of musical cultures. On the one hand, he celebrates the jazz tradition, from Louis Armstrong and Miles Davis on down. Yet at the same time he’s also Mr. Show Business, the living heir to such greats as Judy Garland and Jimmy Durante. There’s no one who lives up to either heritage—let alone both—as wonderfully as Bennett.” Shortly afterward, Danny Bennett was asked the same question—and his answer was remarkably similar: “Tony is the only artist who’s a jazz singer and a pop singer at the same time. You can say that Sinatra is a pop singer with some jazz in him, or that Mel Tormé is a jazz singer with a pop side, but Tony’s the only artist who’s always both pop and jazz.”

How fortunate for us, then, that historical circumstances dovetailed with Bennett’s own ambition to mold him into the perfect representative of both cultures. Tony Bennett was born in the perfect place—Astoria, New York City—and time (August 3, 1926)—to absorb all the right influences. As a child he studied and absorbed the high styles, one by one, of the three great male singers who preceded him: the bravura of Al Jolson, the easy swing of Bing Crosby, the sensitivity of Frank Sinatra. His sister, Mary, told a story about how, at the beginning of the “Sinatrauma” movement, she once made a disparaging comment about the Voice and how Tony, who was about fourteen or fifteen at the time, proceeded to give her a lecture about what made Sinatra so great in specific, technical terms: breath control, timing, and so forth. Barely a teenager, he was already taking the craft of popular and jazz singing very seriously.

In 1944, Bennett reached draft age and went through some of the most disturbing experiences of his life during World War II, first as a foot soldier in the Battle of the Bulge, then as one of the GIs sent to flush Nazi soldiers out of their hiding places as the invading Allies came through, then as part of the forces that liberated the concentration camps. The upshot was that after VE Day, the army allowed him to pursue his musical leanings. In addition to his knowledge of the great pop singers, Bennett also was a child of the big band era. In fact, it wasn’t until he sang with the 314th Infantry Orchestra (a successor to the famous Glenn Miller AAF Orchestra) over the armed forces network in occupied Germany that the young singer enjoyed what could be considered his first extended professional engagement. (Also his first recording: An aircheck survives of the very young Bennett singing “St. James Infirmary Blues” with the 314th Infantry band.)

By a coincidence, most of his early professional engagements involved famous black swing musicians. Before the war, he sang very briefly with altoist Earle Warren, well known for his years with Count Basie, and after the war, he worked as a singing waiter in an Astoria emporium that featured future Ellingtonian Tyree Glenn (vibes and trombone). He spent the immediate postwar period assembling all the elements necessary to launch his professional career and make the bells ring for him. He studied music and theater (courtesy of the GI Bill), auditioning all over the place and singing in any joint that would let him near the microphone.

In these years Bennett began working with his first manager, Ray Muscarella, and his piano-playing alter ego, Tony Tamburello, who became Tony B’s musical director and coach, and reinforced Tony’s own determination to concentrate only on songs of the highest quality. In 1949, Bennett, who for a brief while worked under the name of Joe Bari, made his first recording—for a very short-lived label named Leslie Records. The disc itself, produced by critic George Simon, has not been heard or seen in more than sixty years, although a collector on the West Coast claims to have a copy.Bennett landed his first big break when he had the opportunity to appear with entertainer Pearl Bailey at a nightclub in Greenwich Village. While there, he was heard by comedy superstar Bob Hope, who helped him pick his stage name and invited him to join his troupe for a tour that started at Manhattan’s celebrated Paramount Theatre. His recording career began in earnest when, in 1950, he began singing a rather melodramatic Harry Warren tango (introduced by nonsinging movie star Constance Bennett—coincidentally—in a 1933 picture called Moulin Rouge) titled “Boulevard of Broken Dreams.” The twenty-three-year-old Bennett gave it a belting, dramatic rendition. When a demo of Tony doing the song found its way into the hands of Mitch Miller, the newly appointed head of pop singles for Columbia Records, the bearded producer signed him sight unseen to a year-long contract. In April 1950, Bennett made his first commercial recording for Columbia, with Marty Manning arranging and conducting a more polished reading of “Boulevard of Broken Dreams.”

A year later, however, as Tony tells the story, he still hadn’t made much money for the label, not yet having landed any kind of hit record of consequence, and was in danger of being dropped. Almost randomly, maestro Percy Faith picked “Because of You” for him, a song by Oscar Hammerstein’s uncle, Arthur, better known as a Broadway producer from the early years of the century. “Because of You” was the breakthrough hit that Bennett, Miller, and Columbia had been waiting for, and it at last established Bennett as one of the biggest names in the music business. He was twenty-four years old.

Getting to the top was hardly easy, yet staying there was harder: Even in his first twelve months of glory, Columbia tried to upstage him with two other megablockbusters, “Come on-a My House” by friend Rosemary Clooney and “Cry” by then rival Johnny Ray. Yet for Bennett, “Because of You” was only the beginning: The early fifties saw “Cold, Cold Heart,” “Rags to Riches,” “Stranger in Paradise,” and other chart hits. Today, he doesn’t like the sound of his voice on his early records, and beyond a few hits hasn’t approved any of his fifties singles for rerelease. Which is a shame, because although the early singles are not a patch on what he would achieve from the mid- to late fifties onward, the great albums and the mature hits, they are important documents of the beginnings of a great American artist, and they deserve to be heard.

Even as Bennett was racking up hit after hit, he was never completely at ease in the role of pop star. Teenage girls were putting his picture under their pillows and swooning over him as they had with Sinatra a decade earlier. But, like Sinatra, Bennett wanted to be something more. He found himself frequently at odds with his producer, Mitch Miller, who had specific ideas as to the kind of songs the singer should be recording, whereas Tony had his own plans. Miller had a proven track record with songs that many considered novelties and gimmicks, while Bennett insisted on singing material that meant something to him: first-class show tunes, songs by quality composers. He wasn’t going to waste his breath on anything but the best. Occasionally, Miller would get his way and twist Bennett’s arm until he agreed to do a goofy novelty (among them two sticky-sweet pieces, the quasi-R&B “Cinnamon Sinner” and Ervin Drake’s mockalypso “Shoo-Gah”). However, Bennett gives credit to Miller for bringing him “Rags to Riches” (by future Broadway princes Richard Adler and Jerry Ross) and “Cold, Cold Heart” (the first time a country song became a mainstream hit). Bennett acknowledges that Miller was right about these, but what matters to him is not that they were hits, but that they were great songs. “We were always fencing,” he said. “I always had the sword out.”

Another area where Bennett and Miller were “always fencing” was on the subject of albums. Back then, the producer felt that albums by pop singers were a waste of time; they were strictly something for classical artists, and not enough people in the country actually owned long-playing phonographs to make them worthwhile. By the start of the 12″ LP era, in 1954, Columbia lagged behind the competition in this regard; Capitol Records was releasing albums by Sinatra and Nat Cole, and Bennett wanted to catch up. He also intended to use the album format to expand beyond pop into the realm of jazz singing. The result was the 1954 Cloud 7, which was both his first original album and his first foray into small-group jazz settings. Cloud 7 is the earliest recording of Tony, other than one or two of the better early hits, that the singer professes to actually like, and it was finally reissued on CD in 2004.

By the late fifties, Bennett was concentrating on albums, almost all of which had a jazz bias. The Beat of My Heart (1957), for instance, was notable as the only instance in which a major pop (and increasingly jazz) singer such as Bennett recorded an album based on percussion and emphasized the different approaches to swinging rhythm, as varied as Candido and Art Blakey. Beat of My Heart was also Bennett’s first notable collaboration with British-born modern jazz pianist Ralph Sharon, who would serve as his musical director for most of his career. Over the course of their first stretch together (1957 to 1965), Bennett would make two other classic albums that focused on Sharon’s keyboard work, Tony Sings for Two (recorded 1959, released 1961), a superlative collection of duets, and When Lights Are Low (1964), an even better pairing of him with his regular working trio led by Sharon. (Bennett and Sharon recorded a number of extra tracks for both albums, and some of the trio leftovers were used on the LP A Time for Love. These albums scream for a definitive CD reissue.)

Most of the full orchestra albums also have a definite jazz angle: Tony (1956), which I like even better than Cloud 7, gathered first-rate standard songs with charts by such luminaries of jazz orchestration as Neal Hefti, Marion Evans, and Gil Evans. On the surface, Hometown, My Town (1959) was a concept album of songs meant to reflect the glory and splendor of New York, even though only a couple (“Penthouse Serenade” and Gordon Jenkins’s “Skyscraper Blues”) were songs that specifically referred to New York. Yet Hometown was also a decidedly experimental package, centered on extra-long tracks and extra-lavish accompaniments from an extra-large orchestra (thirty years earlier it would have been called “symphonic jazz”). It was superbly arranged by Ralph Burns, who performed the same chore equally well on the more conventionally jazzy My Heart Sings (1961), another sublimely swinging set of standards with big band.

Then, too, there are Bennett’s two albums with Count Basie, the Count’s first full-length collaborations with a headlining vocalist: In Person! With Count Basie (1958) and Bennett-Basie: Strike Up the Band (1959), both largely arranged by Sharon and Marion Evans. The first was originally intended as a double whammy, not only combining Bennett with Basie, but capturing the singer for the first time in front of a live audience. According to Bennett, Columbia taped him and the band in mono at the Latin Casino, Philadelphia, but producer Al Hamm decided he wanted a stereo album, so he rerecorded the tracks in the Columbia studio with a small crowd applauding and cheering. The tracks have been released both with and without the crowd noises, but it’s an exceptional package either way, climaxing in Sharon’s marvelously up-tempo orchestration of “Lullaby of Broadway,” with its famous vamp.

The second Basie album is perhaps even better. Mitch Miller, who still ran the show at Columbia Pop, was opposed to the enterprise, mainly because Basie was under contract to Roulette and the deal meant that the second Bennett-Basie had to be on Roulette. Yet the Basie influence is a key component of Bennett’s musical makeup, manifesting itself in his flawless sense of dynamics. No one, not even Sinatra, has made greater use of the dramatic possibilities inherent in loud and soft: how he can do a whole number exceedingly sweetly, sotto voce, or use his soft voice for most of a song, and then Pow! Bam! Zonk! Some of his best concert specialties of the last twenty years have been based purely on dynamic expression, like “A Foggy Day” and “Speak Low.” If you’ve ever heard the famous Basie dynamics in action, as on Billy Byers’s arrangement of “All of Me,” you’ll know where Bennett gets his capacity for whispers and shouts.

Not all of Bennett’s early albums were jazz projects: Tony Bennett Sings a String of Harold Arlen (1960) is a lush, semi-symphonic songbook built around Broadway’s jazziest composer with arranger Abe “Glenn” Osser. There also were three pop albums with Frank DeVol using a rather insistent choral background: Long Ago and Far Away (1958), Alone Together (1960), and To My Wonderful One (also 1960). The last includes one of Tony’s own favorite performances, his version of “September Song.” The three DeVol albums are not the most exciting of his career, but they’re consistent—which is more than can be said of many of his albums of the sixties.

Like Sinatra, Bennett has spent his career battling what has traditionally been perceived as the ephemeral nature—the planned obsolescence—of pop music. In the early fifties, it seemed for a brief while that he would be bypassed by Johnny Ray, before Bennett had that remarkable string of megahits from 1951 to 1954. In the late fifties, he had to worry about another Johnny-come-lately on Columbia, namely Mathis, who took most of the singles play away from him while he concentrated on classic albums. In the early sixties, the chief competition was no longer other traditional pop singers of his approximate generation, even though the dreaded Andy Williams was moving vinyl in quantities that were positively obscene. By now, Bennett and his generation were worried that the kiddie pop culture would start to overtake them as the record industry was beginning to have less and less use for traditional concepts like quality and durability.

It was then, with the barbarians about to cross the moat and ransack the castle, that Bennett fought back with his strongest suit yet: another, completely unanticipated, stream of boffo hit singles, delivered as a sort of eleventh-hour reprieve to stay the execution of quality pop. “The Best Is Yet to Come,” originally written for Sinatra but by far the most successful of the many songs Bennett has sung by his close friend Cy Coleman; “I Wanna Be Around,” a title and premise concocted by an amateur tunesmith from Ohio and fleshed out into pop song greatness by Johnny Mercer; two French imports, “The Good Life,” a chanson delivered to Tony by song plugger Duke Niles, who found himself on Tony’s A-list for the rest of his life, and “Watch What Happens,” based on changes similar to “Take the A Train,” and which cemented a solid relationship between Bennett and Michel Legrand, and later Allan and Marilyn Bergman; two West End–to–Broadway imports, “Who Can I Turn To” and “If I Ruled the World,” both with lyrics by Leslie Bricusse. The latter two exemplified Bennett’s long tradition of making hits of show tunes before the shows had even opened, from “Stranger in Paradise” (Kismet) to “Once Upon a Time” (All American), and “Love Look Away” (Flower Drum Song). In all, Bennett’s was the first voice the world heard singing approximately fifty Broadway ballads that eventually became hits and standards.

Bennett’s early career as a pop star climaxed in 1962, almost a decade after the naysayers would have left him for washed up, with “I Left My Heart in San Francisco.” This was one of the biggest hits of the Kennedy era, an early Grammy winner and probably the best-known performance of his sixty years in the music business. Ralph Sharon years before had actually stashed “San Francisco” in a clothing drawer underneath some shirts when he and Bennett were about to perform in the City by the Bay, and decided on the spur of the moment to take the tune with him. It got a favorable reaction in that town when Bennett and Sharon performed it, and the singer convinced Columbia to let him record the song, arguing that it had great possibilities as a regional, West Coast hit—at the very least. Both he and Columbia were completely unprepared for the runaway success of the single.

Right when “San Francisco” was at the top of the charts, Bennett became the first major male pop singer to do an entire evening at Carnegie Hall. The results were then issued as a two-LP set and eventually expanded to a very full two-CD package (released on the thirty-fifth anniversary in 1997). It’s one of the most captivating two hours of music ever recorded, and a potent document of what Bennett’s live appearances were like then. (As a concert performance, it was an anomaly: For another ten years his primary venues were large nightclubs like the Copa, the Waldorf-Astoria, and the various Vegas rooms. He would make the transition to formal concert halls beginning in the seventies.) Tony Bennett at Carnegie Hall—The Complete Concert climaxes with a spectacular showpiece, “De Glory Road,” originally sung by Metropolitan Opera baritone Lawrence Tibbett and fashioned as a show-off piece for a virtuoso voice (such as Tibbett, Paul Robeson, or Bennett) out of elements of traditional Negro spirituals.

Thus Bennett was flying high in the mid-sixties. His mass-pop status was assured by all of his hits, but especially by “San Francisco.” It became one of those songs that everybody knows, part of the collective consciousness, and audiences are just as likely to knock themselves out applauding for it (even though, unlike 99 percent of pop singles, it starts with an out-of-tempo verse) in Singapore, Moscow, or Florence, or even Brooklyn. Respect for Bennett as a serious artist was also accumulating, thanks both to the Carnegie concert and to a widely repeated pronouncement by Frank Sinatra. When the Chairman said that Bennett was the best singer around, nobody disagreed.

Yet there were dark clouds on the horizon. His first marriage was ending unpleasantly, and, culturally, inmates were now running the asylum. By this time, the tables had turned somewhat; ten years earlier, Bennett had to practically force Columbia to let him do a full-length album. By now, the corporation was releasing two or three Tony Bennett LPs a year. Paradoxically, however, where the pre–“San Francisco” albums were artfully crafted (even the compilations, like Mr. Broadway, had a deliberate theme to them), the mid- and late sixties albums were increasingly unfocused. Almost every year brought a new volume of Tony Bennett’s Greatest Hits, and even Yesterday I Heard the Rain, I Gotta Be Me, and For Once in My Life seemed somewhat randomly programmed, with various arrangers and conductors. Make no mistake, these are all terrific albums of wonderful songs, brilliantly sung and arranged, and that was already nothing to take for granted. But there’s little rhyme or reason to most of his late sixties LPs; they don’t lodge themselves in the memory as well as the great Sinatra concept albums or most of Bennett’s earlier long-playing projects.

There were occasional coherent concept albums still, including two of his most beautiful: The Movie Song Album (1965), his last major project for fifteen years with Ralph Sharon, in which a gathering of the most distinguished composers in Hollywood—most notably Johnny Mandel—conducted Bennett in their own themes, and Snowfall: The Tony Bennett Christmas Album, his first meeting with Robert Farnon, the British “guv’nor” of “light music” (which compared to most pop is, indeed, pretty heavy). He also continued to craft outstanding collections of superior songs, in which he explores various moods with a single musical director, such as Who Can I Turn To? with George Siravo, Tony Makes It Happen with Marion Evans, and Something with Peter Matz.

By 1970, Bennett was competing at Columbia Records with Andy Williams and Johnny Mathis, who were, with Clive Davis’s encouragement, making what was called middle-of-the-road or easy listening music, which wasn’t all that different from the unobtrusive sounds that the Muzak corporation was already piping into supermarkets and elevators. A steady diet of Williams and Mathis could lead rock listeners and young people in general to regard all pre-rock pop as Muzak.

But if there’s one thing that Bennett could never be, it was middle-of-the-road. Rock ’n’ roll was supposed to be the music of rebellion, but the real rebels of American music were Artie Shaw, Frank Sinatra, and Tony Bennett, who continually bucked the status quo of the recording industry and stood up for what they believed in. Rather than capitulate, Bennett continually fought off the attempts by Clive Davis and the rest of the company’s upper brass to transform him into an easy listening jukebox. With Mitch Miller, Bennett “always had the sword out”; with Davis, it was more like a bazooka.

The parting in 1971, after twenty years, between Bennett and Columbia Records was not, as is widely believed, the company’s idea. Columbia, on the verge of ousting Davis, wanted him to stay. They still wanted him to record jukeboxy pop hits, but one way or another they wanted him on the label. Bennett elected to leave of his own accord after his contract expired. However, he ended his relationship with the label—for the time being—with two exceptionally beautiful albums, both recorded in London with Robert Farnon: the studio Tony Bennett with Love and the live Get Happy, done with the Royal Philharmonic Orchestra at Albert Hall. For the next seven years or so he went on making records, first for MGM (the label formerly known as Verve) and producer (later turned politician) Mike Curb, then for his own boutique label, Improv Records. His work in the immediate post-Columbia period was of an extremely high caliber: In terms of his own vocals, he sounded better than ever—after twenty-five years at the top he had refined and polished his singing to an incredibly fine point. He also had the benefit of an extremely gifted musical director named Torrie Zito. Zito wrote hundreds of charts for Bennett at this time, most of which, unfortunately, were never documented in any form.

His orchestral albums from the seventies, from Columbia, MGM, and Improv, are generally overlooked. As it turns out, he did some of his very best work in this period, including first-rate albums with arrangers Farnon (The Good Things in Life, 1972), Don Costa (Listen Easy, 1973, marred only by the pretentious and overlong “Tell Her It’s Snowing”), and Zito (Life Is Beautiful, 1975). The last, quite possibly the best of the bunch, is highlighted by an excellent title tune from habitual songwriter Fred Astaire, then Bennett’s Hollywood neighbor (Tony lived in La La Land briefly in the mid-seventies, as a result of his disastrous second marriage, and the only thing he liked about being there was getting to spend time with Astaire). There’s also an exquisite vocal version of the Ellington piano solo “Reflections.”

The Improv period also signified the first occasion in over a decade on which Bennett had the opportunity to record with small groups. His two-LP (single-CD) Rodgers and Hart Songbook started life as a special concert at Lincoln Center. Beyond being notable as only Tony’s second songbook package, this 1973 recording presented him in the most unusual setting of his career, a quartet of cornet, bass, and two guitars, led by Ruby Braff.

Bennett’s other major small ensemble project of the era also resulted in two albums, his 1976 and 1977 meetings with Bill Evans. At the time, most of the world still regarded Bennett as a chart-topping pop singer with little connection to jazz—never mind those albums with Count Basie and many concerts with Duke Ellington. Evans was one of the supreme piano masters of modern jazz, a music that’s supposed to be intellectual and, in Evans’s case especially, introspective. Bennett is essentially an outwardly driven artist, the kind who would embrace the entire audience in his arms if he could; “gregarious” is one of his favorite terms of praise for people and it perfectly describes the singer himself. Evans, by further contrast, was so inwardly directed that our most famous mental image of the pianist has him bending his head into the keyboard as he plays, as if he wants to catch every single sound emanating from the instrument; it almost seems as if he has forgotten the audience—not true, by the way—and has created a personal dialogue strictly between himself and the piano.

How to bridge this gap? Not surprisingly, Bennett and Evans find a common ground in their mutual love for the Great American Songbook and the jazz tradition, yet there’s no attempt by Bennett to sound more “jazzy” than he does usually (he sounds considerably more swingingly jazzy—as the term usually is understood to mean—on Beat of My Heart, Tony Makes It Happen, the Basie albums, etc.). What one might not expect is that Bennett and Evans are further united by their mutual roots in the classical tradition: Bennett is a Verdi aria, Evans is a Chopin nocturne, yet they are fellow travelers on a long road of endless lyricism. I don’t advise it, but if you were to pin Tony to the wall and make him name his favorite album (“San Francisco” would still reign as his favorite single), the two Evans albums The Tony Bennett/Bill Evans Album (1976) and Together Again (1977) would probably be his answer, and most of his fans would agree.

It was a fitting way for Bennett to climax the “classic” period of his career, although the major disappointment of said career is that it had to be ended at all. Bennett was never singing better than in his fifties, as surviving videos and concert tapes (none of which have been legally issued) testify, yet he barely entered a studio for that entire decade. He had other things on his mind in these years: He entered into a second messy divorce, his record company went bankrupt, and his career management was, to put it mildly, inadequate. He was working hard and continuing to earn top dollar playing the major rooms all over the world, but there was no one minding the store. In the early eighties, Bennett moved back to New York around the time that two people reentered his life and helped him get back on track: pianist Ralph Sharon, who climbed back on the piano bench as his musical director, and his son Danny Bennett as his manager.

From the beginning of their professional relationship, the Bennetts were very tightly focused on one goal: Tony wanted to bring the best music that he knew—the music that he had been singing all his life, the music of Gershwin and Basie, of Bobby Hackett and Cy Coleman—to the greatest number of people. The two Bennetts achieved this by gradually making Tony seem hip to the twentysomething and thirtysomething audience. He appeared on the MTV Music Video Award shows (in the company of the Red Hot Chili Peppers); he would do sets at alternative rock (a term that seems something of a misnomer) concerts; he appeared on The Simpsons, the David Letterman show, and every other TV series he could where Generation X, as it had recently been dubbed, was watching.

Yet he would have been unable to do any of this had his recordings not been gradually upgrading his profile. By 1985, the Bennetts had engineered a reunion with Columbia Records—a wise choice, considering that’s where the bulk of his catalogue resided—and his first album in nearly a decade was the much anticipated The Art of Excellence, released in 1986. This was a pivotal recording, an outstanding collection of both swingers and ballads, not to mention those patented Tony Bennett medium tempos (like “City of the Angels,” another Astaire original), and the seductive “What Are You Afraid Of?” Excellence is the album that was worth the wait, the one that made us fall in love with Tony Bennett all over again.

Bennett’s albums over the last twenty-five-plus years have also been artful and excellent. Rather than exhaust my already overtaxed vocabulary of superlatives, let me just say that there’s not a project from this period that’s less than excellent. There are some I don’t play as often as others, like his Irving Berlin centennial homage, Bennett/Berlin (1987), although the premise of both Dexter Gordon and Dizzy Gillespie guesting on a Bennett session is irresistible. Others I listen to so often that they’ve practically spent more hours in my CD player than on my shelves, like the 1989 Astoria: Portrait of the Artist, which weaves fourteen great songs into a de facto autobiography, much like friend Rosemary Clooney’s later similar series of self-reflective albums on Concord; the 1998 The Playground, his only collection of children’s songs; and 1999’s Hot and Cool: Bennett Sings Ellington. The Berlin and Ellington sets represent his only composer-driven packages of the modern era; most of the other sets are tributes to various performers: Sinatra (Perfectly Frank, 1992), Astaire (Steppin’ Out, 1993), Holiday (Bennett on Holiday, 1997), Armstrong (A Wonderful World, 2002), and the overall species of female singers (Here’s to the Ladies, 1996).

Hot and Cool: Bennett Sings Ellington is my favorite Bennett record at least since Astoria—maybe since Excellence. Back in 1960, Bennett gave the semiclassical treatment to Tin Pan Alley’s jazziest resident, Harold Arlen, and forty years later, he takes the works of jazz’s leading composer and puts them into an unfamiliar context, a string orchestra (charts by Jorge Calandrelli, who has supplied most of Bennett’s string writing since Excellence). Half of the album is done with a jazz big band, marking the last time Bennett would collaborate with Ralph Burns, who died two years later. “Do Nothin’ Till You Hear from Me” is a minor miracle. Both of the two major Ellington–Bob Russell songs, “Don’t Get Around Much Anymore” and “Do Nothin’,” tend to be done as bright, upbeat bouncers, yet if you listen to the lyrics, they’re actually quite morose. Bennett is one of the few who address the undercurrent of melancholy in “Do Nothin’,” yet at the same time he turns it into a positive message. He’s telling the object of his love, “You will never ‘hear’ any bad news from me because I will always love you.”

The album that got the most attention, however, was Bennett’s first live-in-concert project since 1971. As the singer was getting more and more attention at alternative rock concerts, his two albums of the early nineties, Perfectly Frank and Steppin’ Out, were so successful that the whole music industry was taking notice. Pop singers of the pre-rock era weren’t supposed to sell that many records to so many young people, especially if they sang only quality music and refused to cheapen their principles. Attention from MTV resulted in a Tony Bennett music video on “Steppin’ Out with My Baby,” written by Irving Berlin for Astaire in the 1948 Easter Parade and which Bennett used to honor both men. The video was so well received that MTV invited him to do an entry in its Unplugged series, a show normally reserved for superstar rock acts. Bennett’s appearance, and the resultant album, were to be the most successful event in his entire career. Within a short while, the CD Tony Bennett MTV Unplugged had sold nearly a million copies and earned the Grammy for Best Album—not just best traditional pop album, a category that he generally won in the face of competition with Rosemary Clooney, but overall album of the year, the category that Michael Jackson, Bruce Springsteen, and Madonna competed in.

Around the same time, colleague and inspiration Frank Sinatra was attracting attention in the twilight of his career for his Duets albums, which can charitably be described as rehashes of his greatest hits with kiddie pop stars stitched in—many of whose fifteen minutes of fame seemed to be over even before the albums were released. What’s remarkable about the Bennett MTV project isn’t merely that Tony Bennett sold a million albums and won the big Grammy, but that he did it merely by being himself, by coming out with his trio—no additives—and singing the same songs he was singing every show for three or four nights a week, about forty-five or so weeks a year.

As it happens, two contemporary pop stars, k.d. lang, who sang beautifully, and Elvis Costello, who did not, joined Bennett on the MTV album, but these duets were merely the icing, not the cake itself. Bennett’s 2001 Playin’ with My Friends: Bennett Sings the Blues is a duet project, but one also done with considerably more class than the Chairman’s comparable albums. Unlike Sinatra Duets and Duets II, Bennett’s album is distinguished by three factors: one, that these are songs new to his career and not remakes of old hits; two, that these are real duets, with both performers in the studio at the same time; three, while I can’t say that all the somewhat contemporary singer-songwriter types who share the mike with Bennett are to my personal liking, I do feel that all of them have earned the right to sing the blues with him—there are no embarrassments like Sinatra and Bono.

The best track on the album is one that he continues to perform as a solo on the road, “New York State of Mind” (I don’t know about you, but I don’t miss Billy Joel at all). Although Bennett hasn’t actually landed any chart hit singles in the digital era, songs like “How Do You Keep the Music Playing” (Excellence) and “When Do the Bells Ring for Me” (Astoria) have become the equivalent of modernday hit singles for him: the crowds cheer madly when he sings them, just as they do for “San Francisco” and “I Wanna Be Around.” “New York State of Mind” shows every sign of becoming the latest of these—when he sings it, especially in the aftermath of 9/11, audiences react as though they are hearing a Tony Bennett classic. And, in fact, they are.

I mentioned Bennett’s hiatus from recording from 1978 to 1985 as one of the major disappointments of his career. There’s one other artistic catastrophe that’s worth addressing here: only half a dozen of Bennett’s classic albums of the fifties and sixties are in print on compact disc. As an artist, Bennett is in a class with Sinatra and Ella Fitzgerald—or something very near it—and like them, he deserves to have most if not all of his catalogue made available, even if briefly, in the CD era. I know it may be too much to expect Bennett himself to sanction the release of a complete recordings package—as has been done for the Columbia output of Sinatra, Clooney, and Doris Day. There are singles from the Mitch Miller era that he never wants to hear again. But though I don’t care for “In the Middle of an Island” any more than he does, in this case I disagree with the artist himself in his decision to suppress large chunks of his own catalogue. The very few missteps he made should be heard if only because of the way they illuminate the great records that constitute the vast majority of his output.

Regardless of what one thinks of the early singles, it’s a crime that one can’t acquire definitive CD editions of such masterpieces as When Lights Are Low, Tony, Tony Makes It Happen, Cloud 7, Long Ago and Far Away, Hometown, My Town, Life Is Beautiful, For Once in My Life, I’ve Gotta Be Me, A Time for Love, My Heart Sings.… The list goes on for days, and Sony is also sitting on two amazing, unissued live albums by Bennett from 1964 (Las Vegas) and 1968 (Los Angeles) that demand immediate release.

Shortly after the death of Frank Sinatra, in 1998, Bennett was invited to help Rosemary Clooney celebrate her seventieth birthday at Rockefeller Center’s Rainbow and Stars. She introduced him with the traditional English line regarding the succession of the monarchy: “The king is dead, long live the king.” In 2002, with the deaths of Peggy Lee and then Clooney herself, Bennett’s position as the last of the great singers of his era—or indeed, any era—is, alas further secured.

Andy Bey (born 1939)

A couple gets into the habit of spending one evening every week in Chinatown. Increasingly, they find themselves drawn into an exotic and, implicitly, erotic netherworld. The more time they spend down there, the more their belief system starts to change: The familiar starts to become strange and surreal to them, while what once seemed bizarre and far-out starts to look like normal. Within a short time, they grow gradually less sure of what they think they know.

That’s the rough “plot,” as it were, of “Tuesdays in Chinatown,” a song that was the most prominent number in the repertory of the jazz singer Andy Bey in the first few years of the new century, a period that was probably the most productive of his entire long career. It was also the title song of one of his strongest albums (released late 2001). I heard him sing it a lot in 2001 and 2002, at shows at both the Kaplan Penthouse as part of Jazz at Lincoln Center’s “Singers over Manhattan” series and the Blue Note.

Yet it’s also a description of Bey’s music: in the way he takes a song everybody knows and completely retools it via harmonic redecoration and elaborately conceived vocal effects. After listening to Bey’s treatments of chestnuts like “You’d Be So Nice to Come Home To” and “Pick Yourself Up,” even such old friends as Cole Porter and Jerome Kern start to seem like strangers in a half-remembered dream. The day of the week and the geographical location of the couple’s descent into delirium are the only thing that Bey is specific about: Otherwise, he keeps everything vague and ambiguous. We don’t know exactly what happens to them, if their worlds are rocked by sex, opium, or egg foo yong.

Maybe it had something to do with the Clinton era. Three of the major jazz vocal stars of the nineties were not newcomers but rediscoveries: Bey, Shirley Horn, and Jimmy Scott (the artist formerly known as “Little”). Bey, who was brought into the spotlight shortly before he turned sixty in 1999, was the youngest of the triad. They all have this thing about time: Each was willing to take every second it took to sing a love song in the most effective way—even if it meant dragging out “Someone to Watch over Me” for nearly ten minutes of just voice and piano. Likewise, they were willing to wait until they were ready for Social Security before being appreciated by the jazz world at large. (David Ritz’s biography of Jimmy Scott is appropriately titled Faith in Time.)

In addition to his elastic, Monkish sense of time, Bey’s greatest strength is his remarkable range: As a young pianist, he learned early on that one can go all the way from deep, sonorous notes in the bass to tinkly high notes in the treble, and it was only a minor leap to the conclusion that he could do the same with his voice. Not surprisingly, both Fats Waller and Sarah Vaughan, Bey’s two major predecessors as explorers of the high-to-low vocal connection, were also accomplished keyboardists. Bey can challenge Billy Eckstine one minute, crooning in a deep basso profundo, and the next intrude into the airspace of Pha Terrell or Stevie Wonder, yelping in a high falsetto. He’s like all of the Ink Spots at once, contrasting Bill Kenny’s stratospheric tenor with the Hoppy Jones talking bass, and bridging the difference in yet a third voice, a comfortable baritone, and employing an attractive rapid vibrato in all three.

If today Bey is a one-man vocal trio, it’s partly because he started as a member of a three-person trio—one that fit the classic description of three people singing with a single voice. Born in Newark in 1939, Bey began his professional life as a child prodigy on the rhythm and blues circuit, playing piano and singing on the same bills as such legends as Dinah Washington and Louis Jordan by the time he was twelve. In 1956, he and his sisters Salome and Geraldine formed a vocal trio, billed as “Andy and the Bey Sisters,” which toured the world nonstop over the next three years (like Jerry Lewis, they were especially beloved in France, where they first recorded) and made three albums. Both that first French session (as yet only issued on an EP), and the first album, an unreissued RCA LP, seem to have fallen off the face of the earth.

However, both of the group’s other two recordings are handily available on a single CD, Andy Bey and the Bey Sisters on Prestige, which documents the combination of snappy rhythms and deep, gospel-style harmony—not to mention eclectic song choices (from Horace Silver to Anthony Newley)—that made them perhaps the best jazz vocal group since Lambert, Hendricks & Ross. Throughout, their sound is deeply rooted in African American religious music, in the churchy timbre of their voices, as well as the wide spacings between the three singers—unlike the Andrews Sisters, there’s a lot of air in there. This is evident when they’re singing three separate lines, as in much of “Sister Sadie,” or even when they’re comparatively closer to one another in something more like conventional harmony, as on “A Taste of Honey.”

Eventually, Salome and Geraldine retired to start their own families back in Chicago, and Bey went out as a solo attraction, accompanying himself on the piano. Like Shirley Horn, he managed to attract the attention of a lot of jazz-and-song cognoscenti without getting anywhere near the big time. His first solo album, the 1974 Experience and Judgment, is a fusion-and-world-music-influenced mistake, considered a disaster even by his fans. Apart from guest appearances here and there, most notably with Gary Bartz and Silver, he didn’t get another album until 1991’s As Time Goes By, a live set from Zagreb distributed pretty much only in the Balkan states.

Bey finally began to record regularly in 1995, and his most important work consists of five albums recorded between then and 2003. Blues, Ballads & Bey (Evidence) is exclusively voice and piano, and Shades of Bey (Evidence) employs a small ensemble (including longtime collaborator Gary Bartz on alto and a string quartet). The 2001 Chinatown (N2K) again ups the instrumental ante (Andy?) with a fuller ensemble that varies from track to track. The most recent performance is American Song (Savoy) from 2003. In 1997, Bey taped a live set at Birdland with the rhythm section of the Bill Charlap Trio—bassist Peter Washington and drummer Kenny Washington—titled It Ain’t Necessarily So and released (on 12th St Records) ten years later.

Shades of Bey opens with Dori Caymmi’s “Like a Lover” intoned by Bey at his bass-baritone best, which he improves by removing almost every trace of Brazilian rhythm, using only Paul Meyers’s guitar for accompaniment. He heads for the bass-ment again with “Dark Shadows,” his homage to Charlie Parker and Earl Coleman. Bey makes the song sound like a predecessor to such later, better known soul ballads as “Since I Fell for You” and “Please Send Me Somebody to Love”—one wishes he would tackle Ernie Andrews’s “Soothe Me” and Cecil Gant’s “I Wonder, I Wonder.” There are two Billy Strayhorn items, “Star Crossed Lovers” and “Blood Count,” and in general, his sensitive rendition does more than anyone else’s (with the possible exception of the younger, more aggressive Allan Harris) to make the case for singing both of these instrumentals as popular songs. Supported by the strings, he also makes an eloquent case for “River Man,” by the short-lived British folk-pop singer-songwriter Nick Drake.

On Shades of Bey, Bey’s singing is considerably enhanced by the guitar, the strings, and the solos and obbligatos of Bartz—one of the best saxists of our time. The joy of Ballads, Blues & Bey is the absolute purity of Bey’s voice and piano. It starts with his six-minute “Someone to Watch over Me,” followed by a masterful, achingly slow eight-minute version of “So Nice to Come Home To.” Unlike Shades, almost all of Ballads, Blues & Bey is overfamiliar songs from the basic jazz singer’s repertoire (there’s more Ellington-Strayhorn: “Day Dream,” “I Let a Song Go Out of My Heart,” “In a Sentimental Mood”—a song not performed often enough by singers—and “I’m Just a Lucky So and So”). He intones “Willow Weep for Me” with considerable authority, which is understandable since he’s been singing about that weeping willow for almost forty years. “Willow” is the first track of the first Bey Sisters album, and when he sings it without Salome and Geraldine, he now uses his high voice to simulate the willow’s wailing and gnashing of teeth.

The 2001 Tuesdays in Chinatown includes, in addition to the gnomic title track, the finest version of Milton Nascimento’s haunting “Bridges” (jazz writer Gene Lees’s best lyric) since Tony Bennett. The lyric’s stated ambition, to build “a bridge made out of love,” seems congruous with the nature of Bey’s music, in which he has bridged the sounds of jazz, soul, scat, theater music, bossa nova, and his characteristic anguish-filled super-slow ballads. Only Bey could take “In a Mist” by jazz Gatsby Bix Beiderbecke and make it sound, in a haunting rendition, more like something written thirty years later by Billy Strayhorn.

Though it sometimes seems as if it takes Bey forever to get through a song (his whole set encompasses only six tunes and an encore), his show literally flies by. At the Blue Note, in 2002, the crowd had probably come to see the young headliner Jane Monheit, who was on the other half of the bill (I’d rather look at her myself, now that you mention it), but Bey made them his own with his first tune alone, “You’d Be So Nice to Come Home To.” At the club, he sang it with only minor support from bass and drums; on the album it’s no less effective by Bey completely solo. He punctuates the whole piece with a percussive, catchy riff, playing in one tempo while singing in another. He intones “breeze on high” in an Arthur Prysock pedal note and “sang a lullaby” in a Cleanhead Vinson squeak; then the second time he sings the chorus through, he completely reverses the trajectory. After an expert piano solo, he sings the chorus again, in yet a third way.

In fact, the only time you’re aware of in a Bey performance is the time between his all-too-infrequent appearances in New York (he continues to perform despite being diagnosed HIV-positive). Otherwise, Andy Bey plays and sings like he’s got all the time in the world.

Connee Boswell and the Boswell Sisters
Martha (1905–1958)
Connie (later Connee) (1907–1976)
Vet (Helvetia) (1911–1988)

Gary Giddins recently described the Boswell Sisters as jazz’s answer to the Brontë sisters. Like Anne, Charlotte, and Emily, Connie, Vet, and Martha were strikingly original thinkers whose work has little or no precedent. Like the Brontës, the Boswells created a literary language all their own. Like the Brontës, the Boswells permanently influenced the course of their art form—American music rather than English literature. And like the Brontës, the Boswells’ career was short (none of the Brontës lived to reach forty; the Boswell trio broke up around the time the oldest sister turned thirty) and their output was frustratingly small. Yet neither of these mediums, the jazz vocal group and the novel, was ever quite the same after these sister acts got through with them.

When we talk about the Boswell Sisters having a language all their own, we mean that both literally and figuratively. The Boswells created their own nonsensical musical vocabulary. Boswellese was essentially a variation on the concept of pig latin that utilized a combination of “G” and “L” sounds, and the insertion of such phrases as “oggle,” “iggle,” and “eggle.” Researcher David McCain, who has spent a lot of his life tracking down the Boswells (making himself the Boswell of the Boswells), once transcribed, with the help of Vet Boswell herself, one of the Boswells’ scatlike exercises in gibberish.

The song—“That’s Love,” written by Buddy DeSylva and Lew Brown (words) and Ray Henderson (music) for George White’s Scandals of 1931—opens with the line “When a bull looks at a cow,” which the trio sings as follows: “Wheggle-den a buggle-dull looks at a coggle-dow.” The start of the second A section is “When two cats upon a fence,” which comes out of the Boswell hopper as “When two caggle-dats upoggle-don a feggle-dence.”

The iggle-diggle folderol was, however, hardly one of their more important musical innovations (for that matter, neither was their propensity for changing lyrics to something that makes less sense than the original, most notably on “42nd Street”), and it’s safe to say that after the trio broke up, no one ever iggle-diggled again. Yet their more strictly musical innovations were a major influence on jazz vocal groups from that point on, from their slightly younger colleagues the Mills Brothers to their successors the Andrews Sisters and all kinds of swing era threesomes, foursomes, and fivesomes, like the Modernaires, the Pied Pipers, and many others.

The Boswells developed a new sound that was startlingly fresh. With the exception of Duke Ellington, no other jazz or pop music arrangers of the prewar era, especially the pre-swing era, so thoroughly recomposed the music they interpreted. Generally the major occasion when a band completely transformed a piece of music into something unrecognizable and new was when they were “swinging a classic.” But by and large, when one band did a new song it didn’t sound all that radically different from all the other dance band versions of said song.

When a pop song like Harry Warren’s “Rose of the Rio Grande” enters the Ellington universe, it still retains its original outlines, but these outlines are filled in with a startling array of tonal colors. The Boswells gave Warren the same treatment when they addressed his 1932 movie musical anthem “42nd Street.” The melody has little in common with that sung by Dick Powell in the picture, the rhythmic emphasis is in entirely different places, different phrases are set out and isolated, melodic lines that one expects to go up will go down instead, there are stops and starts where you least expect them. For the most part, you can only comfortably recognize the song by listening to the lyrics, although “42nd Street” represents a case where the sisters played around with those as well. “Where the underworld can meet the elite” becomes “Where the whole world meets success and defeat.” (I don’t know where those words came from, but I do know when I first heard this rendition on a scratchy 78, it sounded as if they were singing “Where the whole world meets excepting the feet.” It was more charmingly self-referential when they changed “Jelly roll blues” to “Heebie jeebies blues” in “Darktown Strutters Ball.”)

Warren and lyricist Al Dubin ended the song with a dramatic cadenza—“Naughty, bawdy,/Gaudy, sporty/Forty-second Street”—which, in the film, Dick Powell takes to the very top of his tenor head tones. Instead of rendering this 6-bar phrase as a traffic-stopping high-note affair, the Boswells reconfigure it for exclusively rhythmic purposes. Where Powell (and his Broadway heirs) shout it out with exclamation points at the end of every adjective, the Boswells retool it by rushing and then waiting (“Naughtybawdy … Gaudysporty, making two words into one each time) as they lay down rhythmic cells that are the quintessence of swing. Some of the more extreme Boswell performances—like “42nd Street”—anticipate the bop era reworkings of classic songs by Charlie Parker and his followers. In fact, Parker’s “Bird of Paradise” is, after its distinctive opening vamp, easier to recognize as “All the Things You Are” than the Boswells’ ”42nd Street” is easy to recognize as “42nd Street.” The Boswells also touch on the process of harmonic substitutions, to the point of taking major chords and making them minor and vice versa.

The Boswells were avant-garde and mainstream at the same time. Unlike, say, Gil Evans, who spent the better part of his career writing orchestrations and leading bands in dusty dives, the Boswells performed these radical recompositions in your better theaters, on top-rated radio shows, and even in movies. It was to be expected that they would occasionally encounter a radio listener who couldn’t make head or tail of what they were doing. Yet by and large, the big radio audience couldn’t get enough of them. They were by far the most popular female group of the Depression era—in fact, the only one to be remembered by subsequent generations.

If little they did sounded like what you would expect from a pop trio of the thirties—the kind that are always re-created in more modern pop representations, like “the lovely Boylan Sisters” in the Broadway musical Annie—there was a corner of the Boswell brain that had much in common with other heavyweight jazz singers of the era, like Ethel Waters, fellow New Orleanian Louis Armstrong, and co-star Bing Crosby. Sometimes instead of overhauling melodies and trashing lyrics, the Boswells merely reinterpreted them with the same degree of soul and swing, retaining the original shape of the tune as published. This aspect of the Boswells’ legacy comes through in the solo passages in the sisters’ sides, normally sung by Connie, and in Connie Boswell’s own solo sides, done at the same time (and for about thirty years afterward). With her sisters, Connie Boswell is something else again, but even without them she’s easily one of the top vocalists of the thirties, in a class with Mildred Bailey and Lee Wiley (as well as Billie Holiday, Maxine Sullivan, and Waters).

One younger singer who appreciated the dichotomy between the two poles—Connie’s solos and the trio as a unit—was Ella Fitzgerald. Late in her life, Connie (who then spelled her name Connee) gave a somewhat self-aggrandizing interview to radio host Rich Conaty in which she claimed that in the early thirties, bandleader Chick Webb was such a Boswell fan that the drummer put the word out that he was looking for a black female chirp who could sound like Connie Boswell. And so: Ella!

Perhaps it’s not a coincidence that Fitzgerald’s own recording rabbi was also the redoubtable Jack Kapp. In spite of the way Kapp’s musical conservativism gradually took hold, he was responsible for the preservation of at least a hundred classics of the jazz vocal group idiom by the trio. The Boswells made a lot of records in a comparatively short time, enough to fill five compact discs, yet one still wishes that, like Ellington, Fitzgerald, or the Mills Brothers, they could have gone on for decades.

The Boswell Sisters were eternally identified with New Orleans, where they grew up at the very moment that the new music from the Crescent City was taking the world by storm. Martha was born in Kansas City in 1905, and Connie two years later in that same town. By 1911, when Vet (her full name was Helvetia, which sounds suspiciously like a font) came along, the family had moved to Birmingham, Alabama. By the time the third baby was three, the family had settled in New Orleans.

The girls were raised not only by their parents but by an aunt and uncle who lived under the same roof—a quartet of adults who were actually a pair of sisters who had married a pair of brothers. The whole family was intensely musical: At the time of World War I, the little girls were playing chamber music in a string trio (Martha, piano; Connie, cello; Vet, violin), but as New Orleans jazz began leaving its imprint on the rest of the world, the threesome became more of a “hotcha” trio (Martha, still piano, but Connie, saxophone, and Vet, banjo). Sadly, the family lost two sons (one in the war), and the middle daughter, Connie, was stricken with polio as a child, and would be confined to a wheelchair for her whole life. Yet by all indications they were a happy and loving family.

Like jazz itself, the sisters’ music was the product of a melting pot of Crescent City influences. The Boswell family, despite the very Anglo name, was primarily Italian, and thus part of the nation’s single largest Italian-American community. In the teens and twenties, there was almost as much good jazz to be heard in the Italian parts of town as there was in the black neighborhoods, and there was frequent intermingling between the two groups. Obviously, the girls’ musical education, as overseen by a German-born professor, was entirely slanted toward the European classics. Like Armstrong and their childhood friend Louis Prima, they grew up surrounded by the diverse musical influences of the city—everything from the funkiest blues imaginable to the opera house (unlike Armstrong, they were actually permitted in there).

The group was open to every kind of influence, race, and religion. “I remember we would park our car outside black churches and listen,” Vet said in 1981. “Mama believed in finding out what other religions were doing. We’d hear some of the most wonderful Gospel. One song I remember which became our lucky song, ‘The Heebie Jeebies,’ we heard outside a black bar.” “We [started singing] at church affairs,” Connie told Conaty. “We sang at everybody’s church.”

And, like Crosby, they were part of the first generation raised with the phonograph. “I had all the solo records made by the various cellists in those days,” said Connie, “and we listened to the Caruso records, we listed to [Amelia] Galli-Curci, the whole gamut in the ’20s. But we also liked jazz music and swing and ragtime. We bought all kinds of records. I had Paul Whiteman, Gene Austin, Nick Lucas, we had the Wolverines [with Bix Beiderbecke] which was a real hot group.” The combination of local and national influences was extremely important, and Connie relates that even as tots they were combining (national) mainstream pop songs with local music traditions, specifically jazz. No less important was the blending of classical techniques they studied at school with the jazz elements they picked up everywhere else. As Connie said, “We would take a jazz number of some kind, something that was real good with a good solid beat. We would slow it down and maybe put the major tune in a minor, and we would make almost a semi-classical number out of it.”

By the early twenties, the chamber music trio that had evolved into a miniature jazz band had become a vocal trio. In 1921, a group called the Brox Sisters appeared on Broadway in Irving Berlin’s Music Box Revue, and helped popularize the format. Connie dated the birth of the Boswell Sisters as a professional act to 1925; there was an unexpected, last-minute opening in the bill at the Orpheum Theatre—the most important vaudeville theater in town—and, as Connie tells it, the sisters had to get permission from their school in order to fill it. (Actually, only Vet would have still been in school, as Martha and Connie would have been twenty and eighteen by then.) The whole town turned out to see them—their school even closed so classmates could attend—not only because they were hometown faves, but because they were a sensation.

Thus by 1925 they were already local legends. Later that year, a mobile unit from the Victor corporation came through New Orleans, and did two sessions with the sisters, resulting in two issued tracks (the remaining three have never been found). The voices sound extremely young and chirpy, a quality that is exacerbated by the acoustic recording technology, but the two sides—“Nights When I’m Lonely” (the trio) and “Cryin’ Blues” (Connie solo, both tunes credited to Martha)—are important as the first documents of the Boswell Sisters. Van and Schenck (who were, with the Happiness Boys, the most famous singing duo of the time, in the classic twenties tradition of tenor and baritone) made them an offer to come on the road with them, which their father refused, but in 1928 he finally agreed to let the girls take an offer to sing in Chicago. They worked at the Grand Riviera in Detroit, and then, like Nat Cole ten years later, joined a fleabag vaudeville troupe that left them broke and stranded on the West Coast. And that was where things started to really happen for the Boswell Sisters.

In Los Angeles they came to the attention of agent Harry Leedy (Connie’s future husband), who helped them build up an increasingly big following via radio. They made their second record on the coast, “Highway to Heaven” and “That’s What I Like About You.” Their voices have lowered to a more sonically pleasing contralto range, and the rhythm is relentlessly snappy-peppy in the manner of the better early thirties West Coast dance bands, like Gus Arnheim or Abe Lyman. In addition to appearing live on the air five times a week, they recorded a series of transcriptions for radio airplay produced by the Continental Broadcasting Company, of which about two dozen titles have survived. (Most of these are on two CDs: The Boswell Sisters, on Take Two, and The Boswell Sisters: Air Shots and Rarities, Retrieval.)

The Los Angeles transcriptions reveal that the sisters’ mature style is almost fully formed—it’s about 75 percent of the way there. “Song of the Dawn” opens with Connie giving this King of Jazz movie tune religious overtones by singing it slowly and soulfully. The other two don’t contribute much until the second chorus, where the trio takes over and makes it more swing than spiritual. Another 1930 title, “When the Little Red Roses Get the Blues for You,” is very close to the mature sound. They were already both speeding up and slowing down on unexpected passages, and playing up the contrast between the two, and also alternating between the three voices and Connie’s solo.

In October 1930, still on the coast, they cut four titles (“My Future Just Passed,” “Heebie Jeebies,” “Gee but I’d Like to Make You Happy,” and “Don’t Tell Him What’s Happened to Me”) for Okeh that amount to the first recordings with the mature, fully developed Boswell Sisters sound. These, and all the threesome’s commercial recordings, are included in The Boswell Sisters Collection, a definitive five-volume series from Jazz Unlimited, Denmark. The Boswell Sisters: That’s How Rhythm Was Born, from Sony Legacy’s Art Deco series, is probably the best American anthology, even though it doesn’t include any of the 1931 MCA-owned material.

The big breakthrough came the next year. When Bing Crosby signed with CBS and became the biggest thing on the air in the fall of 1931, he opened the door for a pantheon of new-style singerentertainers like the Boswell Sisters, the Mills Brothers, and Kate Smith (who seems less modern in retrospect than she did at the time), who followed him to CBS radio (and William Paley), Brunswick Records (and Jack Kapp), and Paramount Pictures. Crosby was close to both the Millses (with whom he worked on records) and the Boswells (with whom he mostly worked on radio). The singer and the sisters would intersect in all three media, on the 1934 Woodbury Soap series, on several all-star Brunswick discs (usually 12″ medleys and concert items), and in the 1932 Paramount musical The Big Broadcast, which represented a feature film debut for all of them.

In most of her interviews—not that there are very many—Connie Boswell tended to overstate her case, not only claiming that the Boswell Sisters were the first great trio (which they were), but that she was the first great solo jazz singer and even that her older sister, Martha, was the first great jazz pianist. Yet George Simon once documented a conversation with Connie in which she was surprisingly levelheaded. “We didn’t sing everything straight, the way other groups did. After the first chorus, we’d start singing the tune a little different. You know, with a beat, the way jazz musicians would.” This is actually a better description of her own solo records, where she sings the first chorus somewhat straight, then throws in playful, jazzy variations after that, in the classic Ethel Waters mold. On the trio sides, the group often starts by throwing the composer’s melody right out the window, and coming in on the very first chorus with what is pretty much a completely original tune. “Louisiana Hayride” opens with a melody that doesn’t even seem remotely related to the Arthur Schwartz–Howard Dietz show tune from Flying Colors. We don’t hear the familiar melody until it trots in instrumentally in the second chorus, an interlude dominated by trombonist Tommy Dorsey and violinist Joe Venuti. In the Boswells’ topsy-turvy universe, singers take all kinds of liberties with the melody and jazz musicians play it comparatively straight.

“Shuffle Off to Buffalo” marks an especially radical treatment: This was a hit song (also from 42nd Street and again by Warren), and even though it was new, the Boswells knew people would realize what the melody was supposed to sound like. Yet listeners were apparently delighted when the Boswells supercharged the song and completely recomposed the tune. Contrary to Connie’s description, the first chorus here is a total recasting of the musical material—poor Harry Warren wouldn’t even know it. Here the second chorus comes closer to the familiar tune. It starts with the verse, heard in dance tempo (not rubato), and then comes a solo chorus by Connie, which stays closer to the movie melody. Yet for the third chorus, they take off in blasting swing time.

Other numbers find the Boswells introducing melodic interludes from way out in left field. After the first chorus of “Old Yazoo,” the sisters diverge into something completely different, an interlude not even hinted at in the original song (at least not in the song as recorded by Fred Waring’s Pennsylvanians). They introduce a succession of regulation 12-bar blues choruses in which Connie sings the main line (“My Aunt Matty, she told me not to go”) and the others answer back the resolution (“Now she’s listening on the radio”).

“Mood Indigo” also contains a “bonus” extra 12-bar blues passage, instead of the standard second strain as written by Duke Ellington (“always get that mood indigo”). Connie sings her own blues (“Blues all on my mind,/Blues all around my head”), followed by a solo from Tommy Dorsey that illustrates his influence on Ellington trombonist Lawrence Brown. There’s at least one instance where the sisters so completely retool a song that Kapp felt obliged to change the title of the tune. Neil Moret and Jo Trent’s “Swanee Woman” was released by the group on Brunswick as “ ‘Swanee Mammy’—Boswell Sisters version of ‘Swanee Woman.’ ”

At around the time of their breakthrough, newspaper columnists wrote about an alleged feud between the Boswells and “portly warbler” Kate Smith (who, it was said, weighed as much as the three girls put together). Supposedly, Smith and the Boswells were vying to be thought of as the number-one songsters of the Sunny South. Smith, who was at the time billed as “The Songbird of the South and Her Swanee Music,” was actually born in Greenville, Virginia (in 1907, the same year as Connie), and raised in Washington, D.C., which, in the opinion of some, didn’t earn her the right to bill herself as a Southern songbird. (Turkey is more like it, said some.) The Boswells’ Southern credentials were doubted by no one. It seems like a rather trivial pursuit, and indeed it was, but at the time, at the height of the Great Depression, nostalgic songs of home were among the most popular of pop music genres, and songs about the South were big business—as Frank Trumbauer told Hoagy Carmichael (as quoted by Richard Sudhalter), “No one ever went broke writing songs about the South.” In the 1935 Fox musical Every Night at Eight, Alice Faye, Frances Langford, and Patsy Kelly play the Swanee Sisters, a singing trio who become a hit on the radio in obvious homage to the Boswells.

No one ever went broke singing about the South either. In a 1954 article in the British Melody Maker, Martha Boswell claimed that she picked the sisters’ songs by means of astrology. “Martha has an uncanny ability to pick hit tunes,” her husband, George Lloyd, reported. “In her system, she is helped by dreams and the stars.” For Kapp, who probably actually picked most of the girls’ songs, it was much simpler mainly to give the Dixie born-and-bred trio whatever new mammy and Swanee songs crossed his doorstep that day. For Kapp and the Boswells, as I’ve mentioned earlier, such songs were bread-and-butter. This was the greatest era of the American songbook, but you won’t find much in the way of Gershwin, Porter, or Kern in their output—the only major standard from a Broadway show in their repertory was the previously mentioned “Louisiana Hayride,” chosen more for its Louisiana relevance than its Broadway status. Yet I’d rather hear the Boswells do semi-forgettable songs about their paradise back home in the antebellum South than, in fact, almost any other singers doing Rodgers and Hart.

Perhaps Kapp sought to counterbalance their musical progressivism by assigning them songs with socially conservative, even backward content. A song like “That’s How Rhythm Was Born” has the lassies shouting “Yowsah, yowsah” as if in some supremely hip minstrel show. In “42nd Street,” the voices sound geographically neutral; on “Old Yazoo,” they all sound as if they come from L.A.—Lower Alabama.

“Down on the Delta” suggests the rhythmic trajectory of Duke Ellington’s “Daybreak Express,” starting slowly with Connie singing the melody solo—rather heartfully, though not sentimentally—about how she wants to be down on the bayou (rhyming “bayou” with “friends that I knew”) and how she misses the times her mammy used to spank her for playing in the muddy waters. The thing kicks into tempo after a transitional passage led by Tommy Dorsey, and the two sisters come in. After another half-chorus with the sisters, Connie sings a fast solo, followed by a still faster passage by the trio, with a rocking, steady locomotive rhythm that suggests the Daybreak Express plowing down the Yazoo delta where the Southern meets the Dog. Through tempo and rhythm, they render the text and its rather dated preoccupations completely irrelevant.

There seemed to be no limit to the Boswells’ inventiveness. There are plenty of Boswell Sisters records with wordless and scat episodes, and others, like “There’ll Be Some Changes Made,” “Why Don’t You Practice What You Preach,” and “If It Ain’t Love,” where they briefly sidestep through instrumental imitations à la the Mills Brothers. They were among the first North American pop stars to employ the newly imported Cuban rhythm known as the rhumba—heard to great effect in “Whad’Ja Do to Me,” Richard Whiting’s “Don’t Let Your Love Go Wrong,” and most noticeably in a remarkable interlude on “The Darktown Strutters Ball”—they sing “I want to be there when the band starts to rhumba!”

The only records on which they sound less than brilliant are those big Kapp productions for which they were recruited for their star power, not for their musical acumen, as on the 12″ super-special-production discs of “Star Dust” (1931) and “Lawd, You Made the Night Too Long” (1932). The first is the sisters’ own fault; as Vet told David McCain, they were interested in writing their own symphony at this time and somehow that was reflected in this grandiose “concert” treatment of the Carmichael classic. The “Star Dust” chart is attributed to Vet, but it’s hard to believe the sisters had anything to do with it. “Lawd, You Made the Night Too Long” is a wasted opportunity on several levels. The threesome sounds generic here, as if they could be any vocal group of the period. If they had been singing it on their own—without benefit of the concert production—they might have been able to make this Tin Pan Alley spiritual sound like the real thing (which is exactly what they do on “The Lonesome Road” and Clarence Williams’s gospelly “Shout Sister Shout”).

On “Lawd,” they don’t get to interact with Crosby, and singing someone else’s chart makes them boring. In fact, Crosby’s solo on “Lawd” is much more lusty and passionate than their own. Yet on a certain level, to have Crosby singing directly with the Boswells would be too much of a muchness; it would be overkill. (Crosby and Connie Boswell singing together, however, would be sheer magic.)

Beginning in 1934, the Boswells—with Kapp’s cooperation and perhaps even at his instigation—launched what might be called a jazz repertory series, in which they thoroughly reimagined a number of standards of the jazz and pop worlds, such as “Alexander’s Ragtime Band,” “The Darktown Strutters Ball,” “Dinah,” “St. Louis Blues,” the folk song “Goin’ Home,” and the pseudo-folk spiritual but genuine jazz classic, “The Lonesome Road.” This was a bit early even for a 78 album, but one wonders if the sisters or Kapp might have had something like this on their minds. These are probably the climax of the sisters’ career. Yet there were still some great tracks ahead of them, particularly in songs from the new films: Top Hat (“Cheek to Cheek,” “Top Hat, White Tie and Tails”), Follow the Fleet (“Let Yourself Go,” “I’m Putting All My Eggs in One Basket”), and Sweet Music (“Fare Thee Well, Annabelle”); collectively, this is some of the trio’s very best music.

In Radioland magazine, December 1934, Connie denies rumors that the threesome was disbanding, and offers proof of this by pointing out that they had just signed a new contract for the trio to co-star with Crosby on the Woodbury Soap program. But a little more than a year later, the split happened. Writing fifteen years ago, I espoused the theory that the sisters broke up because Connie simply wanted to work as a solo act, and so far no one has come up with a better explanation. The sisters themselves attributed their early retirement to their marriages—like Adele Astaire, they got married and they got out of show business. Vet was expecting her first child at the time the group stopped working in the spring of 1936. She had married a Canadian businessman named John Paul Jones, and Martha married one George L. Lloyd, an air force major who sat on Decca’s board of directors.

However, Connie, who married manager Harry Leedy around the same time, went on working—more than ever, in fact. Perhaps the marriages provided the other girls with a convenient excuse to step out of Connie’s way. Five years earlier, the Rhythm Boys, the group that introduced Bing Crosby to the big audience, had split up for what seem like similar reasons. Yet unlike the Rhythm Boys, the Boswell Sisters never atrophied, never jumped the shark. Perhaps that was just it. They didn’t want to become like Clayton, Jackson, and Durante, or, later, the Will Mastin Trio starring Sammy Davis Jr.—one big-hearted superstar sentimentally lugging two useless ex-partners around for no reason other than not wanting to appear callous. The Boswell Sisters exited the stage in the best vaudeville tradition: leaving us wanting more.

Technically, Connie Boswell’s first recorded solo disc was “I’m Gonna Cry” aka “Crying Blues,” recorded in New Orleans in 1925, which actually preceded the first recording by the Boswell Sisters trio by three days. Her solo career—on records—began in earnest in the fall of 1931, a few months after the trio signed to Jack Kapp’s Brunswick label.

It certainly says something about Kapp’s musical acumen that he was the first to record all three of the great female singers of the early thirties—Boswell, Mildred Bailey, and Wiley (and Fitzgerald, soon enough)—and both of the major males as well—Crosby and then Armstrong. Boswell was hardly a newcomer in 1931, but by the end of the year anyone listening would have immediately put her in the front rank with Bailey and Ethel Waters.

As with Bailey and later Wiley, Kapp teamed her with his star studio players, principally the Dorseys and Brunswick’s number-one hot white road band, the Casa Loma Orchestra. English scholar Eric Woodward has compiled a discography that very informatively shows that Connie’s solos were often recorded at the end of trio sessions—not strictly as an afterthought, but clearly the sisters were still the big attraction for most of the pre-1935 period. Yet even though Connie’s features were obviously of secondary importance, it was in these years that she made her most consistently excellent solo recordings. Her solo sides in the Brunswick period place her very nearly on the same level as Crosby and even Armstrong.

No less than with the trio, Connie constantly animates otherwise forgotten material, starting with her very first Brunswick session. The term applies to such early Boswell solos as “I’m All Dressed Up with a Broken Heart” and “What Is It,” the latter written by ex–Rhythm Boy Harry Barris, which Crosby sang on the radio but apparently didn’t like enough to record commercially. She takes some liberties with the written tunes, as on “I’ll Never Have to Dream Again”: Although it was written as a waltz, she smooths it out into an even four in the second chorus. Also as with the sisters, Connie does even better with songs that have a Southern feel, a blues feel (“The River’s Takin’ Care of Me”), a dance feel (“Cariocha”), and upbeat pop items with a two-beat traditional jazz feel, like “Me Minus You.” She described her own voice as “low and foghornish”; it was deep and sultry, highly sensual, no stranger to the blues. In all of these attributes, Boswell was a perfect female counterpart to Bing Crosby. She was the flip side of Mildred Bailey, a petite femme with a deep throaty sound as opposed to a plus-sized gal with teensy girlish pipes. As the famous journalist Ernie Pyle described Boswell, “so much noise out of such a little package.”

(There are a few decent samplers of Boswell’s solo sides; They Can’t Take These Songs Away from Me is a recommended two-CD set on the British Jasmine label that highlights the 1931–46 period, while Moonlight and Roses on ASV is a good single disc. Unfortunately, no CD has supplanted the two best LPs of Boswell solos, The Early Solos 1931–’35 and Under a Blanket of Blue, both on Take Two, which include most of the best Brunswicks. What is desperately needed is a good Mosaic-style complete box, which may not be possible since her catalogue is divided up—no longer between Brunswick and Decca but between Sony and Universal/MCA. My dream package would include all of the sisters’ sides as well as all of Connie’s solos that are owned by both corporations.)

In the late thirties, the Goddamnedest thing happens: The Boswells follow Kapp from Brunswick to Decca in 1935 (around the same time they do a very successful European tour, and record and broadcast, both as a trio and solos, in England and Holland) and in 1936 the trio cuts its last sides. From 1936 to the 1942 ban, Connie’s Decca sides are surprisingly double-jointed: She made semi-hot and semi-swing sides with a fabulous array of guest stars and accompanists, but at the same time, her regular “mainstream” pop sessions become increasingly dull. This was by no means limited to Boswell; many vocal records of the late thirties are not as exciting as we’d like them to be—arrangers and producers had not figured out a way to transmute the energy of the great swing bands into the discs made by the few star singers of the era.

It’s not merely that not every side of the era is a gem—Connie’s just as likely to find a buried treasure (“Stra-Va-Na-Da [The Double Talk Song]” is a very funny parody of “place” songs, whether set in the Sunny South or an island in the West Indies, and “The Clock Song”—“I Wish We Had a Clock That Had No Hands”—is a touching ballad that never made it). But a certain blandness has set in that is not to be found in the early thirties sides, which can be heard not only in Boswell but in the first few seasons of discs by newcomer Dinah Shore, to Crosbyites Buddy Clark and Dick Todd, to Tony Martin and even, on admittedly rare occasion, to the Mighty Crosby himself.

The pop sides Connie made in these years with the brilliant Victor Young are a bit more distinctive. Young directed two of her best ethnic items in 1941, a lightly swinging, wee-bit-o’-schottische treatment of the traditional Irish “The Kerry Dancers” (later a favorite quote reference for Charlie Parker) and the radically un-PC but delightful “The Gay Ranchero”—at once swinging and Latinate. But the bulk of the pop dates were done under the generally generic batons of Harry Sosnik, Ray Sinatra, and an unbilled studio orchestra. On the whole, the vocal discs of the prewar period illustrate how completely Frank Sinatra reinvigorated popular singing just a few years later, not just in his own vocals but in the intensely interesting and supremely supportive orchestrations of collaborator Axel Stordahl. (Boswell later claimed to have helped discover Sinatra; he filled the funeral hall with flowers when she died.)

There seems to be a dichotomy between vocalists who were billed on their discs as singers “with orchestral accompaniment” and those who were billed in the same way as bandleaders, as in “Mildred Bailey and Her Orchestra” or “Billie Holiday and Her Orchestra.” The discs by the singers billed as leaders are never less than scintillating, largely because they keep the jazz and hot solo content very high. At the same time Boswell’s making sleepy sides with Harry Sosnik, she’s also cutting a series of brilliant, hot sessions with the best bands that Decca had to offer. The spirit of the Boswell Sisters is more than alive and well whenever Connie teams with Ben Pollack, Woody Herman, and the Crosby brothers. The Crosbys in particular ignited the best in Connie: She has the same freewheeling, improvisatory energy as on the classic trio sides. Bob Crosby’s big band was full of New Orleanian star soloists who never fail to bring out her competitive spirit, and she was incontestably the best of Bing Crosby’s female duet partners (even though Judy Garland was a challenger). Spokane Records did posterity a major favor in collating an entire LP of their Kraft Music Hall radio duets entitled Bing and Connie. Their rapport is remarkable, even on nonsense like “Rose O’Day” and “The Hut-Sut Song,” a classic slice of Boswell gibberish that they make even more nonsensical via a Chinese menu.

Even though Boswell was the first—and finest—female singer to follow Crosby into the lower registers, Kapp would never succeed in making her into a female equivalent of Crosby. She was too much a jazz gal; she couldn’t animate and personalize jazzless pop with the same charisma. Crosby almost revels in second-rate songs—sometimes I’d rather hear him sing “Poor Old Rover” and “Just a Kid Named Joe” than “Bewitched”—while Boswell is defeated by them.

Boswell peaked during the war, making one of her best and hottest platters for servicemen with an all-star unit billed as Connie Boswell and Her V-Disc Playfellows, of “Shine on Harvest Moon” and “Goodnight Sweetheart”—first chorus straight, second chorus Dixie-style. A made-to-order role model for the disabled, she tirelessly toured army bases and hospitals. By the late forties, when Crosby was hitting his own high point, she had already crested. Unlike Crosby, who kept socking out number-one hits until the very end of the decade, Boswell now came across like your father’s jazz-pop singer. Unlike Crosby, Boswell’s career was not driven by chart records, but by overall, consistent steady selling of her whole catalogue—which did not endear her to the increasingly cutthroat postwar record business.

Yet, like several other artists of her generation, including Crosby and Wiley, Boswell enjoyed a technologically inspired resurgence in the early years of the 12″ LP and hi-fi. She made a 10″ LP for Decca, Singing the Blues with Connee Boswell (not a typo—by this time she had changed the spelling of her Christian name), but her major output from the postwar era consists of four 12-inchers, Connee Boswell and the Original Memphis Five in Hi Fi (RCA), Connee Boswell Sings Irving Berlin (Design), Connee Boswell Sings the Rodgers and Hart Song Folio (also Design), and Connee (Decca) with Sy Oliver. Crosby’s great late fifties albums—particularly Bing with a Beat and Fancy Meeting You Here—represent a new peak for the legendary singer. Boswell’s, by contrast, do not—fine as they are, they seem more like a great old gal (only about fifty) enjoying a final fling, a last hurrah, one more walk around the garden. Boswell’s voice has deepened and darkened, and seems rhythmically stiffer, now that she’s competing with younger-generation jazz-pop femmes like Clooney and Fitzgerald. Still, all four of these albums are worthy ventures, as fine as they can be (the best is the team-up with the Original Memphis Five, even though Boswell only sings on half the tracks); even the songbook albums are hot and jazzy.

For perhaps the last time the other sisters made the news: Martha’s husband was ousted from the board of Decca in 1954 and tried to sue to reclaim his position, telling the press that Martha had made an invaluable contribution to Decca’s fortunes by picking hit songs with her astrologically based method. Yet, Melody Maker reported, “Despite Martha’s metaphysical aid, Connie didn’t come up with a single hit, said [Decca president Milton] Rackmil.” Martha died at the young age of fifty-three four years later. Connee’s husband and manager, Harry Leedy, died on New Year’s Day 1975, a year before what would have been their fortieth anniversary. Connee herself died of cancer at sixty-eight in 1976, and her illness and death were surprisingly big news in the age of disco. Vet lived to experience the Boswell Sisters revival—groups all over the world that re-created their original arrangements and an off-Broadway show, The Heebie Jeebies, before she died at seventy-seven in 1988.

About the cruelest thing one could say about Connee Boswell’s postwar work is that it was superfluous because Boswell herself was no longer the most important beneficiary of the great work she had done in the thirties, both as a member of the threesome and as a solo act. That crown had been passed to her major successor, Ella Fitzgerald. In a sense, the two extremes of the Boswell canon replay themselves in Fitzgerald’s career—her classic scat features (“Air Mail Special,” “Lullaby of Birdland,” “How High the Moon”) represent, to a degree, her extension of the Boswell Sisters influence, whereas her songbook and more pop-oriented projects more directly indicate the influence of Connie’s solos. Fitzgerald was once asked who inflenced her, and she answered, “There was only one singer who influenced me. I tried to sing like her all the time, because everything she did made sense musically, and that singer was Connie Boswell.”

Al Bowlly (1899–1941)

At his short but prolific peak, Al Bowlly was easily the best male band singer of the thirties—not counting Crosby—on the entire international playing field. Across the pond, there were plenty of capable Americans—Chick Bullock, Scrappy Lambert, Smith Ballew, Dick Robertson, and slightly later, Buddy Clark—but not one who had that combination of swing and soul that distinguishes Bowlly.

There’s a Monty Python sketch that always makes me think of Bowlly—a family of upper-class twits is discussing the merits of words that sound warm and “woody” as opposed to cold and “tinny.” Bowlly has a very wood-like sound. He came to maturity in an age when voices were high, tenor-y and often tinny, and generic. Yet his sound was deeper, lower, and completely idiosyncratic—without any kind of identifiable non-American accent, yet certainly not American. There’s a gray quality about it that reminds me at times of both Al Jolson and Jack Teagarden.

Al Bowlly made a treasure trove of high-quality recordings in London in the early thirties, the best being done under the baton of two superb arranger-bandleaders, Ray Noble and Lew Stone. Although he’s underappreciated today, he was one of the finest swinging jazz singers of any era, and like Django Reinhardt, one of the first Europeans to understand the blues. But the basic idiom he worked in was not necessarily a jazz-oriented one, and many of his most outstanding vocals—things like “Hang Out the Stars in Indiana” and “Midnight, the Stars and You”—have little jazz content. (Which may be why he’s underappreciated.) Yet his presence on a danceband disc by Ray Noble, Roy Fox, or Lew Stone is enough to make the difference between good and great.

Like the young Crosby, Bowlly excelled at both ballads and swingers. There’s a 1931 version of “Dinah,” in fact, in which Bowlly sounds more as if he, rather than Nat Gonella, deserves the title of the “British Louis Armstrong.” He also was, like Armstrong and Crosby, a clear predecessor of Sinatra’s Swingin’ Lover style. Since he worked in the dance band idiom, nearly everything he sings is in a foxtrot tempo—he’s rarely if ever permitted the luxury of singing in a slow rubato. Yet he’s one of those rare artists who make this potential liability seem like a virtue. His great strength, in fact, is love songs sung at a semi-fast clip.

He’s learned what Crosby’s learned: that jazzstyle rhythm is the key not only to giving a performance more zest but to personalizing a lyric, to making it sound more spontaneous and believable; he’s proving what Crosby and Armstrong had already proved and what Sinatra would reestablish a decade later—that the human heart is not only an instrument of emotion but of rhythm.

It’s not too much of a stretch to say that in Bowlly’s musical development he reinvented the wheel. He was born in 1899 and raised in South Africa, although both his place and year of birth are sources of controversy: The area has changed names at least once, and is now known as Mutapo, Mozambique. He grew up in Johannesburg, listening to the indigenous music he heard from black mine workers as well as European and perhaps even American entertainers and bands he saw in the variety halls. Is it taking things too far to infer that he might personally have combined these influences in a way that approximated the origins of jazz in the southern United States, or that his keen sense of rhythm derived from these African roots?

Like Perry Como, he worked as a barber until he was able to support himself by playing guitar and singing. He spent the twenties—his twenties—trekking around the globe and performing with a veritable League of Nations of musicians, many of whom were also continually in transit.

In London, he first began attracting attention from the British musical fraternity when he served as guitarist and singer with the Spanish-born, Cambridge-educated Fred Elizalde, whose orchestra at the Savoy Hotel was considered a breakthrough for British jazz, and included such American stars as Adrian Rollini and Chelsea Quealy. It seemed that Bowlly was always surrounded by fellow travelers—Anglo-Americans and American-Anglos. Within a short while, he would collaborate with Roy Fox and Carroll Gibbons, two Americans who spent their careers in England, and Ray Noble, a Briton who eventually became a major American bandleader.

Some of his first sessions, particularly in London, drew on his background. He worked regularly with other South Africans, making tons of sides that are fairly dreary. The notable point about these discs is their multiculti nature. Here was British and American pop performed in Hawaiian style by two South Africans billed under such pseudonyns as the “Honolulu Serenaders” and the “Brooklyn Broadcasters,” including such regional airs as “Just an Old Italian Love Song” and “Love Made a Gypsy Out of Me.” Bowlly also made records of Western hits for the South African market in Afrikaans.

But soon he was working in the mainstream of dance bands for his musical ability rather than his background. Bowlly hit Berlin and then London just at the height of the Jazz Age record boom. He was incredibly busy in Germany, recording mainly with Briggs and Adeler, and even more so in England. As soon as he arrived in London, he was in instant demand as a studio freelance vocalist, and sang with every conceivable subspecies of dance orchestra, which in England as well as in America were divided between studio-only ensembles and regular working bands (hotel-based bands and touring bands).

He quickly became one of the finest of all masters of the vocal refrain; like the younger Helen Forrest, he understood the discipline of saying all that needed to be said in a single-chorus vocal that usually lasted less than a minute, and he could say more in one chorus than most singers could in a whole record. Small wonder record producers utilized him on over a thousand discs.

Like Forrest, who created substantial bodies of work with three of the top leaders of the era (and unlike, say, most of Duke Ellington’s outstanding singers, who worked only with him), Bowlly reached a pinnacle with several different groups. Where Forrest went from Artie Shaw to Benny Goodman to Harry James, Bowlly worked with two major bands, those of Lew Stone and Ray Noble, simultaneously, in the years 1930 to 1934. It was possible for him to sing with two bands at once since one of these played in a prominent nightclub and broadcast in the evenings, and the other existed only in the recording studio and worked only in the afternoons. No one considered this a conflict, even when Bowlly recorded the same titles, like “Brighter Than the Sun” and “I Love You Truly,” with both bands.

Musically, the two bands were more alike than they were different. For starters, they were both led by extraordinarily astute orchestrators and occasional pianists, who had, obviously, identical good taste in band singers. Yet there were differences between the two, which have a lot to do with the traditional perceptions of his work. American fans tend to prefer Bowlly’s work with Noble, which is understandable, since from almost the beginning American RCA regularly issued the Noble-Bowlly sides in the United States. After Noble himself relocated to the States, he continued to build up a following here, and was to all intents and purposes an American bandleader. But British fans and scholars favor Bowlly’s work with Stone, who became an institution of British music.

Bowlly worked with Noble from 1930 to 1935 and with Stone from 1931 to 1934. The Stone association was centered around the Monseigneur Restaurant in Piccadilly Circus, which, despite its name, was apparently more like an American nightclub, since the resident band was a greater attraction than the food. The band was enormously well received, and recorded prolifically—approximately 150 titles under the name of Roy Fox, a star cornetist imported from America. Yet the match between bandleader and management was not a happy one, and lasted only four months. When illness caused Fox to take a protracted sabbatical, the management seized the opportunity to appoint Lew Stone as the new bandleader. The Monseigneur band with Bowlly stayed intact for another two years, until July 1934, when the restaurant was sold and converted to a cinema (as the Euros say). The timing was actually good for Bowlly, who had one more stop to make on his itinerary: He had an offer to appear in the New World with his “other” bandleader, Ray Noble.

The Fox/Stone–Monseigneur recordings add up to an extremely classy batch of wax. For one thing, the quality of the songs is generally well above average, and Bowlly manages to work wonders even with a bizarre number like “Mediterranean Madness,” which rhymes “through your shadows I grope” with “you mesmerize me like dope.” There also are wild production numbers, like the ersatz Polynesian “Mauna Loa,” and “Laughing at the Rain,” which features wind sound effects, and Bowlly actually getting a sound in his voice as if he’s outside, belting in the middle of a thunderstorm.

There are some exceptional ballads with Stone and Fox, or as close to balladry as you could get in foxtrot tempo circa 1931–34, like “Please Handle with Care,” Jerome Kern’s “Lonely Feet,” and the haunting “Riptide.” Yet on the whole it’s the hot titles that really stand out. One of the first entries in the Fox series is a rendition of the future hot standard “Them There Eyes” that doesn’t completely suffer in comparison with the more famous Gus Arnheim–Rhythm Boys–Bing Crosby version of the same tune. Both versions feature their stars as members of trios and as gifted scat singers, but where Crosby is already somewhat cool, Bowlly is red-hot here and full of energy in his scat solo. I actually prefer the Stone-Bowlly version of “My Woman” to Crosby’s; Bing is slow and dramatic, but Al is hot and torchy at the same time—“lusty” is the only word for it.

“Junkman Blues” and “Balloons” are both production numbers built around the cries of street vendors, but while both are insinuatingly catchy, the first is also blazingly hot. “Junkman” is one of several Fox-Stone titles in which Bowlly shares the vocal action with Nat Gonella, the Satchmo of Bow Bells. Bowlly plays a supporting role while Gonella is the star of “Kickin’ the Gong Around,” an audio escapade that literally acts out the Harold Arlen–Cab Calloway specialty as if it were a radio drama. The two of them interact in a way that anticipates Crosby and Armstrong (as well as Armstrong and Teagarden) on “I Got Rhythm,” “Tell Me, Are You from Georgia,” “How’m I Doin’.” He also sings a hot-and-tusty chorus on “Nobody’s Sweetheart” over a trumpet obbligato from Gonella.

The meat of the matter was dance music, and Noble and Bowlly produced well over two hundred sides together in about five years—enough to fill a fourteen-LP box in the early eighties and a nine-CD series today. Considering that the New Mayfair Orchestra was completely anonymous, and that both the Ambrose and Jack Hylton bands had first choice of new songs, Noble’s achievement seems miraculous.

Bowlly and Noble (like the Boswell Sisters and Dean Martin) worked wonders with absurd songs that no one remembers otherwise. The Anglo-American Harry Woods was no Richard Rodgers—although he was called in to write additional songs for the film version of Rodgers and Hart’s West End hit Evergreen—but he wrote two Bowlly-Noble classics that manage to be homey and celestial at the same time. “Hang Out the Stars in Indiana” and “Midnight, the Stars and You” (the latter featured in the Stanley Kubrick horror epic The Shining) both have a heavy camp factor that doesn’t deter Bowlly in the least.

Many of the very best Noble-Bowlly tracks are the work of two composers, both of whom were also pianists, arrangers, and bandleaders—Johnny Green and Noble himself. Green wrote “What Now,” “Not Bad,” “Oceans of Time,” and two of the strongest entries, the aforementioned “Weep No More My Baby” and the equally classic “You’re Mine You.” It’s hard to sing lines like “we’re chained and bound together” and not sound heavy, but Bowlly and Noble keep it simple and flowing, rhythmic and romantic.

Unlike Stone, Noble was a highly successful songwriter, responsible for at least ten fine tunes he recorded with Bowlly that did not survive the period, and four more that can be considered standards: “Goodnight Sweetheart,” “Love Is the Sweetest Thing,” “Love Locked Out,” and “The Very Thought of You.” (Later, in America, he would write several more standards, most notably “I Hadn’t Anyone Till You” and “Cherokee.”) “Goodnight Sweetheart” was an immediate transatlantic hit, recorded by Crosby, among other American stars. But my favorite is “Love Locked Out,” if for nothing more than the way Bowlly illuminates Noble’s rather fanciful lyrics, which anthropomorphize the emotion of love into some kind of vaguely Cupid-like figure who goes around beating his tiny wings on the doors of unsuspecting victims, blessing all those who have the good sense not to lock him out.

The Noble-Bowlly relationship was blessed from the git-go. The Noble-Bowlly ballads are generally in strict foxtrot tempo—no Sinatra-style rubato here, mate!—and yet the ballads with Noble sound more intimate than what anyone else was doing with a dance band. He wasn’t afraid to reduce the band to a single section, a few tightly muted trumpets, an extended trombone solo (“Hiawatha’s Lullaby”), and in general he exploited the superior ability of the HMV engineers to capture a dynamic range unheard of elsewhere in pop.

The short vocal on “Standing on the Corner,” a 1933 song so obscure that it can’t even be described as forgotten, is a thing of rare beauty: Bowlly knows exactly which words to emphasize, which to hold, which to sing louder; but more remarkably, he knows to underplay the lyric. When he does stress a word, it has a powerful effect, particularly as he achieves this emphasis in a characteristically subtle fashion—singing the phrase (“And I’ve got no—body”) just slightly louder, but mainly calling attention to it by dragging the beat just the slightest bit and widening the pause between syllables. He sings some passages staccato, emphasizing the beat; others legato, letting the rhythm flow freely.

This attention to nuance, using rhythm and dynamics to make every word count, reminds us most obviously of Frank Sinatra. In fact, Ray Noble himself later spoke of a long-standing disagreement he had with Bowlly over the singer’s insistence on singing behind the beat for emotional effect; Tommy Dorsey later had exactly the same beef with the young Sinatra. Lew Stone once told interviewer Cliff Harvey, “I used to be very worried about this in the early days. But I soon understood that this was an integral part of Al’s technique—it always came out right and added a fuller dimension to the song.”

As fine as the ballads are, most of the Noble-Bowlly titles that would accompany me to the desert island would be the hot sides. Some of these pieces are purely rhythmic novelties, including one of the earliest, the hot Hawaiian “Makin’ Wickey Wackey Down in Waikiki.” “Shout for Happiness” has Bowlly in a musical dialogue with muted trumpeter Max Goldberg, while the euphoric “You Ought to See Sally on Sunday” has him egging on a baritone sax solo by the excellent British reed virtuoso Freddy Gardner. Bowlly could even syncopate a tango, as on “Goodnight Vienna,” and best of all are those torch songs that he puts over in an unexpectedly red-hot fashion, like the 1932 “Must It End Like This?” The arrangement on the first two (instrumental) choruses is merely peppy, Noble providing in this case an almost passive background over which Bowlly can really go to town, throwing in all sorts of Armstrongian interjections.

This was the height of Crosby’s influence, yet Bowlly digs beyond Bing to the American singer’s own influences, especially Armstrong (also plainly heard on “Hustling and Bustling for Baby,” a performance that can stand comparison with Armstrong’s own version) and Jolson (acknowledged in the cry of “Mammy” that Bowlly apparently ad-libs at the end of “My Hat’s on the Side of My Head”). Bowlly could also get close to the edge of the blues on “Blues in My Heart,” “Seven Years with the Wrong Woman,” and “Who Walks in When I Walk Out?” In all, there are more than enough of the purely jazz titles to fill a disc all by themselves.

Although the years 1931–34 were Bowlly’s pinnacle, this isn’t to imply that the later work was not good. The best titles with Noble and Stone have a magical quality about them, a spell that was broken when Bowlly traveled to New York at the end of 1934. Ray Noble was brought over to form a band for the newly opened Rainbow Room at the top of Rockefeller Center, and another rising arranger-composer-bandleader, Glenn Miller, put it together for him. Noble and Bowlly recorded extensively with the American group in 1935 and 1936; though this was a band filled with present and future stars (starting with Miller himself, and including Bud Freeman, Will Bradley, Johnny Mince, Claude Thornhill, and Sterling Bose), Noble’s Rainbow Room unit had neither the style nor the spirit of the New Mayfair organization. The Rainbow Room band sounds best on purely swing specialties, like Miller’s charts on “St. Louis Blues,” “Chinatown, My Chinatown,” and “Way Down Yonder in New Orleans,” but Noble has apparently lost his knack for turning grade-B tunes (such as “You Opened My Eyes”) into grade-A records. The chief attraction here is Bowlly, and he is actually better served on a series of recordings he made under his own name in New York, accompanied by both Noble and Victor Young’s Decca house band.

Back in the day, they referred to these as “personality” records, where the singer was featured most prominently, as opposed to dance band records where the singer usually only sang one chorus with the band, if that. Bowlly had recorded sporadically as a soloist up to the New York sojourn, but he would do many more solo sessions both in America and afterward.

By now, he regarded London as his permanent home, and when in 1937 Noble relocated once more—this time to Hollywood—Bowlly returned to Mother England. He had a difficult time reestablishing himself in his adopted country, however, especially since he went through a series of vocal problems in that first year back. He continued to guest with the leading British bands of the late Depression and early wartime era, such as Geraldo, Felix Mendelssohn, and Ken “Snakehips” Johnson, the last being a black West Indian who worked with Bowlly on two slices of swinging Shakespeare in the spirit of Maxine Sullivan.

Some of the later solo sides are quite lovely, even though a lot of the time he was saddled with dreary songs (“Romany,” “Somewhere in France with You”). Worse, as was the case with many solo singers in the immediate pre-Sinatra era, such as Dinah Shore, Connie Boswell, and even the Mighty Crosby, the orchestrations on most of his vocal records of the late thirties are fairly formulaic and unimaginative. Yet there are some terrific solo titles from the last few years, especially “South of the Border,” “Marie,” “Bei Mir Bist Du Schoen” (intriguing, quasi-up-tempo treatments of songs that were swing band hits in the United States), “A Man and His Dream” (one of the nicest Crosby movie songs), and “Moon Love” (a Tchaikovsky adaptation). The best is his haunting, melancholy treatment of “Over the Rainbow,” which opens with a paraphrase from the bridge (played on celesta), then goes into the verse, and then the chorus, in which Bowlly finds a completely different meaning from that of the young Judy Garland. Garland sings it like a wide-eyed ingenue, dreaming about the land over the rainbow. Bowlly sings it like the voice of experience, like an old-timer who’s been there and back.

In 1938, Bowlly reunited with ex-boss Lew Stone for approximately two dozen titles that, overall, are the most consistently good of the post-American recordings. A lot of these are heavy on the sentiment (“Little Lady Make Believe,” “The Girl in the Alice Blue Gown,” and especially “Penny Serenade”), while “The Frog on the Water Lily” is rather juvenile and the evocative “Moonlight on the Highway” recaptures the feeling of the pre-1934 discs. The best are a subseries of titles that show that he had everything it took, vocally and rhythmically, to keep up with the best band vocalists of the swing era: “Georgia’s Got a Moon,” “Down and Out Blues,” and the wild scat feature “Mama I Wanna Make Rhythm.” He is positively radiant on two outstanding Jerome Kern–Oscar Hammerstein titles from the film Joy of Living, “You Couldn’t Be Cuter” and “Just Let Me Look at You,” which show that despite career and personal setbacks, he still had lots of great music left in him.

At the end of his life, he teamed with a fellow guitarist and singer named Jimmy Mesene in a duo billed as “The Radio Stars with Their Guitars.” They cut four songs together, all fairly uninspired sides, hardly a fitting conclusion to a spectacular recording career. Bowlly’s last record was Irving Berlin’s love song to Adolf Hitler, “When That Man Is Dead and Gone” in which he looks forward to the day when “Satan with a small mustache/Is asleep beneath the lawn.” (All four titles are reissued at the end of one of the more comprehensive Bowlly CD reissue packages, The Al Bowlly Story, a series of three individual CDs that samples his whole career in England and America from 1928 to 1941, on the British Avid label.)

It’s difficult to imagine what would have happened to Bowlly had he survived the war. The tide of popular entertainment had already turned, if not against him, then at least away from him; with a few exceptions, the dance band era did not lead to a period of superstar pop singers in Britain the way it did in the United States, and he was already going through a rough patch at the time of his death, in April 1941. Bowlly was regarded by his friends as a bit of a naïf, and God only knows what he was doing in his apartment during an air raid; it’s not as if the Londoners hadn’t constructed shelters precisely for such occasions. The bombs fell, and his flat, as they say, was instantly flattened by what the London papers called “the German murder gang.”

Most of Bowlly’s fans over the last seventy years associate him with a very particular time and place—thirties London. His life was much broader than that. His reissues are often packaged as mere nostalgia, an insult never handed to Armstrong but one that the reputations of Crosby and Jolson are only now transcending. Bowlly is simply one of the finest spirits ever captured on record. With his slightly husky timbre that anticipates Tony Bennett as much as it echoes Crosby, he is a genuine, three-dimensional personality that speaks to us across the generations on shellac surfaces that spin at 78 rpm. Journalists at the time tended to use the term “crooner” and “jazz singer” as if they were interchangeable. In later years, this was proven not to be apt, but, in Bowlly’s work, the two roles are one and the same.

Dee Dee Bridgewater (born 1950)

There’s a curious chronology at work in the development of important singers. The cultural holocaust known as the late sixties completely scuttled at least one whole generation, with the result that virtually no notable singer of jazz or standards would make his or her entrance in these years. It might be said that not even one important artist was born in the entire decade of the forties, so crushingly complete was the influence of baby boomer pop.

It’s hard to name even a single world-class jazz diva born between Nancy Wilson (1937) and Dee Dee Bridgewater (1950). However, in recent years it’s becoming increasingly apparent that there is a new gold standard of jazz singers, and that Bridgewater is at its epicenter—along with Cassandra Wilson (born 1955) and Dianne Reeves (1956). (Diana Krall, born 1964, surely deserves honorable mention at this point, but even though she has made significant strides in recent years, both artistically and professionally, and even though her album sales are the biggest of all, she’s not quite yet ready to be placed in the same pantheon as Bridgewater, Wilson, and Reeves, who have been working at it ten to fifteen years longer.)

If Wilson is the most introverted of the three, then Bridgewater is the most extroverted, while Reeves takes the middle ground. As good as Bridgewater sounds on her records, she’s also the one who most needs to be experienced live to be fully appreciated. She depends a great deal on visual presentation—not just the way she looks but the way she moves (undulates would be a better word). In both big concert halls and more intimate nightclub settings, she quickly transcends the barrier between the merely flirtatious and the openly seductive. Not content to overexcite the men in her audience, she seems intent on giving us all heart attacks. She’s not just in your face, she’s practically in your lap. Clearly, she thrives on the interplay and reaction from the crowd, and at least at one point in her career, her willingness to do anything to please the audience led her down some ill-advised paths. (Did someone say “disco”?)

As is also true of Reeves, the very elements that are supposed to make jazz singing obscure and esoteric—scatting and severely rewriting familiar melody lines—are the principal tools that Bridgewater uses to enchant an audience. It’s all about energy, musical as well as erotic. She’s irresistible when the tempo is fast and the chords are quickly changing—more than Wilson or Reeves, she excels at taking the really overdone basic jazz warhorses and subjecting them to the kind of workout that a first-rate jazz tenor saxophonist or pianist would, as on the live “All of Me” and “Just Friends” on her 1990 In Montreux and “Fascinating Rhythm” on Keeping Tradition. She just takes these tunes and runs up and down them with relentless invention, riffing on both the melody and the harmonies, the rhythm, anything she can get her hands on.

One thing Bridgewater rarely does is sing a classic love song in an intimate, open, and vulnerable way. This is actually one of the things she manages somewhat more frequently on record—perhaps it’s easier for her in the isolation of a studio with no audience present. When she appeared at the Iridium around Valentine’s Day 2002, the only time she reduced the tempo was for “Come Sunday,” thereby establishing a mood of reverence rather than romance. She slows down on In Montreux for “A Child Is Born” (in honor of her first major bandleader, Thad Jones) and then for “Strange Fruit,” a pair of songs about birth and death rather than the boy-girl thing. The major romantic number on Tradition is a medley of two Sinatra-associated songs about vulnerability and the frailty of emotions, “I’m a Fool to Want You” and “I Fall in Love Too Easily,” yet here the medley is set up so that one pays more attention to the bright way in which the two tunes are overlaid than to the emotional content. Likewise, on “Stairway to the Stars” (on Live at Yoshi’s) heartfelt expression takes a back seat to a very entertaining routine in which she mimes the sound of a muted trumpet by moaning (I’m guessing) into her hands.

For all her female wiles, Bridgewater’s key strength is a very direct muscular modernism—in other words, hard bop. It’s no surprise that after including several compositions of Horace Silver’s on Tradition and Montreux, she would build an entire album around his music, entitled Love and Peace. Like others from the hard bop movement of the late fifties and early sixties, Bridgewater was essentially a jazz artist with strong ties to blues and gospel, as well as what later became known as soul and funk—not for nothing was the term “soul jazz” generally interchangeable with “hard bop.” In these years, Silver and Ray Charles could have played with each other’s bands and few listening would have noticed the difference, and certainly nobody would have complained. Equally certainly Bridgewater could have served as girl singer with either band (she has, in fact, performed with both of these iconic pianistbandleaders).

She was born Denise Garrett on May 27, 1950, in Memphis, Tennessee, and was precisely the right age to participate in the beginnings of the formal jazz education system. As a burgeoning musical talent growing up in the sixties (a decade in which the music gained few converts), she might somehow have missed jazz altogether had it not been for her father. Professor Garrett was a music teacher and a trumpeter whose pupils included many of the brilliant young men of Memphis who made an important impact on jazz during the hard bop era, including Booker Little, Charles Lloyd, and George Coleman. Dee Dee, as she was nicknamed, was singing professionally in Michigan by the end of the decade, and in 1969 had joined the University of Illinois Big Band in time for a tour of the Soviet Union.

The next year, Garrett married a talented young trumpet player named Cecil Bridgewater (born 1942), and the two of them came to New York to seek their fortunes. Both their careers did indeed take off, even if the marriage only lasted a few years. Between 1972 and 1974, Bridgewater sang with the premier large jazz ensemble of the day, the Thad Jones–Mel Lewis Orchestra, permanently ensconced on Monday nights at New York’s Village Vanguard. She turns up on several of the Jones-Lewis band’s recordings, most notably on “The Great One,” a movement from the 1971 Suite for Pops.

Around the same time, Mrs. Bridgewater toured Japan with the Vanguard Orchestra and, while in Tokyo, recorded her first album, Afro Blue, on the Japanese Trio label. The album featured her husband, Cecil, as well as tenor saxist Ron Bridgewater (no relation, apparently), pianist Roland Hanna, and bassist George Mraz; the set was widely regarded by the jazz community as an auspicious debut. She opens in an unexpected way for a future star singer: The first track, Mongo Santamaria and Oscar Brown Jr.’s “Afro Blue,” starts with a long, meandering intro, an amorphous, directionless blob of sound in which her voice is one of many sonic elements. This particular idea seems rooted to its time and place, yet when she finally starts singing the song, everything works. (She uses a variation on the idea in the intro to “Love for Sale” on the Live at Yoshi’s album.) Unfortunately, Afro Blue has yet to be made available on a domestic CD.

The jazz world had by now accepted Bridgewater as a budding star and, as a result, we were collectively disappointed when she left us. Nobody minded when, in 1974, she joined the cast of Broadway’s The Wiz as Glinda (the part Lena Horne played in the movie), and especially not when she won a Tony Award. But most of her other work over the next ten years or so seemed to involve every kind of music except straight-ahead jazz and standards; instead, she turned out albums of disco, fusion, kiddie pop, and other regrettable distractions.

If there’s one track from this period that’s worthy of our attention, it’s the final cut on her final pop album, from 1989. The album is titled both Victim of Love and Precious Thing in different releases, and the song itself is titled “Till the Next … Somewhere” on various issues, but the important thing is that this is her duet with Ray Charles (who himself was also known under several different names in his career). I would rather they were singing “Let’s Call the Whole Thing Off” or “Two Sleepy People,” but still the two of them have an amazing chemistry. I’m not crazy about the song—whatever you want to call it—but this twosome could make anything sound good.

In the eighties, Bridgewater relocated to Paris and since then has made Europe the center of her operations. She has remarried and raised Franco-American children, and she has also become a hero to jazz lovers across the French-speaking world (as I experienced firsthand when I caught her at the Montreal Jazz Festival in 1997). Equally important, she has been able to put together and work with her own full-time rhythm section. She was gradually coming back to the jazz orbit, although she also enjoyed several further triumphs on the musical theater stage: playing the title role in the London production of Stephen Stahl’s Billie Holiday, a role that earned her a Laurence Olivier Award nomination (though the extroverted Bridgewater doing the dark, mysterious Holiday seems, on the surface at least, not what I would consider a good idea), and starring as Sally Bowles in Cabaret.

By the turn of the nineties, Bridgewater, who was still based in Paris, was at last ready to make a fulltime commitment to jazz. In 1990, she recorded her “comeback” album, In Montreux, announcing the return of the prodigal in one of the most famous jazz festivals in the world. Over the last twenty years, her output has not been huge (the meat of it consists of seven studio albums) but every one of her projects has been a success. One point that’s as unusual as it is commendable is that there has been only one general purpose studio album, the 1993 Keeping Tradition; every other Bridgewater release has been driven by a concept. There are two homages to pantheonic diva foremothers: Dear Ella (1997) and Eleanora Fagan (1915–1959): to Billie [Holiday] with Love from Dee Dee (2010); two songbook projects, one devoted to a comparatively traditional Broadway songwriter (This Is New, a collection of Kurt Weill songs; 2002) and the other to a composer-instrumentalist-bandleader whose music is only rarely sung (Love and Peace: A Tribute to Horace Silver; 1995); and two geographically inspired collections, J’ai Deux Amours (2005) and Red Earth: A Malian Journey (2007). In addition to In Montreux, there is another live album, the Grammy-winning Live At Yoshi’s (1998). Two additional concert performances have been released on DVD: Dee Dee Bridgewater Sings Kurt Weill Live at North Sea Jazz (2004; mostly songs from This Is New) and Live in Antibes and Juan-Les-Pins (2005; mostly songs from J’ai Deux Amours).

Yoshi’s in particular was a powerhouse of a project that not surprisingly garnered the Grammy for 1998, a disc of long improvisations that, like the best of Betty Carter, thoroughly justify their time allotment. Bridgewater’s highly developed sense of humor and playfulness come to the fore here more than anywhere else, especially when she apparently spontaneously scats out “Sex Machine,” and then offers her impression of how Ella Fitzgerald would sing that James Brown hit, as well as the improvisation that precedes the melody and lyrics to “What a Little Moonlight Can Do,” and the way she frames Ray Noble’s “Cherokee” with the dancing infidels theme of Dizzy Gillespie’s “Shaw Nuff.”

If I play Dear Ella less than the other tribute sets it’s because in doing an album of songs associated with Fitzgerald (a swell marketing hook, by the way) she sets herself up most determinedly for a comparison with the First Lady of Song. I feel the same way about Dianne Reeves’s 2001 tribute to Sarah Vaughan, and sometimes I think I enjoy Ann Hampton Calloway’s Fitzgerald tribute album more because AHC sounds less like Ella. It was singularly classy of Bridgewater to recruit and feature two of Fitzgerald’s favorite musical collaborators, pianist Lou Levy (who shines on “Mack the Knife”) and the Great Lady’s bassist and husband, Ray Brown.

Keeping Tradition, the themeless studio album, is also highly enjoyable. Still, none of these projects accurately captures what Bridgewater achieves in person, in a club or concert hall. The two composer-driven packages may well be Bridgewater’s most wholly successful records, because they provide her with another dimension to work with. On most jazz vocal albums, everything is all about the singer; here everything is also about the composer, which gives us a point of reference, something else to think about.

You can’t quite capture her spontaneity and presence, even in a live recording, so the best option is to go the other route—for a carefully prepared program rather than a singer whose greatest achievement may be her illusion of impulsiveness. Since Bridgewater has already proven herself in musical comedy and pop as well as jazz, it’s only natural that she should also use an approach from the world of cabaret. In the cabaret world, artists are often expected to stick to one theme or songwriter for the whole evening; in jazz and related pop, not so much. Just as recordings can’t capture what’s freshest and most vital about a live performance, a live performance shouldn’t try to indulge in a single theme for a whole evening like a record—note that Sinatra never did Only the Lonely in concert, and neither did Ella Fitzgerald do The Rodgers and Hart Songbook. Yet Bridgewater, like a jazz-cabaret hybrid, has done the whole Weill project, This Is New, as her act.

The Silver and Weill packages bring out the very best in her. The Silver set (Love and Peace) for the most part uses the composer’s own lyrics, which, as is also true of the late Benny Carter, probably represent the least of his many talents. Yet this deficiency doesn’t slow Bridgewater down in the least. As with Ivie Anderson singing Ellington or Ethel Merman doing Irving Berlin, the voice sounds tailor-made for the material, perhaps the result of growing up in the same environment as George Coleman and Booker Little.

Throughout, Bridgewater is backed by trumpet and tenor (the French Belmondo brothers, Stephane and Lionel), a sound intended to echo the famous Silver Blue Note–era quintet. The presence of two hard bop keyboard masters, Jimmy Smith and Silver himself, on two tracks each, also lends the album an air of authenticity. Bridgewater is everything that the music of Silver is supposed to be: tight, swinging, and sexy. She told me that she initiated this project after she had come back to jazz after Broadway and pop: She wanted to show off her jazz chops with a catalogue of music that only a 100 percent simonpure jazz singer could do. And she succeeded.

On the other hand, This Is New, though undeniably the work of a superb jazz singer, also calls her theatrical side into play. Kurt Weill was a Germanborn composer of avant-garde classical music who ultimately found his greatest success writing show tunes on Broadway. Bridgewater is an American jazz singer who wandered through show music and kiddie pop before finding her jazz roots again in a foreign land. By now, too, a Bridgewater production was a family affair: her ex-husband did the arrangements, her current husband served as co-producer, and two of her daughters served in the vocal backup group.

Though This Is New draws on Bridgewater’s Broadway background, it’s no less thoroughly a jazz project than Love and Peace. She starts by treating the title song to tropical rhythms, while “Alabama Song” becomes a rowdy blues, one that marches through references to the Jazz Messengers and Benny Golson. “Lost in the Stars,” normally rendered as a kind of musical oratory, is here intoned surprisingly tenderly and personally, while “Bilbao Song” (the first performance that springs to mind by a major jazz diva) juxtaposes flamenco and tango and other Spanish rhythms. Even at ten minutes—not a second of which is wasted—“Bilbao” is so compellingly sung and surreally imagined that one wishes this song would replace Jobim’s over-performed “Waters of March” as the number-one foreign art favored by jazz vocalists.

The last ten years have been especially rewarding for Bridgewater. The four excellent albums she’s released (plus the two live sets on DVD) follow a clear trajectory. The first track and title song of J’ai Deux Amours is Josephine Baker’s theme, known in English as “Two Loves Have I” (thankfully she avoided the original English lyric, “Give Me a Tune”). Like Baker before her, Bridgewater means it: She is equally a product of both America and Europe, and with strong African roots as well. (Somehow “J’ai Trois Amours” doesn’t sound right.) Appropriately, This Is New and J’ai Deux Amours showcase her European side (although the first highlights her Broadway side as well), while Red Earth: A Malian Journey explores her African ancestry, and Eleanora Fagan: To Billie with Love honors a great American forebear.

J’ai Deux Amours consists of familiar French songs (only a few of the eleven tracks are sung even partially in English) that are interpreted in a new way musically, blending accordion, guitar, and other traditional sounds of French pop with state-of-the-art jazz textures. It sounds very contemporary, and, for once, I genuinely intend that as a compliment. On “Ne Me Quitte Pas” she makes Jacques Brel sound musical (practically a first), while in “Dansez Sur Moi” (a.k.a. “Girl Talk”) she proves that Bobby Troup’s infamously chauvinistic lyric sounds better in French, spiced up with fender bass and funk beats. “La Mer (Beyond the Sea)” swings in the original language and in a way that’s totally different from Bobby Darin (or even Kevin Spacey). Oui, oui, madame!

Perhaps it’s not a coincidence that Bridgewater is the only singer I can think of whose name is a scat phrase. I don’t mind hearing Bridgewater sing in languages I don’t know (which is virtually all but one of them); make no mistake, she’s all about the groove rather than the lyric, and she could tell a story in Swedish or Swahili and be completely comprehensible. Red Earth is an album of irresistible grooves; most of the album consists of Bridgewater singing over different implements of percussion (lots of pan-African marimba) and a wide range of beats and time signatures. I knew only a few of the thirteen songs beforehand (this is not the Great American, or even European, Songbook), but the whole set is compelling. Two 1960s jazz standards are here: “Afro Blue,” which is an appropriate opener, and Wayne Shorter’s “Footprints.” Both are reconfigured to sound completely different from any previous version, vocal or instrumental. She supplies a whole new melody to Nina Simone’s “Four Women.” Simone did it as a performance art monologue: Bridgewater sings the piece rather than speaking it, but still makes it dry and understated and highly moving. The most impressive track is the finale, “Compared to What,” which was also the basis for a rather amazing lavishly produced video (viewable at youtube.com). Bridgewater belts out the tongue-twisting, rappish lyrics with incredible passion; this is highly inspired funk, funk with a purpose, funk with a mission. Compared to what? Compared to anything.

After Bridgewater visits Broadway, Berlin, Paris, and Mali, she goes to her roots as a jazz singer from the American South with Eleanora Fagan. She portrayed Billie Holiday onstage throughout Europe in the late eighties, but here she’s not impersonating the legendary diva so much as showing how her music is still relevant in the new century. She proves that her strengths are stronger than anyone else’s and her weaknesses matter less and less. Holiday was the master of almost suicidally despondent love songs, and this is still the weak spot for Bridgewater, but it never stops her: She does “Lady Sings the Blues,” for instance, in a hard-hitting 6/4. This is a defiant and upbeat description of the blues. Bridgewater focuses on the playful and jubilant side of Holiday’s legacy. “Your Mother’s Son-in-Law” is a frisky frolic between voice and bass with Bridgewater and Christian McBride, while “All of Me” and “Miss Brown to You” are also joyful rompers. “God Bless the Child” and “Strange Fruit” are obviously more serious, but since they’re not supposed to be intimate (one person communicating directly to another) Bridgewater is all over them. The cover shows her naked from the shoulders up (except for an emblematic high gloss gardenia), looking like one of Goldfinger’s victims covered in metallic body paint—not to mention that she’s the world’s sexiest sixty-year-old.

The shame of Bridgewater’s career is that even though she started early, she didn’t hit her stride until her fortieth year. The few projects she’s released since then, however, prove that Dee Dee Bridgewater was well worth waiting for.