“There were only two women in his life,” is the way Nellie Monk explained it to me. “Me and Rubie.”1 No one disputes Nellie on this point. Leaving aside Monk’s doting mother, Rubie Richardson was Monk’s first real love, a source of joy and pride and an even greater source of heartache. He named one of his most beautiful ballads, “Ruby, My Dear,” after her—although whether or not he wrote it for her is a source of great intra-family debate.
Beautiful and elegant, possessing smooth light-brown skin, a sparkling smile, shapely legs, and what most men in the 1930s thought of as a heavenly figure (despite a penchant for buttermilk), Rubie was undeniably one of the most desirable young women in San Juan Hill. You could identify Rubie from far away because she liked wearing a white flower in her hair, like Billie Holiday.2 She also ran with one of the most popular cliques in the community. Rubie and her younger sister Linette were members of a social group called the “Brown Snapperettes.” Mavis Swire, an acquaintance of Rubie’s and decidedly not a member of the group, remembered the clique as “all of those girls in the neighborhood with shapely legs, who danced well and who the boys adored! They were the in-group. These were very attractive, very well put together, very sophisticated girls.”3 They were known for organizing socials at the community center, but they also had a reputation for being “a little snobbish.”4
Monk’s nephew, Theolonious, described Rubie as “high yellow [light-skinned]. Her family was ‘up there,’ they were uppity. Rubie was crazy about Thelonious.”5 Sonny’s youngest sister, Skippy, was less charitable; she used to say Rubie was “such a much.” On the other hand, Marion Monk and Rubie had been the best of friends since they were about seven or eight years old. Geraldine Smith described them as “two peas in a pod.” Later, Rubie became godmother to Marion’s son, Alonzo, and all of Thomas and Trotyrine’s children grew quite fond of their “aunt.” Not surprisingly, Marion was responsible for introducing Thelonious and Rubie.6
If anyone detected an air of superiority in Rubie’s behavior, it had more to do with her Caribbean background than her actual class status. Her parents, Ackland and Florence Richardson, were born in the British West Indies, married on the eve of World War I, and immediately joined a small exodus of West Indians to Cuba seeking refuge from the British draft and work in Cuba’s cane fields. Five of their six children were born in Cuba, Rubie being the second, born in 1917, and the eldest of their three daughters. They did not stay long enough to learn the language. In 1922, Ackland decided that the United States offered a brighter future, so he headed north to secure work and housing for his family. Like most Caribbean immigrants who joined the post–World War I exodus, New York City was his destination. Within a year he found a job driving a truck for a plumbing supply company, moved into a tenement apartment at 205 West 60th Street, and sent for his family. His wife, Florence, found work as a laundress.7
Neither Thelonious nor Rubie had expressed any romantic interest in one another prior to his tour with the evangelist’s band. Although they were acquainted through Marion, they ran in completely different circles, in part because she was a grade ahead of Thelonious. However, when he returned, mature and worldly, Rubie began to look at Monk differently. The skinny kid who used to impress the neighborhood girls with his piano playing was now a confident, irresistible, ambitious, and eligible man. Once they came together (around 1937 or 1938), Rubie became a fixture in his world. She accompanied him virtually everywhere—community dances and parties, and the small dives where he worked. Frequently, Marion tagged along. “Oh, man, they could dance,” recalls Alonzo White. “My mother used to tell me her and Rubie used to go out to clubs when my uncle was playing. And in those days if you were a musician you’re playing to an audience who would dance. It was dance music that you played. . . . You were supposed to have some fun; they didn’t come there to listen. They came there to party.”8
Barbara adored Rubie and both of Thelonious’s siblings treated her like family. The same cannot be said about the Richardsons. “Rubie’s parents didn’t like him at all, period,” Geraldine Smith remembers. According to Nellie, Thelonious wasn’t allowed in their house. “They had to meet on the corner.”9 He didn’t make enough money, he was a musician, and he wasn’t of Caribbean descent. Rubie’s parents did not think much of Monk nor of his music, and felt that she was wasting her time waiting for him to make it. Rubie herself seemed skeptical of her boyfriend’s musical path. She often asked him, in a variation of the eternal nagging question asked of all struggling artists, “Why can’t you play music like the Ink Spots?”10 In the usual version, the struggling artist recalls this question much later, when he is wildly popular. Yet those nagging questions often have a grain of truth to their assumptions. Thomas Monk, Jr., recalls that “Uncle Bubba [Thelonious] would come to my father and would say, ‘I want to marry Rubie but I can’t because I ain’t got no money.’ And my father said, ‘Well, money’s not everything. When Rita and I got married I didn’t have a dime. I was broke and scuffling.”11
Despite his reassurances, Thomas was less than confident in his older brother’s ability to marry, settle down, and have children. Trotyrine, in particular, was thoroughly convinced it would never happen. After all, being on the road was an occupational hazard of the professional musician; it was not conducive to family life. So when Trotyrine gave birth to their third child on January 29, 1939, they decided to bestow upon him the vaunted family name of Thelonious. Someone had to continue their father’s legacy. When Trotyrine filled out the birth certificate application, however, her spelling error produced “Theolonious Monk.”12
Monk doted on his new nephew and relished the idea that they sort of shared a name, but he really wanted to marry Rubie. He also wanted to make enough money to move out of his mother’s house and make a living. “I tried to find jobs,” he recalled nearly twenty years later. “I worked all over town. Nonunion jobs, twenty dollars a week, seven nights a week, and then the man might fire you anytime and you never got your money. I’ve been on millions of those kinds of jobs. I’ve been on every kind of job you can think of all over New York. I really found out how to get around this city. Dance halls. Every place.”13 He took whatever jobs he could get—house parties, bar mitzvahs, local dives, even a polka band. According to Monk, these early gigs paid about seventeen dollars a week, and some were absolutely miserable. “There are a lot of things you can’t remember—except the heckles.”14 He once told a friend that he had to back up singers “who sing all kinds of songs and fuck up and blame it on the musicians.”15 He desperately needed a new piano. With help from his ever-supportive mother, he cobbled together enough cash to purchase a very fine, but used, Klein upright piano which became a fixture in his bedroom.16 The only thing left to do was join the union. So in March of 1939, he paid his dues and became an official member of the American Federation of Musicians Local 802.17
Monk joined the union along with Eddie Heywood, Jr., a fellow pianist whom he befriended. Just two years older than Monk, Heywood had been playing professionally since he was fourteen years old. His father, Eddie Heywood, Sr., was an accomplished pianist and singer who backed several jazz and blues artists during the 1920s and 1930s, including such forgotten legends as Sippie Wallace and Butterbeans and Susie. Eddie, Jr., began working with Benny Carter immediately after obtaining his union card, and over the course of the next few years he recorded with Coleman Hawkins and Billie Holiday. He would emerge as a popular ensemble leader in his own right.18
Heywood really encouraged Monk as he navigated the world of professional musicians. Thanks to his father, Heywood had already gotten to know many of the older stride piano players, James P. Johnson, Willie “The Lion” Smith, Luckey Roberts, Clarence Profit, and the incomparable Art Tatum. These pianists used to get together at each other’s homes for friendly jam sessions and to share ideas, and apparently Heywood brought Monk along and introduced him around. The time Monk spent among these elder statesmen and their students was as important, if not more important, to his musical development as the time he later spent with bebop greats. By Monk’s account, he left a lasting impression on several of them, including Eddie Heywood, Jr. As he put it in a 1963 interview, “Every day I listen to pianists who are using my technique. If you don’t know them, I know them very well. Listen to someone like Eddie Heywood, for example.”19
Pianist Billy Taylor first met Thelonious at one of these gatherings in September of 1939. Taylor, just eighteen at the time, had come up from Washington, D.C., to hear Teddy Wilson and Charlie Christian play with Benny Goodman’s band at the World’s Fair in New York.20 Much to Taylor’s disappointment, Wilson had left Goodman to form his own group, but when he tried to catch the Wilson big band at Harlem’s Golden Gate Ballroom, they had the night off. Instead, Taylor wandered into a small club managed by a friend of his father, the pianist Billy Taylor, Sr. He introduced himself, and the manager said, “ ‘Oh yeah! Your father tells me that you play the piano?’ I said yes and he said, ‘You’ll have to come back and play something for me.’ He takes me back there and there’s a trio playing.”21
“I proceeded to play my favorite song, ‘Lullaby in Rhythm,’ and I thought I was really doing something. The piano player kept looking at me funny and I didn’t realize it was Clarence Profit since I’d never seen him before. So here I am, playing his composition on his gig! Once I finished, Profit came up to me and said, ‘Hey kid, that wasn’t bad. I have some friends that would like to hear you play.’ ”22 The pair proceeded to a brownstone on 140th just west of Seventh Avenue. Taylor still did not know that his escort was Clarence Profit, or that the house they were about to enter belonged to the legendary James P. Johnson. “There’s some guys sitting around playing cards. He says, ‘Hey fellas! I have a piano player here!’ They said, ‘Sit down, kid, and play something.’ Now I should have known. [laughs] But I sit down and start playing ‘China Boy’ which was a tune I’d heard Teddy Wilson play. He was on my mind so I was doing my version of him. You know, my left hand was doing this little thing? I got about sixteen bars in when one of these guys comes over and says, ‘Hmmmmm, that’s nice. Let me try a little of that?’ He sits down and, man . . . ! This guy has got a left hand that I didn’t believe! He was just like Waller. Turns out that everybody in the room was a piano player! I mean, these guys sat down one after another and just played! Nobody had to say anything. I just sat there and thought, ‘Oh shit!’ ”23
“Turned out that one of the guys was Monk! It was the first time I ever heard him. But get this! . . . The other guys were Willie ‘The Lion’ Smith, a guy named ‘Gippy,’ and James P. Johnson!” Willie “The Lion” then called Monk over to the piano bench. “Willie ‘The Lion’ was kind of on his case. He said, ‘Play your thing, man.’ And he sat down and played a standard, I believe it could have been ‘Tea for Two.’ He was playing more like Art Tatum then. I think he really responded to the older musicians who told him to do his own thing.”24
Monk told Billy Taylor “that ‘Willie ‘The Lion’ and those guys that had shown him respect had . . . ‘empowered’ him . . . to do his own thing. That he could do it and that his thing is worth doing. It doesn’t sound like Tatum. It doesn’t sound like Willie ‘The Lion.’ It doesn’t sound like anybody but Monk and this is what he wanted to do. He had the confidence. The way that he does those things is the way he wanted to do them.”25
Willie “The Lion” never mentions Thelonious in his memoirs, but he described these evenings memorably: “Sometimes we got carving battles going that would last for four or five hours. Here’s how these bashes worked: the Lion would pound the keys for a mess of choruses and then shout to the next in line, ‘Well, all right, take it from there,’ and each tickler would take his turn, trying to improve on a melody. . . . We would embroider the melodies with our own original ideas and try to develop patterns that had more originality than those played before us. Sometimes it was just a question as to who could think up the most patterns within a given tune. It was pure improvisation.”26 A later generation of bebop pianists would often be accused of one-handedness; their right hands flew along with melodies and improvisations, while their “weak” left hands just plonked chords. To the great stride players that gathered at Johnson’s house and elsewhere, the left hand was just as important as the right. A weak left hand was one of Smith’s pet peeves with the younger bebop piano players. “Today the big problem is that no one wants to work their left hand—modern jazz is full of single-handed piano players. It takes long hours of practice and concentration to perfect a good bass moving with the left hand and it seems as though the younger cats have figured they can reach their destination without paying their dues.”27
Teddy Wilson, though only five years older than Monk but considered a master tickler of the swing generation, had nothing but praise for Thelonious’s piano playing. “Thelonious Monk knew my playing very well, as well as that of Tatum, [Earl] Hines, and [Fats] Waller. He was exceedingly well grounded in the piano players who preceded him, adding his own originality to a very sound foundation.”28 Indeed, it was this very foundation that exposed him to techniques and aesthetic principles that would become essential qualities of his own music. He heard players “bend” notes on the piano, or turn the beat around (the bass note on the one and three might be reversed to two and four, either accidentally or deliberately), or create dissonant harmonies with “splattered notes” and chord clusters. He heard things in those parlor rooms and basement joints that, to modern ears, sounded avant-garde. They loved to disorient listeners, to displace the rhythm by playing in front or behind the beat, to produce surprising sounds that can throw listeners momentarily off track. Monk embraced these elements in his own playing and exaggerated them.29
What Thelonious took from the elders he shared with the young cats. He spent many afternoons jamming with his peers. Besides Denzil Best, Monk hung out with another young trumpeter named Benny Harris. Nicknamed “Little Benny” for his diminutive size, Harris was also younger than Monk and Best by two years, but he had already established a rich, clear tone on his instrument. And like Best, he, too had Caribbean roots. His father, Joe Harris, was a Kuna Indian from the San Blas Islands off the coast of Panama, and his mother, Essie, was a North Carolinian who also claimed Indian heritage. Whatever their ancestry, it is clear that one or both parents were of African descent as well. It’s possible that they both emphasized their Indian heritage because, during the late 1920s and early 1930s, Joe was the live-in superintendent of an all-white building on East 18th Street. The idea that the family was “Indian” and not “Negro” might have made the tenants more comfortable.30 But they didn’t stay there long; they relocated to San Juan Hill where Little Benny became immersed in the musical community. He started out on French horn and Eb mellophone, becoming a member of The New York Daily Mirror’s children’s band at age twelve. At age thirteen he picked up the trumpet and practiced earnestly for two years after school.31
Harris got to know Monk after he returned from his stint with Reverend Graham, in part because they both hung out at the Columbus Hill Community Center. Being younger than Monk, Harris looked up to him: “Monk played the piano, always dressed sharp.”32 Like Monk, Little Benny was only fifteen when he went on the road with a touring band, though they only went as far as Pennsylvania. After he returned, Harris and Monk “played many afternoon parties together at which they not only earned money but filled up on good food, too.”33 In 1937, Harris met trumpeter Dizzy Gillespie and began to adopt his modern harmonic ideas as well as his sound. It was Dizzy who got him his first real gig with the Tiny Bradshaw band in 1939.34
Harris and Monk befriended a young drummer from Pittsburgh named Kenny Clarke. Kenneth Spearman Clarke (nicknamed “Klook”), born almost four years before Monk, began his musical career playing piano and organ in the church. He eventually took up the drums, toured with bands in the Midwest, and made his way to New York City with a pianist Call Cobbs. In 1936, Clarke formed a short-lived trio with Cobbs and Clarke’s brother Frank—a bassist who played in the style of Jimmy Blanton—and he gigged with various groups in the city, landing jobs with orchestras led by Edgar Hayes and Teddy Hill (1939–1940).35 At night he worked with veteran musicians, but by day he hung out with Thelonious and Harris, and sometimes he brought along another pianist whom he knew from Teddy Hill’s band—the Panamanian-born Sonny White (né Ellerton Oswald).36 Monk played with these guys and presumably worked out some of his own ideas. And he played quite a bit alone, working on new interpretations of standard tunes and composing his own songs—compositions still several years away from being recorded. As a sounding board for his own music, he always pressed his brother and sister for their opinion. Marion recalled, “He’d say: ‘Say, Sis, listen to this,’ and so I’d listen to it. If it was okay I’d say [so], you know?” On the other hand, if the music didn’t move her, she was honest about it, and he treated her criticisms seriously.37
Armed with a union card and a growing number of professional contacts, especially in Harlem, Monk began working in earnest in 1939. He formed a quartet consisting of Jimmy Wright on tenor, Keg Purnell on drums, and the mysterious bass player known only as “Massapequah”—the name of a hamlet on Long Island.38 Each of them lived in Harlem at the time. Jimmy Wright, who would later record with Louis Jordan and distinguish himself as both a reed player and drummer on early R&B recordings, began as a Coleman Hawkins imitator.39 Keg Purnell was a swing drummer with an easy touch who hailed from West Virginia. Though just two years older than Monk, he was a veteran of the music scene, having worked with King Oliver in 1934–35 and having led his own trio. He was only with Monk for a few months before joining Eddie Heywood, Jr., as a member of Benny Carter’s band.40
There are no recordings of the quartet. No doubt Thelonious played in the stride style with a lot of modern dissonance thrown in. They might have played one or two of Monk’s original tunes, since he had already begun writing, but most likely they played standards: “Honeysuckle Rose,” “I Got Rhythm,” “Indiana,” “Body and Soul,” and the like. As the group’s leader, Monk earned a bit more than his sidemen, but not much.
America was still in the throes of the Great Depression, and African-Americans were especially hard hit. Unemployment was high and many families in New York still depended on work relief projects created by FDR’s New Deal agencies. One of those agencies, the Works Progress Administration (WPA), hired musicians for various projects, but its low wages prompted Local 802 to picket their offices.41 The union had suffered a decade of setbacks caused by the closing of venues, a dramatic decline in record sales, an increase in the number of musicians moving to New York in search of job opportunities, and the rise of sound film. Once “talkies” replaced the old silent pictures, over 3,200 New York pit musicians were suddenly out of work. The union waged a campaign culminating in a strike, to return live music and vaudeville shows to the movie theater, but it ended in utter disaster in 1937, when it became clear that the rest of the working class would not support them. In a prequel to a debate fifty years later about using acoustic synthesized music on Broadway, the union was struggling against an inevitable tide of economics and consumers. Working people not only preferred sound films but appreciated the price of the ticket, which was lower without the live talent. Freed of wages and union regulations governing musicians’ hours, theater owners could show films all day long, and the jobless could escape the cold, the heat, or their general frustrations by spending their afternoons at the movies for a paltry twenty-five or fifty cents.42 Joblessness became such a problem in New York that Local 802, with the help of leading philanthropists and patrons of the arts, launched a Musicians’ Emergency Fund to provide relief for out-of-work musicians.43
Few black musicians uptown benefited from the Emergency Fund, and the union did little to challenge racial discrimination in the music industry. Lucrative studio jobs remained the preserve of white musicians. The union often looked the other way when unscrupulous record labels employed non-union black musicians to make “race records.”44 Despite the immense popularity of the bands led by Cab Calloway, Count Basie, Duke Ellington, Jimmie Lunceford, Lucky Millinder, Chick Webb, and others during the mid-to-late 1930s, black bands were paid significantly less than white swing bands. Throughout the 1930s and ’40s, black musicians unsuccessfully challenged the union’s policy of setting its pay scale considerably lower for Harlem dance halls and clubs than for venues in other parts of the city.45 Worse, African-American bands were virtually banned from the elite hotels from which many live radio broadcasts took place. Limited radio airplay meant fewer record sales and less publicity. Absent lucrative hotel gigs and commercially-sponsored radio spots, the black bands—including the Ellington Orchestra—had to endure a grueling schedule of one-night stands to make ends meet. Having just spent two years on the road, Thelonious knew exactly what this meant: Jim Crow hotels, rooming houses in black communities, and the ever-looming possibility of racial hostility.46
By the time Monk turned “professional,” it appeared as though the black big bands were on the verge of disappearance. In 1940, prominent music magazines as well as the black press ran several ominous articles predicting their death. In one headline, Down Beat magazine asked: “Are Colored Bands Doomed as Big Money Makers?”47 African-American bands simply could not compete with the new generation of white swing bands led by the likes of Benny Goodman, the Dorsey Brothers, and Gene Krupa, who sounded more and more like the black bands and could make money much more easily. They not only adopted—or at least gestured toward—the aesthetic principles of black dance music, but they hired black arrangers to write their charts. Benny Goodman employed Fletcher Henderson, Tommy Dorsey hired Sy Oliver from Jimmie Lunceford’s band, and both Paul Whiteman and Jimmy Dorsey relied on Don Redman’s arrangements.
The history of American popular music is often depicted as a series of stories of white musicians imitating black innovators and getting rich, from Benny Goodman to Elvis to Eminem. Of course, the story is more complicated. Beginning with Benny Goodman, the popular white swing bands began hiring black musicians. Many critics and fans applauded Goodman’s decision to bring arranger/pianist Fletcher Henderson, pianist Teddy Wilson, vibraphonist Lionel Hampton, and guitarist Charlie Christian into his band, characterizing this move as a triumph of integration. For many black musicians, however, it seemed more like “raiding” their most talented and dynamic musicians.48
Even if Monk had wanted to join one of the major bands in the forties, jobs were few and far between, and ultimately he lacked interest. He played briefly in bands led by Lucky Millinder, Skippy Williams, and Dizzy Gillespie, but “[The big] bands never did knock me out,” he told George Simon in 1948. “I wanted to play my own chords. I wanted to create and invent on little jobs.”49 A big-band piano player was expected to provide rhythmic and harmonic support for the horn and reed sections, and occasionally take a chorus or half-chorus solo. This is not what Monk had in mind when he got his union card. And he had no intention of going back on the road again. Most of his “little jobs” were in the small bars and dives in Harlem. Bassist Red Callender recalled seeing Monk playing at Mack’s in Harlem in this period. “Bedbugs would be crawling all over the joint, but Thelonious Monk was sitting at the piano. . . . Before the advent of so-called bebop, I’d hear all Monk’s licks and be thrilled with it. After his sets, we walked around Harlem together.”50
Harlem was becoming Monk’s second home. Lucky for Thelonious, his best friend Sonny, along with Nellie and Skippy, returned from their aunt’s house in Connecticut in 1938 and moved to Harlem. They returned to the city in part because “the aunt was really abusive, abusive in strange ways.”51 Also, Sonny made a promise to his sweetheart, Geraldine, to find his own home. Sonny rented a private house on 136th Street and Seventh Avenue. The property was sizable and well kept, and Sonny got it for a song because the owner, a notorious numbers runner named Ford, felt sorry for their having lost their mother so young. The paint on the walls was hardly dry before Sonny and Geraldine tied the knot on the 27th of June and she joined the clan uptown.52 Eight days before Christmas, they added one more resident: their first-born daughter, whom they named Jackie. Their second-born, also a girl-child, arrived on May 4, 1940, and they named her Judith.53
Sonny and Geraldine were still responsible for Skippy, who was only fourteen when they returned to New York. Nellie, on the other hand, was sixteen, practical, and quite independent. With two more years of high school left, she decided her immediate future lay in dressmaking, perhaps clothing design, so she enrolled in Central Needle Trades High School, one of the city’s leading industrial schools. Although it had been beset with budget issues in the mid-1930s, the school had made a remarkable comeback and almost overnight grew in popularity. By the time she started classes in 1938, Central Needle Trades had just moved to temporary quarters on Sixth Avenue and 23rd Street with the intention of moving into a brand new multi-million-dollar, eleven-story facility on 24th between Seventh and Eighth Avenues.54 She did not rule out college; on the contrary, Nellie was determined to further her education one way or another, but given their current financial reality, learning marketable skills and finding a decent job was paramount.
Shy little Nellie was becoming a woman now, and it seemed as though everyone noticed except Thelonious. He was far more preoccupied with having his old running buddy Sonny back in town, and the friendly uptown house was a bonus. Now he had a place to crash on late, cold nights when he didn’t feel like trekking back to West 63rd Street on the IRT. Although he never moved in with Sonny and his family, he was such a frequent visitor that he might as well have changed his mailing address. Geraldine recalls too many times when Thelonious would just come through the window in the middle of the night, wanting to sleep or, worse, to talk. “At that time, I got mad at him because he would do so many outlandish things. He would come in and wake you up if you’re sleeping. ‘Get up!’ And I would tell him, ‘Thelonious, if you don’t leave me alone.’ And after he would get everybody awake, then he would go to sleep.”55
Monk worked intermittently throughout 1940, and he found a hospitable community of like-minded musicians hanging out at a club inside the Cecil Hotel on 118th and St. Nicholas. The place was called Minton’s Playhouse. In January of 1941, the management offered him his first regular job as the house pianist. This small Harlem club was about to become a jazz legend.