To understand how an inexperienced young lady from Canada could take the world by storm by doing the impossible—writing words and music to a heart-gushing requiem that would give young Frank Sinatra’s career a rocket boost into the stratosphere—well, you need to get your head around the times back then. So, let’s take a little meander down memory lane.
It’s the 1930s and 40s, and music rules like no time before or since. The big bands of the era are filling the ears, eyes, and minds of just about everybody who will listen, regardless of race, creed, or color. From Glenn Miller to Benny Goodman to Artie Shaw to Count Basie to Jimmie Lunceford to Duke Ellington to the aggregation led by the guy they would come to term “the General Motors of the Band Business”—Tommy Dorsey—it is a time of musical rewards all around.
This Dorsey was an interesting cat, an American original. Born in November of 1905, he’d made his entree into the music biz because his father, a coal miner, recognized mining offered a dead-end future and stated, “I’ll do anything to keep my sons out of the mines.” And so, the stage was set for Tom to join his older brother Jim in establishing their musical talents by playing in local concerts and parades. Jimmy would soon gravitate to reed instruments, while Tommy came to favour brass.
So, what was the relationship like between the siblings? “Well, it was a very complicated, very Irish, kind of thing,” says Peter Levinson, author of Tommy Dorsey: Livin’ in a Great Big Way.
“Very close as brothers, and yet feuding and fighting, and when I say fighting, I mean fist fighting, often,” Levinson comments. “And if anyone came to separate the two, then the two brothers would fight that person. It was their own fight. No one else was supposed to get in between them at any time. There was a great respect, a great love, but also a great jealousy.”2
Figure 3: Tommy Dorsey
Now, Tommy Dorsey was a piece of work. Levinson tells us that he drank too much, he was a womanizer—even being suspicious of his own wife while he was cheating on her—and there were many other things not to like about the man. “But he also had tremendous charm and he could take care of people,” the author says.
And with Frank Sinatra, it was a tumultuous relationship between him and Dorsey from the start. Still, the singer learned a great deal from his mentor.
Levinson:
There’s a key quote that I got from Vince Falcone, who played piano for Sinatra during the ’70s and later in the ‘80s, and who said to me, “You know,” Frank said, “The two most important people in my life have been my mother and Tommy Dorsey.3
It should be said that both the Dorsey boys knew their way around a bottle of hooch. But Tommy experienced an attack of appendicitis and hospitalization in June 1933. Reading the tea leaves, he vowed to stop drinking, an oath from which his older brother abstained, and the two musicians went their separate ways.
Tommy, who by now went with the nicknames Mac and TD, was a driven soul. It didn’t take long for “Tommy Dorsey and his Orchestra” to make their debut in October 1935 at the French Casino in New York. Soon, he’d signed a recording contract with RCA for its Victor label.
Dorsey dreamed big and was not afraid to spend money to get to the top. He hired singer Jack Leonard and trumpet player-arranger, Axel Stordahl (who would go on to fame with Frank Sinatra as the singer’s full-time arranger after he left the Dorsey band in 1943). Soon, Tommy’s orchestra was selling records, making big impressions with several number one hits and being featured on radio and in personal appearances, including starring gigs on NBC’s radio program The Magic Key of RCA. By July 1937, the Dorsey band had become the headliner on the new Raleigh-Kool Show, introducing Tommy as “That Sentimental Gentleman of Swing.”
Fast forward to the summer of 1939: TD is firmly established. His engagement at the coveted Hotel Pennsylvania in New York has justifiably positioned him at the top of the top. But Dorsey is restless. Yes, his popularity has become significant: yet he’s still always on the lookout for new and challenging directions. “Being competitive was not enough,” according to Dennis M. Spragg, writing in the University of Colorado’s Glenn Miller Archive. “He wanted to win. He wanted to be number one.”
Tommy was smart enough to accept that great singers could make his band more appealing to the masses. And so, hearing that young Frank Sinatra had joined trumpeter Harry James and his orchestra and was beginning to show promise, he kept his eye on the ambitious kid. As James Kaplan tells us in his biography Frank: The Voice, “Harry James was a hot artist: a hepcat, a weed-puffing wild man. He was also a strangely self-defeating character—alcoholic, remote, and persistently broke. That summer, he lost everything he had in a settlement over an auto accident.”
James had offered Sinatra a contract of $75 a week (neglecting to reveal that there might be some weeks when he wouldn’t have the dough to pay up). He also wanted his new protégée to change his brand: Sinatra was too “Eye-talian.” “How ’bout Frankie Satin?” the bandleader suggested. “It’ll go good with that nice smooth voice of yours.”
However, Frank Sinatra stood firm, commenting years later, “Can you imagine? Is that a name or is that a name? ‘Now playing in the lounge, ladies and gennulmen, the one an’ only Frankie Satin.’ If I’d’ve done that, I’d be working cruise ships today.”
Kaplan:
The Voice—might as well start capitalizing it here—was simply working its spooky subliminal magic. Did it help that the singer was clearly in need of a good meal, that his mouth was voluptuously beautiful, that his electric-blue eyes were attractively wide with fear and excitement, that he knowingly threw a little catch, a vulnerable vocal stutter, into his voice on the slow ballads? It helped. It whipped into a frenzy the visceral excitement that his sound had started. But the sound came first. There was simply nothing like it.4
TD’s always sharp antennae told him that James was having a hard time making a go of it. As it happened, both his band and James’ were booked into Chicago at the same time, so Tommy schemed to meet with Sinatra. His pitch was simple: $125 a week versus James’ $75 stipend. For Sinatra, whose wife Nancy was pregnant with their first child, the raise would be welcome. But not nearly as encouraging as riding up that elevator of renown to singing with the top band in the land. Now, that was something money couldn’t buy.
Around the same time, Mac offered employment to a Southern California singing group known as “the Pied Pipers.”
With the addition of this vocal quartet, plus Sinatra, Tommy Dorsey knew he was now poised to make history.