Why Sinatra Matters
“The first thing he said was, ‘Yes, I remember that day when you couldn’t get out those words.’”
Dorsey signed him to a long-term contract for $125 a week, which Sinatra needed since Nancy was now pregnant with their first child. But it wasn’t easy to leave Harry James. The handsome, mustached trumpet player also had a contract with Sinatra, but he was a decent man; he knew his own band wasn’t making money and that Dorsey, a “rich” band, could pay the young singer steadily and well. He tore up his contract and wished Sinatra all the luck in the world. They were still friends when James died in 1983.
“That night the bus pulled out with the rest of the boys at about half-past midnight,” Sinatra later told Douglas-Home. “I’d said goodbye to them all, and it was snowing, I remember. There was nobody around and I stood alone with my suitcase in the snow and watched the taillights disappear. Then the tears started and I tried to run after the bus.”
He didn’t catch it. The James band went to play a gig in Hartford, and Sinatra took a train to New York. From there he went off to three years of school at Dorsey University. Every night he listened to, and learned from, some of the best musicians in the country: pianist Joe Bushkin, drummer Buddy Rich, Berigan and his replacement as lead trumpet, Ziggy Elman (a defector from the Goodman band). Sy Oliver taught Sinatra how to ride or glide over the rhythm base of a tune, not repeat it in his vocals, which was a kind of musical redundancy. Like Sinatra, these musicians had all been formed by Prohibition and the Depression, and the new vocalist liked their style. They were hard-drinking, tough-talking, and dedicated to the music. They smoked cigarettes. They chased women. They gambled. They cursed. And they played at the top of their talent, or were sent packing by the remorseless Dorsey.
Sinatra started as one of the Pied Pipers, the band’s singing group, whose female star was Jo Stafford. She later remembered Sinatra, walking on stage for the first time, as “a very young, slim figure with more hair than he needed. We were all sitting back – like, ‘Oh, yeah, who are you?’ Then he began to sing.” After four bars Stafford knew that she had better listen closely. She thought, “Wow! This is an absolutely new, unique sound.” As she elaborated later: “Nobody had ever sounded like that. In those days most male singers’ biggest thing was to try and sound as much like Bing as possible. Well, he didn’t sound anything like Bing. He didn’t sound like anybody else that I had ever heard.”
Sinatra swiftly gained the respect of the other members of the band, even those who were friends of the departed Jack Leonard. He had a variety of troubles with Buddy Rich, a loner who considered himself the band’s feature attraction, with some reason (many consider him the greatest white drummer of the century). Sinatra even heaved a water pitcher at Rich backstage, sending shards of broken glass scattering and splashing Stafford. But they were also friends, rooming together on the road, where Sinatra would absorb Rich’s knowledge of rhythm and tempo. As his confidence grew, Sinatra strengthened and refined his technique by listening to all the musicians, but above all to Dorsey. And he made records with the band. The first two were recorded on February 1, 1940 (“The Sky Fell Down” and “Too Romantic”); eighty-one others would follow.
It wasn’t always easy. The son of a music teacher, Dorsey was Irish, tough, something of a martinet. A few years earlier he had fought with his older brother, Jimmy, another fine musician, and broke up their band to go off on his own. Tommy built his own orchestra into a commercial and artistic success through a combination of will and musicianship. He built his sound around his own sweet trombone playing, as exemplified by his theme, “I’m Getting Sentimental Over You,” but also willingly turned the spotlight over to soloists and vocalists. He insisted on perfection from the band members and had no tolerance for the unkempt semi-bohemian styles that many musicians affected. He wanted his men to be clean-shaven and even held inspections before gigs. For the most part, the men responded; the members of the Dorsey band swaggered a bit, convinced of their superiority over other bands. But Dorsey, like Buddy Rich, was also a loner. That quality obviously touched Sinatra in ways that had nothing to do with music.
“Tommy was a very lonely man,” Sinatra told Douglas-Home. “He was a strict disciplinarian with the band – we’d get fined if we were late – yet he craved company after the shows and never really got it. The relationship between a leader and the sidemen, you see, was rather like a general and privates. We all knew he was lonely, but we couldn’t ask him to eat and drink with us because it looked too much like shining teacher’s apple.”
Sinatra remembered finally asking Dorsey to have dinner with him and another musician; Dorsey agreed and was touchingly grateful. “After that,” Sinatra said, “he was almost like a father to me.” Dorsey would, in fact, be godfather to Sinatra’s daughter Nancy. During these three years Sinatra absorbed many lessons from his surrogate father. One was about spacing a show, always meticulously planned by Dorsey. The Dorsey band wasn’t just playing music for dancers, it was also presenting a show, one that demanded its own structure, intelligent variations of up-tempo tunes and ballads, a sustained presentation that would leave the audience with a sense of completion.
Sinatra told me about Dorsey: “He put together a show like it was one long piece of music, or like an album – this was before the LP, and you couldn’t do records that way – with different moods and movements leading to a crescendo. He knew how to shift a mood so it didn’t all sound the same and bore the ass off the audience. It was dance music, first and foremost. But it was more than that. I always kept that in mind later, for my own shows and albums. Tommy didn’t spell it out to us, but he didn’t have to. It became part of you, just from doing it. Seven shows a day, sometimes, if you worked a theater. Three shows a night, if the gig was a dance somewhere. It became part of you.”
Dorsey’s own work on the trombone had a lasting influence on Sinatra’s style. There has been much discussion of the way Sinatra watched Dorsey’s tricks of breathing, in order to sustain long phrases. The writer and lyricist Gene Lees dismisses most of that as a myth. But in his essay on Sinatra in Singers and the Song II, Lees describes superbly what Dorsey’s real influence was on Sinatra the musician. He writes of Dorsey:
“He did … have remarkable breath control, and his slow deliberate release of air to support long lyrical melodic lines was indeed instructive to Sinatra and still worth any singer’s attention. Dorsey would use this control to tie the end of one phrase into the start of the next. Sinatra learned to do the same.”
Lees cites, as an example, their 1941 recording of “Without a Song.”
“Since Dorsey’s trombone solo precedes the vocal, the record provides an opportunity to observe how Sinatra was learning from Dorsey, and how far he had come from ‘All or Nothing at All.’ At the end of the bridge, Sinatra goes up to a mezzo-forte high note to crest the phrase ‘as long as a song is strung in my SOUL!’ But he does not breathe then, as most singers would. He drops easily to a soft ‘I’ll never know …’ This linking of phrases between the inner units, learned from Dorsey, gave Sinatra’s work a kind of seamlessness.”
To build up his breath, Sinatra spent long hours in swimming pools, often under water, and when not on the road used the outdoor track at a school in Jersey City. Dorsey’s long lines, his legato sound, his use of glissando movements, abruptly plunging deep into the lower register for certain effects – all marked Sinatra. But Sinatra could do things Dorsey could not do, for the simple reason that he was using the English language, with its creamy vowels and abrupt consonants. And he used it in a way that can only be described as urban. Again, Lees describes this very well:
“When you sing a long note, it is the vowel you sustain, almost always. Certain of the consonants, voiced or voiceless, cannot be sustained: b and its voiceless counterpart p, d and t, g and k. You cannot sing thattttt. It is impossible. You must sing thaaaaat or cuuuuup. Or taaaake. But certain other consonants, voiced and unvoiced – v and f, z and s – can be sustained,
being fricatives, although I find the effect unattractive. You cannot sustain the semivowels w and y. But there are four semivowels that can be sustained: m, n, l, and r. Now, just as Spanish has long and short forms of the letter r – a double rr, as in perro, is rolled – correct Italian enunciation requires that you slightly sustain all double consonants. And Sinatra always recognized this principle, whether because of his Italian background or not. You hear it when he extends the l in Alllll or Nothing at Alllll.”
In addition, Sinatra’s delivery of certain words acquired a subtle New York flavor, Lees points out, because he “dentalized” ts and ds. That is, like many people from the New York area, he formed each consonant with the tongue against the teeth, rather than the gum above the teeth. In words like dream or tree, he could instantly pull it away, softening the following r. This made for a more fluid enunciation of many words and prevented the popping of consonants when using the microphone. This was never a problem for opera singers, or Broadway belters, but was essential when using a microphone in a recording studio, or the even clumsier microphones used on bandstands.
During this period Sinatra worked hard at mastering the microphone, knowing that it was his musical instrument. There were no portable mikes in those days; each microphone was attached to a stand. Almost all singers stood rigidly facing the mike and used their hands for dramatic emphasis. It was as if they were singing to the microphone, not the audience. Sinatra changed that, gripping the stand itself, and then, according to Lees, “moving the mike in accordance with what he was singing. And he was the man who developed this technique.” Movement was crucial to the performance. “Sinatra gripped the stand and drew the microphone toward him or tilted it away according to the force of the note he was putting out at any moment.”
Sinatra was then able to establish greater intimacy with the audience, shifting his attention from one young fan to another, but making each feel like the specific object of his attention. He never lost that ability to connect. It was at the heart of his intimate style. These factors combined to make the unique Sinatra sound: breath control and seamlessly sustaining notes; the subtlety of the New York speaking voice refined by impeccable diction; a natural, intimate style made possible by intelligent use of the microphone. Dorsey also established for Sinatra a standard of professional excellence that would endure for a lifetime.
Nobody can speak with absolute confidence about the artistic undertones of the Sinatra style. He spoke later in life about the effect of Billie Holiday on his work, citing her phrasing. I’ve listened to a number of tunes that were recorded by both, and I don’t hear that effect. But one night he said something about Lady Day that did make sense.
“What she did was take a song and make it hers,” Sinatra said. “She lived inside the song. It didn’t matter who wrote the words or the music. She made it hers. All the jerks who fucked her and left her. All the nights strung out on junk. All the crackers that treated her like a nigger. They were all in her music. That’s what she made out of those songs. She made them her story.”
At his best (and he sometimes made choices that were awful, or had them forced upon him) Sinatra did the same. He inhabited a song the way a great actor inhabits a role, often bringing his own life to the music. As a young singer, there wasn’t as much life to draw upon, but it did have a large share of hurts, some because he was Italian American, some because he felt he didn’t have enough formal education, others because of the way he grew up as an only child. Right from the beginning, he had a profound understanding of human loneliness. Some of this he must have also drawn from the silent presence of his father, the inconstant exuberance of his mother. Some of it must have been emphasized when he joined the company of the orchestras, living day and night with talented men who had lived other kinds of lives, rich with the presence of family.
“I’d be in the bus, and the guys’d be sleeping or drinking or talking,” he said once. “And I’d look out the window and see these houses with the lights on and wonder how they all lived. The houses looked warm. Safe. You know, normal. I was still a kid, but I knew that it was too late for me to have that kind of life.”
Riding those buses through America, Sinatra also must have known that he could never be a sideman, a part of a group, all for one, one for all. He wasn’t raised that way. He was raised to work solo.
III. When the bombs dropped on Pearl Harbor and the Americans finally entered the war, Sinatra was poised to complete a process that had started with Fiorello La Guardia and was solidified by the baseball triumphs of Joe DiMaggio: the integration of the children of Italian immigrants into American life.
A progressive Republican (in opposition to the anti-Italian bosses of Tammany Hall), La Guardia had been elected mayor of New York in 1933 after a splendid career as the first Italian American ever elected to Congress. In some respects, he was not typical of the immigrant experience. He was the son of a Jewish mother from Trieste and a Protestant father who was born in Foggia, in II Mezzogiorno. Born on Sullivan Street in New York’s Little Italy and raised in Arizona where his father served as a U.S. Army bandmaster, Fiorello spoke Italian and Yiddish and had worked as an interpreter at Ellis Island, an experience that made him a lifelong defender of immigrants. He fought for unions. He fought against all forms of racism. He battled anti-Semitism. As a congressman, he had warned the country about the dangers of Prohibition, urging them to reject the Volstead Act. He predicted that it could not be enforced. Nobody listened, but he was right. Fiorello had passion and language and courage. He became the greatest mayor of New York’s twentieth century, a star on radio, a national figure. New Yorkers were not alone in thinking about him with affection and respect.
DiMaggio was a year older than Sinatra, the son of immigrants from Isola delle Femmine, a tiny fishing port on the northern coast of Sicily, just west of Palermo. His father arrived at Ellis Island in 1902, the mother the following year, and they soon moved to California, where there was work for an honest fisherman. Joe, the oldest of nine children, arrived at Yankee Stadium for the 1936 season and had a wonderful year for a twenty-one-year-old, batting .323 and hitting 29 home runs. He was shy, even aloof, but had uncommon style, both as a player and as a man. As he matured, he got even better. He hit with power and for average and was a superb outfielder. In 1941 he set a record that has never been broken: he batted safely in 56 consecutive games.
In those years before television, DiMaggio was known all over America. He endorsed products. His face adorned magazine covers. Songs were written about him. That awful phrase “role model” wasn’t used in those days; it was enough to be called a hero. DiMaggio was one of them. An American hero. And an Italian American hero too. There were other Italian American baseball players, including Tony Lazzeri before him, and contemporaries such as Frank Crosetti and the shortstop Phil Rizzuto. But DiMaggio was more than a baseball player; he was the epitome of grace. American grace. Italian American grace. Nobody paid much attention to the fact that he kept silent about discrimination against other Americans, including Italian Americans and blacks. That was Joe. As Gay Talese has observed: “He was and has remained an interior man, ever distant, cautious, never in the forefront with a social conscience. At best, a male Garbo.”
To these triumphs of Italian Americans in politics and sports was added another: the sudden arrival of Frank Sinatra as the biggest star in show business. That trio – La Guardia, DiMaggio, and Sinatra – changed forever the way Americans saw Italian Americans. For the first time, Americans with other ethnic origins wanted to be like these children of the Italian migration. And their accomplishments changed the way Italian Americans saw themselves.
The story of Sinatra’s explosive arrival as a major American star is, again, a familiar one, a great show business drama played out on the stage of the Paramount Theater in New York. Timing had something to do with it. The war effort was then under way; the Depression was over; and men and women were, suddenly and astonishingly, earning more money in war plants
than they had ever imagined possible. (My father went from a $19-a-week job to one that paid $102.) That meant there was a lot more money to spend on entertainment. And as the young men went off to boot camp or basic training, there were a lot more lonely women in the land.
Sinatra and the Dorsey band were in Hollywood, making a small film called Ship Ahoy, when the airplanes of the Japanese Imperial Navy ended the Depression by bombing Pearl Harbor. Twice Sinatra tried to enlist in the army, and each time he was turned down because of that punctured eardrum. But he was increasingly anxious to go out on his own, convinced that there would be a huge audience for a new kind of music that went beyond the big band format. It would be built around the singer, as vigorous as swing but made lusher, more romantic with the use of strings. Sinatra didn’t want another singer to get there first. Perry Como from the Ted Weems band. Ray Eberle from Glenn Miller. Or even Jack Leonard.
“I didn’t want to be left behind,” he said later. “I wanted to get there first.”
In January 1942, with Dorsey’s reluctant permission, the impatient Sinatra cut four sides for the cut-rate Bluebird Records, using Axel Stordahl as the arranger and employing strings and woodwinds for the first time. These were the first records made on his own, without the dominating accompaniment of a star big band. The tunes were “Night and Day,” “The Night We Called It a Day,” “The Song Is You,” and “The Lamplighter’s Serenade.” The first three would remain part of his repertoire for the rest of his life. He was exultant. Stordahl remembered sitting with Sinatra after the session, listening to acetate disks: “He just couldn’t believe his ears. He was so excited.”
Those records enhanced his reputation and found their way to another huge emerging market: jukeboxes. They also increased his obsessive desire to escape from Dorsey. His 1940 recording with Dorsey of “I’ll Never Smile Again” had spent twelve weeks as the number one song on the Billboard charts, and the same combination had hits with “Stardust,” “Trade Winds,” “Our Love Affair,” “This Love of Mine,” “Dolores,” and “Oh, Look at Me Now.” But those were all perceived as Tommy Dorsey hits, not Frank Sinatra hits. It was the music he made with Stordahl for Brunswick that came closest to what Sinatra wanted to do. He also knew that he had a real opportunity now to fulfill the boast he’d made after seeing Bing Crosby perform in 1935. That process had already begun. In May 1941 Billboard named him the nation’s top male vocalist. The same year’s Down Beat poll (released in January 1942) also encouraged Sinatra’s ambition; for the first time since 1937 Bing Crosby had lost the number one position. The new favorite was Frank Sinatra. The time to leave was now.