Why Sinatra Matters

4 THE SONG IS YOU

HIS FINEST ACCOMPLISHMENT, of course, was the sound. The voice itself would evolve over the years from a violin to a viola to a cello, with a rich middle register and dark bottom tones. But it was a combination of voice, diction, attitude, and taste in music that produced the Sinatra sound. It remains unique. Sinatra created something that was not there before he arrived: an urban American voice. It was the voice of the sons of the immigrants in northern cities — not simply the Italian Americans, but the children of all those immigrants who had arrived on the great tide at the turn of the century. That’s why Irish and Jewish Americans listened to him in New York. That’s why the children of Poles in Chicago, along with all those other people in cities around the nation, listened to him. If they did not exactly sound like him, they wanted to sound like him. Frank Sinatra was the voice of the twentieth-century American city.

In life even the mature Sinatra would sometimes speak in the argot of the street. He could be profane, even vulgar. The word them could become dem, and those could become dose. It depended on the company. But in the songs the diction was impeccable. The children of the Italians, the Irish, and the Jews wanted to believe that they could express themselves that way, and many of them did. In my Brooklyn neighborhood, many of us understood that we were not prisoners of the Brooklyn accent, because Sinatra’s singing refused to use it. And he was like us. His diction was something that Sinatra learned early, from the movies.

“I’d go to the movies, and hear the leading man speaking English — not just Cary Grant, but Clark Gable and all the other guys — and I knew that my friends and I were talking some other version of the language,” he said once. “So I started becoming, in some strange way, bilingual. I talked one kind of English with my friends. Alone in my room, I’d keep practicing the other kind of English.”

His taste in music was formed early. He grew up listening to and memorizing the words and music of the great popular composers and lyricists of the first forty years of the twentieth century. These included Jerome Kern, Rodgers and Hart, Cole Porter, Harold Arlen, and Johnny Mercer, to mention only a few of this extraordinary generation. Many were themselves part of the immigrant saga. Arthur Schwartz was the grandson of a buttonmaker from Russia. Harry Warren was the child of immigrants from Italy. Yip Harburg’s parents were from Russia. Irving Berlin, author of “God Bless America” and a thousand other tunes, was himself an immigrant from Siberia. All were very American, creators of most of those songs that became known as the “standards” of twentieth-century American music.

As the reigning citizens of Tin Pan Alley, they wrote music for the Broadway theater. They wrote for musical revues. They wrote for the movies. Above all, they were city people, and their audiences were composed of city people. Often building on forms derived from African American rhythms, adapting European melodic structures and harmonies, the best of their music was full of wit, regret, insouciance, and sly humor. During Prohibition the music celebrated good times and a sophisticated hedonism, becoming the unrecorded sound track of the speakeasies. When the Depression hit, there was a chastened undertone to the music, a feeling of rue (as there was in the late writing of Scott Fitzgerald). Some writers were capable of biting social commentary, as in Harburg’s “Brother, Can You Spare a Dime?” Most of the time, the attitude was less direct. Perhaps the apocalypse was here, the songs declared; if so, let’s dance. That music was absorbed by the men and women of an entire generation. Sinatra was one of them, but he had begun to hear the music in a new way.

He heard it through the diverse filters of the streets of Hoboken, his own childhood, his personal solitude, and above all through the masculine street codes forged in the years of Prohibition. When the Noble Experiment ended on December 5, 1933, Americans didn’t revert in the morning to the kind of people they were before Prohibition started; they had emerged from the era a lot more cynical and a lot tougher, qualities that would get many of them through the Depression. Sinatra applied some of those attitudes to his music.

If love lyrics were too mushy, he could sing them and make wised-up fun of the mush, and still, in some part of the self, acknowledge that there was some truth to the words. He could be tender and still be a tough guy. Ruth Etting could sing her weepy torch songs, but for men, whining or self-pity was not allowed; they were forbidden by the male codes of the city. Sinatra slowly found a way to allow tenderness into the performance while remaining manly. When he finally took command of his own career, he perfected the role of the Tender Tough Guy and passed it on to several generations of Americans. Before him, that archetype did not exist in American popular culture. That is one reason why he continues to matter; Frank Sinatra created a new model for American masculinity.

Sinatra was not, of course, a jazz singer, but his process resembled the way many jazz musicians worked. The best of them listened creatively to the tunes of Tin Pan Alley but heard them through the filter of their own experience, which was dominated by being black in segregated America. They transformed those songs, edited them, reinvented them, found something of value in even the most banal tunes. The instrument didn’t matter. Over the years Louis Armstrong and Miles Davis found something different in the same tunes; so did Clifford Brown and Dizzy Gillespie, Lester Young and Ben Webster, Coleman Hawkins and Dexter Gordon. They understood the specific lyrics of what had become known as American standards and the general intentions of the songs; they insisted on making them more interesting as music, more authentic, more personal, finding a subtle core that more closely resembled the blues. The results could be entertainment, a transient diversion from the hardness of life; but the songs could be art, too, digging deep into human pain and folly. They could also be both. But these musicians approached the music with a seriousness that was pure. Sinatra worked in a similar way. He didn’t play trumpet, trombone, saxophone, or piano; he rarely composed music or wrote lyrics; but he did function as a musician.

“I discovered very early that my instrument wasn’t my voice,” he said to me once. “It was the microphone.”

II. In the tradition of the Old Country, Frank Sinatra served a long apprenticeship. He seems to have conceived the notion of being a professional singer when he was fifteen. Again, the instinct to create legend or myth obscures the facts, and not even Sinatra was a reliable witness to his own beginnings, and he knew it.

“Sometimes I think I know what it all was about, and how everything happened,” he said one rainy night in New York. “But then I shake my head and wonder. Am I remembering what really happened or what other people think happened? Who the hell knows, after a certain point?”

One thing that really happened was the discovery that he actually did have a voice and could sing. I reminded him once of the story that Rocky Marciano, the old undefeated heavyweight champion, used to tell. He said that when he first knocked out a man in a gymnasium when he was a kid, it was like discovering he could sing opera.

“Hey,” Sinatra said, “when I first realized I could sing a song, I felt like I’d just knocked out Jack Dempsey.”

But in Hoboken in 1930 there were dozens of young men (and surely a few women) who could sing well. They could carry a tune. They could remember the words. Few of them thought they could become stars. That required an act of the imagination, the kind of gleaming vision that is often unique to artists, along with the type of will that is sometimes mistaken for arrogance. Above all, it took guts. To walk out of the safety of the parish is never easy; to do so during the Depression was an act of either foolishness or courage. And yet a small number of people chose to go out and try to make it in America, no matter what the odds against them.

“There really was nothing to lose,” Sinatra said later. “Yes, you might fall on your ass. But so what? You could always work on the docks or tend bar. What was important was to try.”

The lure of big-time success was underlined by the grinding horrors of the Depression. Crime was one way out; with audacity and a gun, a kid might become a big shot. But talent was another. By the early 1930s the radio and the phonograph record, along with sound movies, were creating the first national pop singing stars. One was Russ Columbo, who had a light operatic voice and made an immense hit of “Prisoner of Love.” He showed that an Italian American could be accepted beyond the boundaries of the parish, but his career was cut short in 1934 by his accidental death while cleaning an antique pistol. Rudy Vallee was another early star. But his voice was light and tremulous, he looked a bit goofy, and in personal appearances he used a megaphone; he couldn’t play college sophomores forever. In the cities of the Northeast there weren’t many college sophomores to identify with him anyway. Certainly kids like Frank Sinatra never wanted to grow up to be Rudy Vallee. But Bing Crosby was an altogether different model.

“You can’t imagine now how big Crosby was,” Sinatra said in the 1970s. “He was the biggest thing in the country. On records. On the radio. In the movies. Everybody wanted to be Bing Crosby, including me.”

Crosby did understand the microphone — and the camera. He knew he didn’t have to hit the second balcony with the belting style forced upon Broadway singers. The microphone permitted a more intimate connection with the audience. He didn’t have to italicize his acting in movies, the way theater-trained actors did; the close-up allowed him to be natural. Crosby was relaxed, casual, and very American.

The story of Sinatra’s inspiration by Crosby has been told in all the biographies: how he would sing along with the records, and how one night in 1935 he took his best girl, a dark-haired beauty named Nancy Barbato, to the Loew’s Journal Square theater in Newark to see Crosby in a live appearance. On the way home he said to her, “Someday, that’s gonna be me up there.”

Nancy Barbato, the seventeen-year-old daughter of a plastering contractor, was skeptical; on an average Saturday night that year, about a million young American males must have been saying roughly the same thing. But Frank Sinatra had begun to believe in his own possibilities. This was America, wasn’t it? And in America anything was possible. So he watched Crosby and listened to him, simultaneously opening himself to other kinds of music too. Crosby’s stardom obviously inspired Sinatra, but in the deepest, most substantial ways, his musicianship did not (the truest heirs to the Crosby singing style were Perry Como and Dean Martin). The most important and enduring influence on the young Frank Sinatra was swing music.

Beginning with Benny Goodman’s breakout in the mid-1930s, and steadily gathering force, this jazz-inspired big band music was soon cutting across all racial and ethnic lines, becoming the music of the generation dominated by the children of immigrants. The growth of radio as a national medium accelerated this process: white kids could hear Count Basie or Duke Ellington; black kids could listen to Goodman (who included black musicians Lionel Hampton and Teddy Wilson in the band); kids of all ethnic backgrounds, including Japanese and Mexican Americans, formed their own swing bands. So although Sinatra was not directly influenced by jazz, he did become the most enduring singer to emerge from the era of the big bands, which could not have existed without jazz. Their powerful, driving, confident sound was emerging at the same time that Sinatra began to sing for audiences.

“I used to sing in social clubs and things like that,” he told the British writer Robin Douglas-Home in 1961. “We had a small group. But it was when I left home for New York that I started singing serious. I was seventeen then, and I went around New York singing with little groups in roadhouses. The word would get around that there was a kid in the neighborhood who could sing. Many’s the time I worked all night for nothing. Or maybe I’d sing for a sandwich or cigarettes — all night for three packs. But I worked on one basic theory — stay active, get as much practice as you can.”

The family resisted. Marty was furious when Frank dropped out of high school in his senior year. He predicted that his son would be a bum. Dolly once threw a shoe at him in his room, expressing contempt for his dreamy ambitions; the shoe hit a photograph of Bing Crosby. Such reactions were not unique to the Sinatra family; many immigrant Catholic families discouraged the artistic ambitions of their children, for decent reasons: they did not want them to be disappointed and hurt. It was safer to take the cop’s test or acquire a real trade. Among the Irish, we called this the Green Ceiling; it was enforced by the question, Who do you think you are?

When it was clear that her son was serious, Dolly gave in, paying $65 to get him a sound system that included a microphone. This was the equivalent of buying a trumpet for Miles Davis. Frank Sinatra had his instrument at last. Almost immediately, the gear made it easier for him to find places to play: amateur contests, bars, high school graduations. The Sinatra legend includes the tale of the formation of the Hoboken Four, winning first prize in 1935 on a popular radio show called Major Bowes’ Original Amateur Hour. The winning group went off together on a Major Bowes tour. For the first time, Sinatra was being paid to sing. He and the rest of the group cut up $75 a week.

“We had turned pro,” he said later. “Bowes was the cheapest son of a bitch in America, and a lowlife besides, but we were singing for money.”

With Major Bowes in command, the Hoboken Four traveled all the way to California, an enormous journey for kids whose world until then had been limited to Atlantic City to the south, New York across the water, and the towns and roads of northern New Jersey. Frank Sinatra was seeing America, which until then was something he had only read about or had seen in the movies. And he was hearing swing bands on the radios in every town.

“A lot of it was crummy hotel rooms, buses, and trains,” he said later. “But still, you saw how goddamned big the country was. And you could hear the same music everywhere. Bing, of course. But also Benny Goodman, Tommy Dorsey. You heard them more than you ever heard the national anthem. They were America.”

The Hoboken Four did not survive the journey; they broke up soon after their return. But Frank Sinatra kept moving, working part-time as a plasterer (for Nancy’s father), unloading crates of books for a wholesaler, catching rivets in a shipyard, ending up in 1937 as a singing waiter in a place called the Rustic Cabin in Englewood, directly across the Hudson River from midtown Manhattan. The pay was $15 a week, plus tips, but the newly completed George Washington Bridge led right over the river to Manhattan, the city of dreams.

The management could not afford a big band to play the music the rest of America was hearing. But Frank Sinatra was singing. Those who later claimed to have seen him at the Rustic Cabin could fill Yankee Stadium. But one who did see him was the trumpet player Harry James, who had just formed his own swing band after leaving Benny Goodman. He needed a boy singer. James heard Sinatra singing on one of the many radio shows that used him, unsponsored programs for which the singer was not paid (or, received 75 cents a performance). He decided to drive over to the Rustic Cabin for a look. Among other songs, Sinatra performed his version of “Begin the Beguine,” a big hit for Artie Shaw. James was impressed, explaining later, “I liked Frank’s way of talking a lyric.” He gave Sinatra the job. That was the turning point, and without changing his name to Frankie Satin, the young man was on his way.

A few months earlier, on February 4, 1939, he had celebrated a raise from the Rustic Cabin to $25 a week by marrying Nancy Barbato in Our Lady of Sorrows in Jersey City. They moved into an apartment on Audubon Avenue in the same city. Frank Sinatra would never live in Hoboken again.

Now earning $75 a week, Sinatra took Nancy on the road with the Harry James orchestra. Every night he would hear James play “You Made Me Love You,” his big hit with Goodman. Every night he would listen to swing music that ripped and roared, a rallying music in a bad time, and then ask questions of the musicians. How did that sound happen? On this record, what is this instrument? He was acquiring theory and practice.

The young musicians in the James band traveled all over the country, doing one-night stands, eating poorly, sleeping on buses, sometimes even returning to New York for gigs at Roseland. By all accounts, Frank Sinatra was a happy young man. He had found the family he was looking for, with his wife at the center. It was a family of men bound together by music, with ambitions far beyond the narrow goals of the streets of Hoboken. Nobody in this itinerant family dreamed of gaining lifetime employment in a shipyard or joining a New Jersey fire department.

“With Harry, for the first time in my life I was with people who thought the sky was the limit,” he said to me later. “They thought they could go to the top, and that’s what they aimed for. They didn’t all make it, but what the hell. They knew the only direction was up.”

On July 13, 1939, he went into a recording studio for the first time and made two recordings with the James band: “From the Bottom of My Heart” and “Melancholy Mood.” A month later he recorded “My Buddy” and “It’s Funny to Everyone but Me.” Then in September he recorded “Here Comes the Night” and a song by Jack Lawrence and Arthur Altman called “All or Nothing at All.” The first release of the last song sold 8,000 copies. A few years later, after he was established as a star, it would be re-released during a musicians’ strike and sell a million. On the earliest recorded vocals with the James band, Sinatra sounds uncertain, unformed, but he does have a distinctive voice. It is certainly not another imitation of Crosby. But on each succeeding date, he gets closer to what he will become, expressing the feeling of loneliness in a new way, within the context of a modern swing band. Those earliest records are like talented first drafts of a good first novel.

Near the end of the year, after only six months with James, Sinatra got an even bigger break: Tommy Dorsey came calling. The Dorsey orchestra was considered the smartest, toughest, hippest of the white swing bands. Some made the same case for Goodman, of course, calling him the King of Swing, but the argument for the Dorsey band was based on its flexibility. Both could do pulsing, vibrant, riff-driven swing pieces; Dorsey could also handle smooth ballads, which Goodman did not do well. (Most musicians of the era thought that the Glenn Miller sound was safe, mechanical, corny.) Dorsey was himself a fine trombone player, in a sweet legato style; he employed first-rate arrangers, such as Sy Oliver (from the Jimmie Lunceford band), Axel Stordahl, Bill Fine-gan, and Paul Weston, and superb musicians, including the trumpet player Bunny Berigan, whose talent was legendary but who would soon be destroyed by alcohol. Sinatra had inadvertently auditioned for Dorsey several years before he landed the job with Harry James. He showed up to audition for a swing band led by a man named Bob Chester. He later told Douglas-Home what followed:

“I had the words on the paper there in front of me and was just going to sing when the door opened and someone near me said, ‘Hey, that’s Tommy Dorsey!’ He was like a god, you know. We were all in awe of him in the music business. Anyway, I just cut out completely — dead. The words were there in front of me, but I could only mouth air. Not a sound came out. It was terrible.”

Sinatra didn’t get the job with Bob Chester. But near the end of 1939 Tommy Dorsey’s star vocalist, Jack Leonard, quit after a dispute, went off on his own, did poorly, and was eventually drafted. The war in Europe was already four months old, tensions were increasing in the western Pacific, and the United States was getting ready for its own inevitable entry into the war, twenty years after young Frank Sinatra saw those triumphant victory parades in Hoboken. Dorsey had heard the Harry James records (Jack Leonard, in fact, had played “All or Nothing at All” for him) and sent for Sinatra.

“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.

Finally, after giving a year’s notice, he broke free from Tommy Dorsey in the fall of 1942. He further infuriated Dorsey by persuading arranger Axel Stordahl to go with him, at a salary of $650 a week, four times what Dorsey was paying him. The departure was bitter. Dorsey was quick to fire people; he could never forgive people who, in effect, fired him. Before granting him a release, Dorsey coldly insisted that Sinatra sign a document awarding Dorsey a third of Sinatra’s earnings for the next ten years, plus an additional 10 percent to Dorsey’s manager. For doing nothing, except letting him go. So much for father figures. By this point, Sinatra was desperate. He signed. He was on his own at last. At first, it wasn’t all that easy. Bookers still were more interested in the big swing bands than in solo singers. They didn’t fully realize that Sinatra’s recordings, played at home, on the radio, or on jukeboxes, were building him a very special audience.

After an impressive engagement at the Mosque Theater in Newark, he was booked into the Paramount as a special added attraction with the Benny Goodman band. This wasn’t Goodman’s idea; he already featured Peggy Lee as vocalist and Jess Stacy on piano. He and his band were the stars, and Sinatra was only a kind of dessert when Goodman’s show was over. But Sinatra wanted desperately to play the Paramount as a solo act, and his instincts were correct. The date was December 30, 1942. He walked out, his suit baggy on his bony frame, more than a little scared, wearing a bow tie that Nancy had made a size larger to hide his Adam’s apple. He started singing, “The bells are ringing, for me and my gal. …” The rest of the words were lost in the screaming.