Why Sinatra Matters

  “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 b
iographies: 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.