Sinatra was seventeen when he left home, he said, which would date his departure to sometime in 1933. Two years would pass before he got a significant break, more than five before he really broke into the music business. “They call me an overnight success,” he would say then. “Don’t make me laugh!”
What followed is something of a lost period. It has proved impossible to identify any specific events between 1933 and the fall of 1935— surprising in an otherwise well-chronicled life. There are, however, a few clues. Dolly softened and gave Frank $65—a princely sum then—to buy a rudimentary sound system. It was a new device, much coveted by musicians, that gave him an entrée to aspiring bands. It was comprised of an amplifier, a speaker and, crucially, a microphone.
Up to that time, the only way singers could boost their voices had been by using a megaphone. Rudy Vallee used one and, a contemporary recalled, Frank had been toting one around “like it was part of his wardrobe.” The megaphone brought humiliation. “Guys would throw pennies into it to see if they could get me to swallow them,” he recalled. “Lots of fun.” Bing Crosby, by contrast, had started using early-model microphones as soon as they became available in the late 1920s. Suddenly, performers with financial resources no longer had to project their voices. Some saw the microphone as a sort of deception. Not Sinatra.
“I discovered very early,” he was to say, “that my instrument wasn’t my voice. It was the microphone.” One reporter in the early days wrote of Sinatra’s hands “tightly gripping the microphone, as if to sustain a body too frail to stand alone.” One night years later in Las Vegas, when he found his mike was dead, he simply dropped it on the floor and left the stage. He was not prepared to work without his secret weapon, because it made “speech-level singing” possible. It gave Sinatra intimacy with the audience.
Unlike many performers who have followed him, Sinatra sought to use the microphone “with great economy.” “I usually try to have a black one,” he said, “so that it will melt into my dinner-jacket and the audience isn’t aware of it.” With a microphone, he said, “you can sing as if you’re singing in someone’s ear, you can talk to a buddy at the bar, you can whisper sweet nothings to a woman.”
This last, of course, above all. “To Sinatra,” E. B. White thought, “a microphone is as real as a girl waiting to be kissed.” Or as Gore Vidal put it: “Sinatra got the blood flowing. Bing Crosby put you to sleep.”
In New York after his father sent him packing, though, there were more urgent priorities. He had a room to pay for, and he needed to eat. “I went around,” he recalled, “singing with little groups. . . . Many’s the time I worked all night for nothing. Or maybe I’d work for a sandwich and cigarettes—all night for three packets.”
He had first come to the big city as a wide-eyed eleven-year-old, brought in by his parents to see the Christmas display at Macy’s. More recently there had been sneak trips with school pals, to see the wonder of bare-breasted women at the burlesque houses. Now, at seventeen, he began hanging out at Roseland Ballroom to hear the big bands. Most important of all, he sampled the club scene.
A musicians’ Shangri-la was coming into its own in New York at that very time on the Midtown block between Fifth and Sixth Avenues, remembered now as “Swing Alley,” “The Street That Never Slept”— and as plain “52nd Street.” The block was fast becoming the place to be for night people, actors, writers, and politicians, and the gossip columnists who fed on their activities. Above all, it was the home of jazz.
Bing Crosby had started as an obscure jazz singer, and jazz gave Sinatra his sense of rhythm and his lifelong readiness to improvise. Fifty-second Street was where the culture of Harlem met the white world, and Sinatra gave credit to more than a dozen black “jazzmen whose art helped to educate me musically.” “Talent has a blindness to color,” said Sinatra, and he championed racial equality when it was still controversial to do so. Billie Holiday, “Lady Day,” was not yet performing regularly on the Street in 1933, but did appear occasionally. When he first heard her sing “standing under a spotlight in a 52nd Street jazz spot, swaying with the beat,” said Sinatra, “I was dazzled by her.”
A quarter of a century later, he offered the ultimate accolade. “Billie Holiday was and still remains the greatest single musical influence on me. . . . The depth of Lady’s singing has always rocked me.” It was from her, he said, that he learned “shading, phrasing, dark tones, light tones, and bending notes.” Holiday, he thought, “lived inside the song.” In time the admiration became mutual. Holiday would one day say she wished she could sound like a female Sinatra, and on her last album paid him the tribute of singing “I’m a Fool to Want You,” which he had made famous.
Many of the big names of the big band era, with whom Sinatra would eventually achieve national prominence, were familiar figures on 52nd Street. Benny Goodman was a regular at the Onyx Club, playing his clarinet. So was Tommy Dorsey, jamming on trumpet—surprisingly not on the trombone for which he is famous.
The Street had been home to more speakeasies than anywhere in the city during Prohibition, which was about to end in 1933. Prostitution was a feature in the area. Frank was among night people, who thought nothing of staying up till dawn. Among them were top gangsters, who had owned and frequented the speakeasies and dominated the clubs and restaurants that replaced them once drinking became legal again. They were also increasing their penetration of the entertainment industry.
Four powerful mobsters in particular frequented the nightspots of the New York area: Lucky Luciano, by now the de facto head of the national crime syndicate; his close friend Frank Costello of New York; Costello’s cousin, New Jersey crime boss Willie Moretti; and Dutch Schultz, who owned a 52nd Street club, Club Abbey, until his murder by one of Luciano’s henchmen. All figure in the Sinatra story.
FRANK RECALLED HIS EARLY ADVENTURES in New York City as having had “a kind of motion picture ending.” “On Christmas Eve,” he said, “I went home to visit my folks and there was hugging and kissing and making up.” This was probably in December 1933, the month he turned eighteen. Marty was relieved to have his only son home, and Dolly had become his enthusiastic backer. Armed with more money from his parents, Frank started acquiring the sheet music for a wide selection of popular tunes. This gave him even more leverage with local bands, and he began to get more gigs.
At an amateur contest at the New York Academy of Music, he experienced the stage fright that unbeknownst to audiences would dog him far into the future. “I swear on my mother’s soul,” Sinatra would say on The Larry King Show in 1988, “I tremble every time I take the step and walk out onto the stage.” At the Academy, as he waited in the wings, Frank could hear other competitors being subjected to catcalls and shouts of “Get the hook!”—the curved pole used to yank hopeless performers off the stage. “I’m standing there shaking,” Sinatra remembered, “figuring that the moment they announce a guy from Hoboken, he’s dead.”
The audience did not sentence Frank to the hook, but nor did he win a prize. Closer to home, in a contest at the State Theater in Jersey City, he sang “That Old Black Magic” and did win a prize. He broke into radio in a modest way, too, when a contact of his uncle Dominick got him onto WAAT in Jersey City. Frank sang without pay, but any exposure helped. An old radio guide shows that he had a fifteen-minute slot in April 1935, under his own name. On other occasions, by one account, he was identified only as “The Romancer.”
The next break came thanks to some young musicians who had been customers at the Sinatras’ bar. Members of a trio called the Three Flashes had been hired to sing weekends at the Rustic Cabin, a roadhouse on Route 9W, fifteen miles outside Hoboken. “Frank hung around us like we were gods or something,” according to Fred Tamburro, one of the Flashes. “We took him along for one simple reason: Frankie-boy had a car. He used to chauffeur us around.”
“Then,” Tamburro’s widow said, “Dolly went over to speak to Freddie and asked him to put Sinatra in the group.” “His mot
her started pestering us,” said Flashes’ musician Jimmy “Skelly” Petrozelli. “Dolly was a big wheel in Hoboken. She kept throwing her weight around, and we finally took him.” “She pushed and pushed Frankie and got him in,” Dolly’s niece Rose said recently. “There wasn’t anybody who didn’t know who she was. She knew all the gangsters, and all the politicians.”
Dolly got her son into the Three Flashes just as they were about to try out for a radio show hosted by a popular impresario, Major Bowes. When Frank tagged along to the Bronx, for a first meeting with Bowes, Tamburro explained that they were now four. Bowes liked what he heard. He was swayed, according to Tamburro, by the group’s rendering of “Shine”—“Shine away your bluesies”—to which Frank contributed some solo lines. Sinatra said it was his rendering of “Night and Day” that won Bowes over.
A few days later, in a competition at New York’s Capitol Theater, they were introduced as the Hoboken Four, “singing and dancing fools.” Fools, Bowes said, “because they’re so happy.” The audience applause meter, and call-ins by radio listeners, won them first prize— a six-month contract to perform on stage and radio around the country. It was September 8, 1935, a few months short of Frank’s twentieth birthday.
The Bowes tour turned out to be more grueling than glamorous, and ended in bitterness. The boys’ pay of $75 a week each ($1,000 today) was more than any of them had earned before, yet that seemingly munificent sum shrank when they found they had to pay their own living expenses. They were shunted by train and bus across thirty-nine states and beyond: to cities including Des Moines, Wichita, Los Angeles, San Diego, San Francisco, Oakland, Vancouver, then back down to Bellingham, Washington.
It became obvious during the trip that Frank had a special talent. Asked to perform at an Oakland nightclub, he got up and sang solo without rehearsal. “He got so good after just a couple of months on tour,” Petrozelli remembered. “The bus would be packed, people talking, people necking, people reading—everything people do on a bus. Then Frank would start to sing from somewhere down back and everything stopped . . . he had his heart and soul in it. That kid really had it.”
“Frank stood out as the best in the group,” a former Bowes staff member said. “After the show people would flock backstage. . . . The others would be asked to sign an autograph or two, but Frank was practically torn apart. He’d have to fight off the nicest women you’ve ever seen. All the women wanted was to climb into bed with Frank Sinatra.”
In Hoboken, so far as is known, his teenage sex life had been limited to flirtations with neighbors’ daughters and the long-running romance with Nancy Barbato, still just eighteen in 1935 and very much under the wing of her family. On the road, far from home and treated like a mini-celebrity, he was the young stud. According to Tamburro, “He could get all the tail he wanted. This guy had an appetite for sex like no one I ever knew.”
Frank’s popularity, and especially the success with girls, did not go down well with his fellow singers. On occasion they took it out on him with their fists, and one of several fierce brawls ended with Tamburro knocking Frank unconscious. After three months, he quit and went home to New Jersey. The reason, he said later, was that he had “got homesick.” The rest of the group completed the tour but broke up soon afterward. Two took jobs as waiters and Tamburro worked for a while as a car salesman. When Sinatra became famous and Tamburro asked him for a job, Sinatra offered to hire him as a valet. He turned the offer down.
Despite the unhappy ending, Sinatra remembered that first tour as the experience that “made me stick to singing as my lifetime ambition and work.” Two more arid years were to pass before luck again came his way. He remembered this time as a “panic period.” He tried out for a job as a singing waiter at Vaughan Comfort’s restaurant on the Jersey Shore, but was not taken on. The pianist said he did not sing loudly enough. Things improved somewhat after the Sinatra family turned out in force for a Sicilian Cultural League function at Hoboken’s Union Club. Marty and Dolly presented the league with an American flag and Sam Sinatra, the cousin who had frustrated Frank by doing well at school, was treasurer. Frank began getting some work at the club.
It was not enough, though, to make a living. On December 12, 1936, he sang in a “Minstrel Show” sponsored by his father’s fire company at Malec’s Plauderville Ballroom; he was listed on the program as just one of eighteen “Boys” in the chorus. It was his twenty-first birthday.
Frank took to haunting the lobbies of radio stations in New Jersey and New York. “I’d come out of my office,” recalled Jimmy Rich, the staff pianist at WNEW in Manhattan, “and he’d be standing there to see me or anybody who would listen. . . . Somehow he’d get past the receptionist.” He was prepared to sing for bus fare or “for no,” no pay at all.
He performed on that basis on WNEW, WOR in Newark, and again, with a guitarist friend to accompany him, on Jersey City’s WAAT. He especially liked WOR because the station boasted an orchestra with strings. “I had three songs that I did with the string section—I wanted to work with strings,” he said later.
In the spring of 1937, Frank contacted Ray Sinatra, at that time a member of the NBC house orchestra. “He wanted to know whether we might be related,” Ray recalled. “He mentioned that he wanted to be a singer.” Ray checked, found they were cousins of some sort, and helped Frank get a stint on an NBC radio show.
This was a high point in a low time. “The cream cheese and nut sandwiches I ate when I was living on about thirty cents a day, working on those programs!” Sinatra remembered. “The coldest nights I walked three miles because I didn’t have a dime bus fare. . . . But I worked on one basic theory—stay active, get as much practice as you can.”
Staying active meant more trips into Manhattan, often with his Hoboken friend Nick Sevano. On a visit to a Broadway music publisher in search of sheet music, the pair were befriended by a young man named Hank Sanicola. He was a song plugger, one of an army of faceless musicians paid by publishers both to cultivate performers and to get new music played on the radio. Frank was not yet a good bet, but Sanicola took him under his wing.
Soon they were spending hours together, Frank trying out songs as Sanicola banged away on the piano. “Without his encouragement,” Sinatra was to say, “I might very easily have tossed in the sponge.” Sanicola had some musical talent, business savvy, and the physical build of a blacksmith. He recalled becoming Sinatra’s “strong arm . . . I used to step in and hit guys when they started ganging up on him in bars.” Sinatra later employed Sanicola as his manager and Sevano as his general factotum. For now, in the “panic period,” Sanicola helped out by slipping him a little money each week.
Frank also got to know Chester Babcock, a song plugger at Remick Music. Babcock, who was keeping the wolf from the door by working as an elevator operator in a hotel, aspired to a career as a composer. Under the name Jimmy Van Heusen, the last name appropriated from the shirt manufacturer, he would find success sooner than Frank. “Come Fly with Me,” “High Hopes,” “My Kind of Town,” and “Only the Lonely” are just a few of the dozens of songs he was eventually to write for Frank. When the good times arrived, Van Heusen was a natural to become a Sinatra intimate. He managed to combine a lifelong enthusiasm for flying—he later piloted both Sinatra and Bing Crosby—with a gargantuan appetite for sex and strong drink. At twenty, the nucleus of Frank’s friendships was already taking shape.
In the late 1930s, though, these friends were still trying to make it and Frank was what the pluggers called a “kolo,” a wannabe not yet established on a major radio network. He had become something of a 52nd Street regular, attending Sunday afternoon jam sessions at the Hickory House jazz club. He hung around there in a back booth listening to Count Basie, Artie Shaw, Benny Goodman, Art Tatum, and Nat “King” Cole among others, waiting for a chance to sing.
Billie Holiday was appearing on the Street more often now, her trademark gardenia in her hair, bewitching listeners with her songs of love and hurt. When two m
en at the Onyx Club talked loudly during her performance one night, Frank laid into them—one of his earliest public displays of violent temper.
In those formative days, Sinatra said, he also paid close attention to two other black women singers. He felt “touched deep down” by the work of Ethel Waters, celebrated for her recording of “Stormy Weather.” By then in her forties, Waters like Holiday had been reared in poverty, the daughter of a twelve-year-old mother who had been raped by a white man. And in about 1938 he would hear the British-born Mabel Mercer, just arrived from cabaret work in Paris. “He would be there almost every night,” Mercer’s press agent Eddie Jaffe remembered. “He would tell everybody how influenced he was by the way she sold the lyric.”
People in the business, meanwhile, were telling Frank he could learn from opera. He was spending more and more time at Nancy’s home, where opera was played all the time. He fantasized about singing the aria “Vesti la giubba”—“On with the Show”—from I Pagliacci, and envied those with the voice to do so. He thought his contemporary Robert Merrill “the greatest baritone I ever heard.” If reincarnation were possible, Sinatra would one day say, he would like to return as Luciano Pavarotti. Both great singers would one day become his friends.
SOMETIME AFTER the Hoboken Four broke up, probably in 1936, the group’s former leader, Fred Tamburro, noticed a change in Frank. “He didn’t talk Hoboken anymore. He sounded like some Englishman or something. I asked him about it, and he told me he took lessons from some professor.” At Sanicola’s suggestion, Frank was seeing a voice coach. “His voice then was very thin,” Nick Sevano recalled. “It didn’t have range. We went to see a coach twice a week. He’d have him go through the scales on the piano. And then Frank would study at home, a couple hours a day, and learn rhythm and timing.”
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