by Shawn Levy
But she was a woman and it was the 1910s—and an Italian neighborhood at that—and so she had to find a husband, and she settled on a handsome, illiterate kid from the neighborhood, a guy who couldn’t hold a steady job but cut a dashing figure in the boxing ring. Dolly’s brothers were boxers, which was probably how she came to meet Marty O’Brien, a stout, quiet little guy with tattoos on his arms. Maybe she first took him for Irish, which would’ve appealed to her social-climbing instincts; soon enough, she learned he wasn’t an O’Brien but a Sinatra, but that didn’t make him any less attractive. He might’ve been an unfinished project, but Dolly was sure she could make something of him. Despite her parents’ fears of a layabout Sicilian for a son-in-law, they eloped and married in a civil ceremony. A year and a half later, she bore their first and only child.
Later on, he would try to depict himself as some kind of Dead End Kid turned good, but the truth was that Frank was always plushly seen to. In a neighborhood where the men worked menial jobs and the women raised broods of five, eight, ten brats, only-child Frank had two working parents and a surfeit of candy, toys, bikes, clothes. The homes in which he grew up were the finest to which Italians in Hoboken could aspire. A lot of the Sinatras’ neighbors on the tony streets on which they lived didn’t even know they were Italian: Marty ran a popular speakeasy under his boxing name, and Dolly routinely introduced herself as Mrs. O’Brien; when Frank’s buddies wanted to tease him about his Little Lord Fauntleroy wardrobe—he had his own charge account at Geismer’s department store—-they dubbed him Slacksey O’Brien. They were a family on the rise; a local newspaper society page reported on a New Year’s Eve party Dolly threw after they bought a grand home at the height of the Depression.
By then, Frank had revealed himself as a perfect mix of his parents’ temperaments. Hotheaded and ambitious on the one hand, he liked to loaf and schmooze and was an indifferent student on the other. For all that he inherited from his parents, he was, typically, embarrassed by them as well. Marty was no world-beater, everybody knew that, and he seemed pronouncedly meek even among his friends and colleagues; Dolly was outrageous, flamboyant, earthy, loud, an unignorable commotion whose affectations and ambitions grated on as many people as they inspired. Worse yet, she was the neighborhood abortionist, known to all the Italian girls as the person to turn to when they were in trouble; Frank’s ears would turn red whenever he heard people talk about his mother the “rabbit catcher.” Like everyone else, he was attracted to Dolly’s exuberance, but like Marty and the other men in the family, he feared her. “She was a pisser,” he’d say later, “but she scared the shit outta me. Never knew what she’d hate that I’d do.”
As if to erase the shame Dolly put him through—the dudish threads, the mortifying secret work, the rowdy spectacle she made of herself on nights out with the girls—Frank seemed, at first, to take after Marty. He dropped out of school; he couldn’t keep even a menial job; and he took up a fancy even less promising than Marty’s boxing: Smitten with Bing Crosby, he wanted to be a singer.
At the sight of her boy sporting a yachting cap and crooning in a mirror, Dolly was, as her parents had been by Marty, disgusted, but the idea of denying her boy something that he wanted was worse. She bought him a spiffy electric P.A. system and convinced acquaintances to let him sing in their saloons and restaurants; eventually, she used her clout to get him a job chauffeuring a rising local trio, the Three Flashes, who were preparing to make a few movie shorts for Major Bowes, the era’s great promoter of amateur showbiz talent; with his mom’s backing, Frank quickly rose from driver to jester to full-fledged singer in the group.
The older guys in the act, which Bowes redubbed the Hoboken Four, didn’t care much for the mama’s boy in the midst, even less so when Frank’s singing improved and his solos became a centerpiece of the show. During a several-month nationwide tour as part of one of Bowes’s traveling road shows, they began picking on the skinny kid, beating him up when they felt he needed to be taken down a peg. Frank quit and returned to Hoboken—where Dolly had salted the press with news of his successes.
Three years of scattered, aimless work followed, then a steady job—singing waiter at the Rustic Cabin in Englewood Cliffs, a roadhouse which had a broadcast wire to New York’s powerful WNEW radio station. In June 1939, bandleader Harry James heard Frank on the radio and drove out to see whose voice that was. Shazam: Frank was in. James signed him, they hit the road and cut some records, and Frank got a little bit of notice. In December, Tommy Dorsey auditioned him and he left James with a handclasp and best wishes.
This wasn’t just the call of Lady Luck or the reward of sheer ambition. Somewhere sometime in there, a miracle bloomed. Frank’s voice went from pleasant to stunning: a beautiful, tender instrument possessed of uncanny rhythmic sense and breath control, one of the great talents of the century, a gift no more explicable than those of Joyce and Picasso, recognizable as such even in its juvenile state. Everyone who heard him for the first time was staggered.
As a member of the Dorsey orchestra, Frank became famous: hit records, magazine covers, appearances in movies, flattering press. Like he’d learned from Dolly, he milked it, aggressively courting the press, disc jockeys, anyone he thought could boost his career. He spent more than he earned on his wardrobe alone (he was so finicky about his personal cleanliness that his bandmates with Dorsey nicknamed him Lady Macbeth). Within three years, he was convinced that Dorsey was holding him back from a career that would rival Crosby’s, and he left—after months of bitter, petty infighting, a lucrative settlement, and a grudging goodbye.
Suddenly, everything: Frank signed to play the Paramount Theater in Times Square as an “extra added attraction” with the popular Benny Goodman orchestra; when Goodman introduced Frank, the response from the packed theater was so volcanic that he asked his band, “What the fuck was that?” Within a few months, the whole world would know. Spontaneously, Frank had become the beloved of a generation of wild-eyed fans—young girls, mostly—who made him a teen idol decades before anyone ever thought to manufacture such a thing.
Boosted by the devilishly clever press agent George Evans, Frank became bigger than Crosby or Vallee or Caruso—the biggest thing ever in showbiz, in fact. There was a core of critics and musicians among the cognoscenti who admired his artistry (James Agee spoke fondly of his “weird, fleeting resemblances to Lincoln”), but the wellspring was the kids—the bobby-soxers, as they were named for an affectation of footwear. Sinatratics they called themselves, forming cultish cells in devotion to their new god: the Slaves of Sinatra, the Sighing Society of Sinatra Swooners, the Flatbush Girls Who Would Lay Down Their Lives for Frank Sinatra, the Frank Sinatra Fan and Mahjong Club.
These daughters of flappers were quick to connect the longing in Frank’s voice with their own longings, his quavery presence with the absent boys who were off fighting the Hun and the Nip (Frank was 4-F: punctured eardrum). Odd as it may have seemed to everyone in the business, the wiseass runt with the heavenly voice was some kind of sex symbol. (And he’d always be one: For a half-century, Frank was one of the ways America made love, quite often the most popular; he was able to get away with anything because he hit people in their most personal spots.)
By the late fifties, by Rat Pack time, when his audience had grown up, Frank could be as sexy as he felt, but in the first blush of his fame, he had, like all teen idols, to be officially Off Limits. Conveniently, he had a cozy domestic life to play up: He’d been married to a girl-next-door type since 1939; by 1944, they had two kids, one named after each of them: Little Nancy and Frankie Jr.
For George Evans—and for Frank’s many important employers: Columbia Records, CBS radio, MGM, Lucky Strike—this was a perfect setup: a talented, massively popular young guy with a solid family and a wholesome aspect. But Frank seemed hell-bent on screwing it up. There was that entourage—big, unlikely guys, boxing writers, gamblers, songwriters buttering him up—and there were women and there was this habit of snapping
back at the press and there was all the politics: Bad enough he was 4-F; did he have to sing “Ol’ Man River” and break bread with Eleanor Roosevelt? Evans spent the better part of the forties covering Frank’s ass, cozying up to some columnists and scratching and clawing at others while his client carried on however he pleased, simply assuming that somebody else would sweep it up.
He rose to insane heights. In 1939, he was waiting tables at the Rustic Cabin for $15 a week; by the end of the war, he was a bigger star in more media than anyone in the world and had grossed an estimated $11 million. By sheer earnings standards, he was probably the biggest star ever, anywhere; it almost didn’t matter that he was an artistic genius with more pure vocal talent than virtually anyone who’d ever been recorded.
Still and all, he was a creature of the popular culture and, as such, subject to the public’s whimsies. As the forties closed, talk leaked into the press about ties to communism and mobsters, there were ugly spats with writers, photographers, waiters, carhops, fans. His once-promising film career had sputtered—The Kissing Bandit, anyone?—and, after Frank made a wisecrack about one of Louis B. Mayer’s mistresses, MGM gave him his release. On the radio, he was bumped down from Your Hit Parade to a fifteen-minute, B-level show; on TV, CBS just plain dumped him.
He had trouble with his voice—he opened his mouth once at the Copa and couldn’t make a sound come out—and he seemed, further, to have lost his aesthetic way, letting Columbia’s new A&R man, Mitch Miller, talk him into making horseshit records with arrangements scaled wrong for his voice and dog barks thrown in as comic relief. The pathetic fall seemed poetically complete in 1952 when he returned to the Paramount Theater in support of a film of his own (the forgettable Meet Danny Wilson) and couldn’t even fill the balcony, much less stop traffic in Times Square.
Frank had gone from “extra added attraction” to King of the Universe in a couple of years; then, in about the same time span, he couldn’t get a job—and not a few people in the business were glad of it. With his ambition, quick temper, and iconoclasm, he’d done a lot of pissing off in his decade on the scene. His reputation was poison: When Capitol Records president Alan Livingston told his staff that he’d signed Sinatra at terms very favorable to the company, they groaned as one.
Presaging all of this calamity, turning the bobby-soxers against him and making him look like some pathetic pussy-whipped Milquetoast, was his wanton affair with Ava Gardner. Frank had never been faithful to Nancy in even a loose sense of the word, but, like many showbiz wives, she seemed willing to put up with peccadilloes even with such hot numbers as Marilyn Maxwell and Lana Turner. But this thing with Ava was more passionate and public than any of his other dalliances; it might have begun as a meaningless Hollywood fling, but they carried on all over the country throughout 1949, and Frank’s cardboard marriage finally became untenable. In the spring of 1950, he left the pretty Italian girl and the three cute kids that were his P.R. chastity belt. George Evans, enervated and skinny to begin with, bald from defending him, up and died one night after arguing with a columnist about Frank and Ava; he was forty-eight, and his heart had given out.
The affair and subsequent marriage were absurdly tempestuous and about as private as a presidential campaign; Ava was a lioness and Frank was her plaything. She was as promiscuous, lustful, hard-drinking, and profane as he was, and she had the hooks into him but good. She busted his balls mercilessly, running off with bullfighters and making him look like an ass in front of the world. He threatened suicide several times and took two stabs at it—once in Lake Tahoe with pills, once in New York with a razor. His disgrace and comeuppance were complete: Not only was he a has-been as a singer, an actor, and a performer, he was a flop as a cocksman. He was a joke: last year’s punch line.
When he finally managed to crawl out of his hole, then, it was all the more resoundingly triumphant. He achieved it in part through a movie role—Maggio, the pip-squeak private who died horribly at the hands of a bullying sergeant in From Here to Eternity. Throughout the latter half of 1952, Frank campaigned actively with Columbia Pictures president Harry Cohn to get the part, and Cohn’s relationship with the Chicago Outfit’s West Coast point man, Johnny Rosselli, assured Frank at least a hearing. He got the job, he did really good in it, he got the Oscar, poof: He was all better. Once considered an overweening interloper in Hollywood, he was suddenly in the spring of ’54 a resilient, dues-paying member of the acting club. He had done the good thing; he had died for his fame and resurrected himself. He made more movies and he had hit after hit; he was even good in some of them.
At the same time, he took a new turn musically. No longer was he the reed-thin, warbling young crooner with a voice like a viola and a closet full of floppy bow ties. Now working for Capitol Records, he was more propulsive and dynamic, his voice richer and deeper—a cello. He was wearing fedoras and stylish suits; he was singing up-tempo about swinging and in dramatic, elegiac tempi about loss.
As in the movies, he seemed to have earned the right to his station; what’s more, as a singer, he expanded the very art form. He cut whole albums of songs built on the same musical ideas—saloon songs, swing numbers, waltzes—and even lyrical ideas: flying, dancing, the moon. Through the decade, he made the greatest pop records in history—one after another, sometimes as many as four a year.
Come 1959, he could look back twenty years and see a punk kid with nothing but ambition to his credit, he could look back a decade and see a big star dumped by the world, or he could look into the mirror and see the most influential and talented popular entertainer of the century.
Now what?
Frank was to become such a colossus of American popular culture that it would’ve been crazy in his heyday to think of him as needy. But his heroic Last Honest Man posture always had as a counterpart a little boy’s thirst for camaraderie and love. “I don’t think Frank’s an adult emotionally,” his friend Humphrey Bogart sniffed. Shirley MacLaine was more clinical, calling Sinatra “a perpetual performing child who wants to please the mother audience.”
Never mind all the gruff stuff offstage: The evidence of what was in his heart was in his art. Here was a man who lived amid an entourage that could expand, if he wished it to, to infinity, a man who had virtually every woman he ever desired, a man for whom no material comfort was unattainable; yet his music was at its richest and most intense when he sang piteously about loneliness. His familiar swinging cockiness would be overwhelmed by a gray, anguished fog hovering over a profound, hollow core—the achy soul of the Tender Tough. “I’ll Be Seeing You,” “These Foolish Things,” “Guess I’ll Hang My Tears out to Dry,” “In the Wee Small Hours,” “Angel Eyes,” “What’s New?,” “One for My Baby”—a world of crushed dreams, blasted hopes, distant, impossible romance. People called it suicide music and couldn’t understand why he slowed down every show to perform it—sometimes exclusively. But loneliness was the most vibrant color in his musical palette, and it obviously came from someplace very deep inside of him.
Indeed, he was born to it. He was, of course, an only child—try to name another Italo-American only child of his generation!—and grew up with a yearning for the companionship that his friends, neighbors, and cousins all enjoyed in their homes. The cash and clothing that his mother lavished on him were his first means of acquiring a society: He handed down suits to kids whose friendship he courted; he bought burgers and candy and comic books, cultivating early on a habit of “gifting”—treating the house to drinks or meals or clothes or women or more. The assets Dolly spotted him as a teenager—his wardrobe, his car, his sheet music arrangements, his portable sound system—they were a way for him to get a leg up in show business, true, but they were also a means of being part of a bigger group.
Which is what made it so perfect that Sinatra came into his own as a performer during the big band era, when a singer was by necessity a piece of a large, vibrant whole. The Harry James and Tommy Dorsey bands were like big clubs of chums for him—and he di
dn’t have to buy his way in, either. He gorged himself on the grand bonhomie that the bands instantly provided him—the card games, hazing, drinking, dreaming, and bonding that he and his fellow musicians engaged in during endless bus rides. He was like a congenital junkie who became addicted with his very first hit. As soon as he’d begun life in that dazzling musical fraternity, he wanted to live no other way.
Witness his recollection of the day on which he left James for Dorsey: January 1940, Buffalo; the James band was headed to Hartford; Frank would briefly visit New York, then join Dorsey in Rockford, Illinois; it was the single big break of his career, and he’d yearned for it and schemed to make it so; still, he struggled through the separation from his bandmates of a mere six months: “The bus pulled out with the rest of the boys at about half-past midnight. I’d said good-bye 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.” (This was, keep in mind, a married man with a child on the way.)
Of course, the Dorsey band was to offer Frank the same sort of companionship he enjoyed with James. Moreover, Dorsey himself would come to serve as a hero and model for his young singer; Frank dressed and spoke like him, he studied his famous breathing technique, he even took up his hobby of model railroading. Still, even with the prospect of a new gang of buddies assured him, he arrived in Illinois with the beginnings of his own coterie, a safeguard against ever finding himself staring longingly at the receding taillights of a bus again: Nick Sevano, a Hoboken haberdasher who dressed him, did his errands, and even lived with him and his family when they weren’t on the road, and Hank Sanicola, accompanist, business manager, and, as his girth suggested, sometime thumbbreaker.
