What is it about Frank Sinatra that no one else can touch? He could swing, break hearts, and behave badly, and he made his voice an instrument that kept reinventing American music.

FrankSinatra4To get to the bustle of Manhattan from Hoboken, New Jersey, which is just across the Hudson River, takes about fifteen minutes by ferry; to forget the deadliness of the place has taken Frank Sinatra most of his lifetime. Sinatra was born in Hoboken, on December 12, 1915. In those days, from River Road, now called Sinatra Drive, you could see New York’s crenellated skyline, rising like a bar graph of profits, and, if you walked to the dock’s edge, the ass end of the Statue of Liberty. The vista was at once a thrill and a rebuke. As an adult, Sinatra often referred to his home town as a “sewer”; after 1947, when he was given the key to the city, he didn’t return to it officially until 1985, when he received an honorary degree from Stevens Institute of Technology, an engineering school that his ambitious mother had wanted him to attend. Dolly Sinatra, who had an immigrant’s faith in success, wanted her school-shy son to become some kind of powerful man. In time, of course, Sinatra seized more than power; he infiltrated the Western world’s dream life. He is “the most imitated, most listened to, most recognized voice of the second half of the twentieth century,” the New York disk jockey William B. Williams said in the fifties, tagging him forever with the epithet Chairman of the Board. Sinatra, whose tape-recorded voice was heard by the Apollo 12 astronauts as they orbited the moon, and whose two hundred and six CDs currently in print make him the most comprehensively digitally preserved music-maker in the history of recorded sound, refers to himself as the Top Wop. Even the Secret Service, which protected him when he produced Presidential inaugurals for both John F. Kennedy and Ronald Reagan and whenever he lunched with Nancy Reagan at the White House, spotted the sense of manifest destiny in Sinatra. Its code name for him was Napoleon.
Sinatra’s life has been one long show of mastery over his Hoboken years, whose scars are harder to see than those on his neck, ear, and cheek from an agonizing forceps delivery that yanked the nearly thirteen-pound baby out of his twenty-one-year-old mother’s diminutive body and prevented her from having other children. “His bravado, his bigness, the size of him in public life—it’s part of him. But underneath there is something quite—I don’t want to say ‘sensitive,’ because that’s an understatement—underneath there is a delicate, fragile boy,” his daughter Tina Sinatra told me recently. When he was a young man, Sinatra’s expectations were woefully at odds with his abilities. He wanted to build bridges, but he’d spent only forty-seven fractious days in high school; he wanted to be a sportswriter, but he was a “deez, demz, and doz” guy; he loved music, but he couldn’t read it, and was too impatient to learn an instrument. “The story of Sinatra, of me, of all kinds of people of our time is that they had to cross the bridge either from Jersey or from Brooklyn to Manhattan and have people say ‘You fit,’” the writer Pete Hamill says. (Hamill is the son of Irish immigrants, and a high-school dropout, whom Sinatra once approached to write his biography.) He adds, “You went there to sort of say, ‘Hey, this is mine, too.’”
As a solitary latchkey kid, Sinatra would often wander down to the Hoboken wharves, dangle his feet over the docks, and stare at the cityscape, trying to imagine a future. “He didn’t dream,” Tina Sinatra insists, of her father’s often repeated account of those days. “He said, ‘I’m gonna do it. I’m gonna get across this river. I’m gonna go there and make a name for myself.’” At Sinatra’s back—far from the river, in the shadow of the New Jersey Palisades—were the working-class warrens that first-generation Italians like his parents were trying furiously to climb out of. Hoboken had large Irish and German populations; Italians were at the bottom of the pecking order. As a young man, Sinatra’s father, Marty, boxed as a bantamweight under the name Marty O’Brien, in order to be allowed to compete. Dolly, who had strawberry-blond hair and blue eyes, sometimes passed herself off as Mrs. O’Brien, and when they opened a bar, during Prohibition, they called it Marty O’Brien’s Bar.
Books have been written about Frank Sinatra’s women, who were trophies to his success; but his squat, bespectacled mother—the outspoken daughter of a well-educated lithographer who had brought his family to Hoboken from Genoa—had more to do with his success than any of the countless babes with whom he was associated. Dolly spoke all local dialects of Italian as well as a gamy version of English, and she was a popular local political figure, a Democratic ward boss who could guarantee the Party machine at least five hundred votes at every election. She made things happen for others and for herself. Her son may have lacked for her attention when he was growing up (between the ages of six and twelve he was cared for during the day by his grandmother), but even in the midst of the Depression Dolly made sure that her moody boy had a circle of friends, by providing him with a dapper, plentiful wardrobe, a 1929 Chrysler, and enough spending money to treat his cronies to sodas and movies. Sinatra’s tenacity, drive, and cunning owe a lot to Dolly, who always had her eye on the main chance: in her time, she was both a midwife and an abortionist, a local politician and a Prohibition saloonkeeper. “She was the force!” Sinatra said. “My son is like me,” Dolly said. “You cross him, he never forgets.”
“I think he was partial to his dad,” says Nancy Sinatra, Sr., who was married to Frank throughout the forties and is the mother of Nancy, Tina, and Frank, Jr. Sinatra’s father was a quiet, passive man, while Dolly, a typical Italian balabusta, controlled the Sinatra household and had a stevedore’s heart and mouth. “Son-of-a-bitch bastard” was her most common curse; she called Sinatra’s sidekick, the saloonkeeper Jilly Rizzo, “fuckface” (as she did most everyone else); she nicknamed her youngest granddaughter, Tina, Little Shit. Among her grandchildren, Dolly favored Frank, Jr., whom she could idealize and pamper as she had her own son. “She always said to me and Nancy, ‘When I’m dead, everything goes to Frankie. You girls get nothing,’” Tina Sinatra says. “She was a difficult woman.” Even though Dolly spoiled the child, she didn’t spare the rod. She kept a piece of wood the size of a billy club behind the bar at home. “When I would get out of hand, she would give me a rap with that little club; then she’d hug me to her breast,” Sinatra told Hamill one night in the seventies as they discussed the singer’s erstwhile biography in a Monte Carlo hotel room. Hamill adds, “Then Sinatra said, ‘I married the same woman every time.’ That’s Ava. That’s all the women. He had this mother who punished and hugged him, and they were all part of the same thing.”
From the start, Sinatra embraced and bullied the world as his mother had embraced and bullied him. “All of Dolly’s ambitious energy was thrust into him,” Tina Sinatra says. One episode in Sinatra’s youth bears witness to this. Dolly had prevailed upon her son’s godfather and namesake, Frank Garrick, who was the circulation manager of the Jersey Observer, to get her son a job. Sinatra duly found work on the paper’s delivery truck. When the Observer’s sportswriter died, Dolly got Sinatra to go back to Garrick and ask for the writing job. Sinatra arrived at the paper dressed for reporter’s work, but Garrick was out; undeterred, Frank sat at the dead writer’s empty desk and went through the motions of doing the job. When the editor asked Sinatra who he was, he answered that he was the new sportswriter and that Garrick had sent him. His lie was discovered when Garrick arrived, and his godfather was forced to fire him. “Oh, the temper and the words and the filthy names he called me…. Like he was going to kill me,” Garrick told Kitty Kelley in “His Way,” her unauthorized biography of Sinatra. “He called me every terrible name in the book and then he stormed out. He never said another word to me until fifty years later, after his mother died. She wrote me off, too, and even though we lived in the same town, she never said another word to me for the rest of her life.”
Over the years, Dolly and her son also went through periods of not speaking. “Nancy, our mother, wasn’t good enough,” Tina Sinatra says. “Then, all of a sudden, she was good enough. When Ava was on the horizon, this was against God, how can he do this? But then the press turned in their favor. They became the Romeo and Juliet with his mother keeping them apart. Dolly changed her whole attitude. She always gave Dad a tough time.” There was another Mexican standoff after Sinatra announced his engagement to his fourth and current wife, a former Las Vegas showgirl, Barbara Blakely Marx, whom he married in 1976. “I don’t want no whore coming into this family,” Dolly said. As Sinatra told Shirley MacLaine in her excellent memoir “My Lucky Stars,” “She was a pisser, but she scared the shit outta me. Never knew what she’d hate that I’d do.”
Dolly enjoyed singing, for example, especially at weddings and at political beer parties, but she didn’t want her son to be a singer. The notion had first dawned on Sinatra when he was about eleven and was in his parents’ bar, where there was a player piano in the front room. “Occasionally, one of the men in the bar would pick me up and put me on the piano. I’d sing along with the music on the roll,” Sinatra said in a 1986 lecture he gave at Yale University. “One day, I got a nickel. I said, ‘This is the racket.’ I thought, It’s wonderful to sing…. I never forgot it.” Under pressure to make something of himself, Sinatra increasingly focussed on the one asset he was sure he possessed: his voice. “In my particular neighborhood in New Jersey, when I was a kid, boys became boxers or they worked in factories; and then the remaining group that I went around with were smitten by singing,” Sinatra said during a 1980 radio broadcast. “We had a ukulele player, and we stood on the corners and sang songs.” Sinatra liked to listen to Gene Austin, Rudy Vallee, Bing Crosby, Russ Columbo, and Bob Eberly—but of all of them he idolized Crosby, whose casual sailor’s cap and pipe were props that Sinatra himself would soon adopt. As his ambition to sing grew, so did Dolly’s hectoring. When she saw a photo of Crosby in her son’s room, she threw a shoe at him and called him a “bum.”
But when Dolly realized that she couldn’t break her son’s will she tried to empower it. She chipped in for the orchestrations Sinatra rented to local bands who, as part of the deal, took him along as singer; she bought him portable speakers and a microphone; she used her influence to help him hustle gigs at roadhouses, Democratic Party meetings, and night clubs. In 1935, still unemployed and living at home, Sinatra attached himself to a trio in nearby Englewood called the Three Flashes. “We took him along for one simple reason,” said the trio’s baritone, Fred Tamburro. “Frankie-boy had a car.” When the Three Flashes—all Italian kids looking for a leg up—were asked to do some movie shorts for Major Bowes, whose radio “Amateur Hour” was the most successful show on the air, Sinatra wanted to sing with them; they turned him down. Dolly quickly intervened, and before long the Three Flashes became the Hoboken Four. On September 8, 1935, they appeared on the millionaire Major’s show, singing the Mills Brothers hit “Shine.” Sinatra’s first words in public were at once pushy and playful; they got a laugh. “I’m Frank, Major,” he said. “We’re looking for jobs. How about it?” The Hoboken Four won that night, with forty thousand people calling in—the largest vote up to then in the show’s history.
From that first moment, the public took Sinatra in with an affectionate avidity that he could never call forth from his mother. “She always expected more of him,” Nancy Sinatra, Sr., says. “It was never enough. For her, the cup was always half empty. It was difficult to please her.” Her son, who moved her into palatial comfort in Rancho Mirage, California, after Marty died (she had a five-bedroom house, with a cook, a gardener, three maids, and security guards), could do no wrong and do no right. Dolly saw his success but never saw the person. “She thinks she’s the big hit,” Sinatra said in a 1975 television interview. “If she were here with us now and she wanted to say something about me, she’d refer to me as ‘Frank Sinatra.’ While I’m sitting here.”
Beyond talent, beyond technique, the palpable but invisible power of every great star stems from the need to be seen and to be held in the imagination of the audience. This is especially true of Sinatra. The stillness, attention, and unequivocal adoration that were never there in Dolly were undeniable in the rapt enthusiasm of his listeners. “Thank you for letting me sing for you” was often Sinatra’s exit line at the end of his concerts. In song, he was his best self, and he craved to see that goodness reflected in the adoring eyes of others. “His survival was his mother audience,” MacLaine, who often toured with Sinatra, writes. “He desperately needed her to love him, appreciate him, acknowledge him, and never betray his trust. So he would cajole, manipulate, caress, admonish, scold and love her unconditionally until there was no difference between him and her. He and she had become one.” Offstage, Sinatra was dubbed the Innkeeper by his friends, because of the largesse of his hospitality; onstage, he operated more or less the same way. He fed others to insure that he got what he needed.
“Frank is a singer who comes along once in a lifetime, but why did he have to come in my lifetime?” Bing Crosby once joked. Sinatra’s voice was smaller and lighter than Crosby’s, but, as Whitney Balliett observed in these pages, “his phrasing and immaculate sense of timing gave it a poise and stature Crosby’s lacked.” Sinatra’s phenomenal impact, however, had to do not just with musical timing but with the timing of the technology that saturated the nation with his sound. As Henry Pleasants notes in “The Great American Popular Singers,” in 1930, only a decade before Sinatra made his name, the reigning crooner, Rudy Vallee, threw away the megaphone that had broadcast his sound and, by linking a borrowed NBC carbon microphone to amplifiers and several radios onstage, created a crude kind of concert amplification. (“I sing with dick in my voice” is how the notoriously foulmouthed Vallee explained his appeal.) Because of the lack of sophisticated miking technology, singers had had to sing in high ranges to play the room and to be heard above jazz bands. The microphone changed all this, bringing intimacy and articulation to the forefront of popular singing and making possible a whole new expressive style, which relegated the belters of the previous era—Al Jolson, Sophie Tucker—to history.
Sinatra himself began by singing with a megaphone, but the microphone soon became his totem. “To Sinatra, a microphone is as real as a girl waiting to be kissed,” E. B. White once wrote. Sinatra said, “Many singers never learned to use one. They never understood, and still don’t, that a microphone is their instrument.” Gripping the stationary mike with both hands and only occasionally moving it back and forth, he used it as a prop in a kind of foreplay. “You don’t crowd it, you must never jar an audience with it…. You must know when to move away from the mike and when to move back into it,” he wrote in Life. He added, “It’s like a geisha girl uses her fan.”
He also caught the wave of other sound innovations that were making song a pervasive part of daily American life. By 1938, more than half of all broadcast programs were recordings of popular music. In 1933, there were twenty-five thousand jukeboxes in the land; by 1939, there were two hundred and twenty-five thousand, and by 1942 four hundred thousand. The car radio, which was introduced in 1923 and became a standard feature by 1934, completely transformed the automotive experience. Record sales, which had dipped to $5.5 million in the depths of the Depression, had rebounded by 1940 to $48.4 million, and by 1945, when Sinatra was a household name, reached their all-time high of $109 million. Muzak, which had been successfully tested in New York hotel lobbies and dining rooms in 1934, had become a fact of industrial life by 1940 as America geared up for war. By the time Sinatra emerged from his brief apprenticeship as a ballad singer with touring dance bands and attained the status of solo act, the technology of enchantment was in place.
At first, Sinatra was more certain of his ability to enchant than was the trumpeter Harry James, whose struggling band he toured with for six months. “Well, what a voice!” the singer Connie Haines remembers James telling the young Sinatra, when James called him over to their table at the Rustic Cabin to offer Sinatra his first big break. “Then James said, ‘We gotta change that name.’ Frank pushed his tie up and made a direct turn. He says, ‘You want the voice, you take the name.’” According to Earl Wilson’s 1976 biography of Sinatra, when Down Beat asked James the name of his new singer, he replied, “Not so loud! The kid’s name is Sinatra. He considers himself the greatest vocalist in the business. Nobody ever heard of him, he’s never had a hit record, he looks like a wet mop. But he says he’s the greatest.” James went on, “If he hears you compliment him, he’ll demand a raise tonight.” Indeed, in January of 1940, Sinatra jumped ship and joined Tommy Dorsey’s band for a hundred dollars a week.
“You could almost feel the excitement coming up out of the crowds when that kid stood up to sing,” said Dorsey, whom Sinatra made the godfather of his firstborn child. “Remember, he was no matinée idol. He was just a skinny kid with big ears. I used to stand there so amazed I’d almost forget to take my own solos.” In fact, the secret of Sinatra’s vocal impact lay primarily in his observations of Dorsey’s trombone playing. “He would take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars. How in the hell did he do that?” Sinatra told his daughter Nancy in her book “Frank Sinatra: An American Legend.” “I used to sit behind him on the bandstand and watch, trying to see him sneak a breath. But I never saw the bellows move in his back. His jacket didn’t even move. So I edged my chair around to the side a little and peeked around to watch him. Finally, after a while, I discovered that he had a ‘sneak pinhole’ in the corner of his mouth—not an actual hole but a tiny place he left open where he was breathing. In the middle of a phrase, while the tone was still being carried through the trombone, he’d go ‘shhh’ and take a quick breath and play another four bars.”
Sinatra began to “play” his voice like Dorsey’s trombone. “I began swimming in public pools, taking laps under water and thinking song lyrics to myself as I swam holding my breath,” Sinatra said. “Over six months or so, I began to develop and delineate a method of long phraseology. Instead of singing only two bars or four bars at a time—like most of the other guys around—I was able to sing six bars, and in some songs eight bars, without taking a visible or audible breath. That gave the melody a flowing, unbroken quality and that’s what made me sound different.” His sound astonished even the professionals. “After the first eight bars, I knew I was hearing something I’d never heard before,” I was told by Jo Stafford, who had never seen or heard Sinatra before he walked onstage with her and the Pied Pipers for his début with Dorsey.
By 1941, the year before Sinatra went solo, Billboard had voted him the best male vocalist of the year. But the Sinatra phenomenon—what the press called Sinatrauma—began officially on December 30, 1942, at New York’s Paramount Theatre, only three months after Sinatra made an acrimonious departure from Dorsey’s band. “I hope you fall on your ass” was Dorsey’s parting shot to Sinatra, who, with the help of his new agency, had engineered a cash buyout from his original contract, which had called for a total of forty-three per cent of Sinatra’s lifetime earnings. He was now billed as the Extra Added Attraction to Benny Goodman and his Orchestra, and when he stepped onstage he walked into pandemonium. It was a watershed moment for him, and one that he had planned carefully, making sure that his press agent, George Evans, had primed the pump. “The dozen girls we hired to scream and swoon did exactly as we told them,” Evans’s partner, Jack Keller, said later. “But hundreds more we didn’t hire screamed even louder.”
Sinatra had fretted a long time about going solo. “The reason I wanted to leave Tommy’s band was that Crosby was Number One, way up on top of the pile,” he said during his Yale lecture. “In the open field, you might say, were some awfully good singers with the orchestras. Bob Eberly (with Jimmy Dorsey) was a fabulous vocalist. Mr. Como (with Ted Weems) is such a wonderful singer. I thought, If I don’t make a move out of this and try to do it on my own soon, one of those guys will do it, and I’ll have to fight all three of them to get a position.” Sinatra was the first to break through, and his fabulous success proved to be the thin end of the wedge for the Big Band Era and the beginning of the Vocalist’s Era. Within a month, his salary went crazy—from seven hundred and fifty dollars a week to twenty-five thousand—but not as crazy as his entranced fans. “Not since the days of Rudolph Valentino has American womanhood made such unabashed love to an entertainer,” Time wrote. “Girls hid in his dressing rooms, in his hotel rooms, in the trunk of his car,” Arnold Shaw wrote in his 1968 biography. “When it snowed, girls fought over his footprints, which some took home and stored in refrigerators.” When Sinatra returned to the Paramount Theatre again, in October, 1944, the line began forming before dawn and soon swelled to approximately twenty thousand fans, packed six abreast. Many members of the audience for the first show wouldn’t leave the theatre, and the frustrated crowd outside went berserk, in what became known as the Columbus Day Riot. Two hundred police, four hundred and twenty-one police reserves, twenty radio cars, and two emergency trucks were called in to control the rampaging, mostly teen-age girls.
Plato called songs “spells for souls for the creation of concord”; Sinatra’s crooning was balm to a republic desolated by the economic losses of the Depression and heading for war. “The best way to describe crooning is ‘Don’t make waves,’” says the lyricist and musical director Saul Chaplin, who, along with his collaborator Sammy Cahn, wrote for Sinatra at the beginning of his career. “Sinatra’s voice sings a straight line in a straight tone. There are no sudden louds or softs. The oscillation of the sound waves isn’t wide.” Sinatra—or Swoonatra, as he was dubbed—had another explanation for his appeal. “I was the boy in every corner drugstore, the boy who’d gone off to war,” he said. Actually, a punctured eardrum made him ineligible for service but available for leading roles. It was another piece of extraordinary good timing. The old stars were in the service, and the new ones wouldn’t emerge until the end of the decade:Sinatra had an open field on which to sing and dance. In 1945, he won a Special Award from the Academy for “The House I Live In,” a progressive ten-minute short about racial tolerance, and Modern Screen voted him the year’s most popular movie actor.
Of course, Sinatra’s best acting was not on film but in song. “When I sing, I believe, I’m honest,” he told Playboy in 1963. “An audience is like a broad. If you’re indifferent, Endsville.” Sinatra instinctively approached song as drama. “You begin to learn to use the lyrics of a song as a script, as a scene. I didn’t know I was doing that at the time, but I was,” he said years later on TV. “I try to transpose my thoughts about the song into a person who might be singing that to somebody else. He’s making his case, in other words, for himself.” Sinatra’s scrawny frame (he had a twenty-nine-inch waist, weighed a hundred and thirty pounds, and stood about five feet ten), his high voice, and his shy smile made him a safe object for teen-agers to adore. He personified the longing he sang about. “I’ll never thrill again to somebody new,” he confided in “I’ll Never Smile Again”; in “This Love of Mine,” whose lyrics he co-wrote, his sexual torment overwhelmed him: “It’s lonesome through the day/And oh! the night.”
Sinatra didn’t just sing a song; he made it his own. He brought a special urgency to his proprietorship. The songwriters he embraced, especially after he went solo—Cole Porter, Ira Gershwin, Johnny Mercer, Alec Wilder, E.Y. Harburg, Arthur Schwartz, Sammy Cahn, Jerome Kern, Lorenz Hart, Oscar Hammerstein—were the voices of the educated middle-class mainstream, whose sophisticated wordplay, diction, and syntax had an equipoise that contrasted with the social self-consciousness that so bedevilled Sinatra. According to Hamill, Sinatra built up his vocabulary doing crosswords, and in the seventies was reading Strunk and White’s “Elements of Style” for help with grammar. His signed articles were ghostwritten; he submitted to very few television interviews, and then only with friends like Arlene Francis or Aileen Mehle, in whose syndicated “Suzy” column he announced his first retirement, in 1971—people who he felt would protect him. But once he was inside the lyric, he had command of the language that he found paralyzing elsewhere. When he opened his mouth in song, he was calm; he was smooth; he was sensitive; he had no hint of the Hoboken streets in his pronunciation; what he called his “Sicilian temper” was filtered through the charm of lyrics and music into poetic passion. With other singers—Vic Damone, for instance, and Tony Bennett—you admired the technique; with Sinatra you admired the rendition. He presented the song like a landscape he’d restored, painting himself into the picture so masterfully that it was impossible to imagine it without him.
Sinatra’s appropriations of the standards was also the acquisition of the manners of another class. “It’s like stealing a Cadillac—except he’s stealing George Gershwin,” Hamill says. “‘You see what they got?’” Hamill says Sinatra said to him in the seventies as they watched Hamill’s children walk around the gardens of Monte Carlo. “‘They can go to the best schools. They can walk in everywhere, and they will know when they walk in what to do.’ I said, ‘What do you mean?’ He said, ‘Anything. Simple stuff. What fork to pick up.’” Hamill adds, “It’s no accident that Sinatra aspired in the music to grace. The ballads, in particular, have a grace to them that is really extraordinary. And that’s about knowing what fork to pick up.”
A decade after Sinatra’s Paramount triumph, a headline in the World Telegram & Sun put what he came to call his Dark Ages into bold relief: “gone on frankie in ’42; gone in ’52.” A new youngster, Johnnie Ray, had the nation’s ear, and Sinatra’s records no longer sold in their familiar quantities. “What do you think is happening?” he asked the columnist Earl Wilson. He added, “I’m not throwing in any sponge to Johnnie Ray!” Sinatra’s career, his marriage, and his voice were showing visible signs of cracking under the pressure of his momentum, and the fans who had adored his crooning were not so adoring of his bad behavior, which they now read about regularly in the papers. In 1947, Sinatra had managed to get himself photographed with Lucky Luciano and other mobsters in Havana, thereby giving the syndicated columnist Robert Ruark a three-part field day. “shame, sinatra!” was the first column’s banner. Then, there was the issue of Sinatra’s egalitarian political opinions, which let him in for Red-baiting by the right-wing press; he was labelled a Communist in the F.B.I. files. But of all Sinatra’s sins the most unacceptable to the public were his unabashed extramarital exploits. According to press reports, he appeared to be making an almost heroic effort to bed the female population of an entire industry—as though he were hellbent on proving himself through conquest as his career dipped. In the late forties and early fifties, he was frequently photographed with the objects of his desire, among them Marilyn Maxwell, Lana Turner, and, especially, Ava Gardner; it was a list whose ranks would ultimately include Joan Crawford, Marlene Dietrich, Kim Novak, Lauren Bacall, Angie Dickinson, Gloria Vanderbilt, Natalie Wood, Marilyn Monroe, Sophia Loren, Judy Garland, and Juliet Prowse. “Sinatra’s idea of paradise is a place where there are plenty of women and no newspapermen,” remarked Humphrey Bogart, who was Sinatra’s good friend and the model for his emerging “tough guy” persona. “He doesn’t know it, but he’d be better off if it were the other way around.”
Indeed, Sinatra, who had learned the importance of publicity from Dorsey, and had launched himself on the press with Presidential lavishness in the forties (he bought the columnists dinners, jewelry, engraved Dunhill lighters), now lashed out at the journalists who were chronicling his decline. “To tell Louella Parsons to go fuck herself was quite a major thing in those days, when everybody was quivering,” Sinatra’s buddy Tony Curtis says. And Parsons wasn’t the only writer to get a Sinatra jolt via Western Union. He also took on Westbrook Pegler, who had called him a “fellow traveller,” and he struck the Daily Mirror’s reactionary columnist Lee Mortimer on the side of the head—a blow that landed Mortimer on the floor and Sinatra with an out-of-court settlement that cost him twenty-five thousand dollars. “He gave me a look,” Sinatra said before lawyers sanitized his explanations. “It was one of those ‘Who do you amount to?’ looks. I followed him out. I hit him. I’m all mixed up.”
The force of Sinatra’s explosive unpredictability could be devastating. His close friend Leonora Hornblow says, “It’s instant. It’s uncontrollable. It’s like a volcano. You want to run away. He’s got lungs, mind you. When he yells, you hear it.” Anyone who knew Sinatra well also knew what Sammy Cahn called “the blue-eyed ray”—the intense beam of romance or rage that Sinatra emitted. “That look he also locked into very young, like he did his conception of women,” Shirley MacLaine says. “He sort of gave me that look which was a look between ‘I’ll protect you’ and ‘Do you want to have an affair?’ You couldn’t tell when one stopped and the other started.” Lauren Bacall, too, felt the powerful manipulation of Sinatra’s stare. “He would be looking at you as if you were It. Then he’d be laughin’ and jokin’ and he walked off by himself. No one was gonna tie him down,” she says. “I think one of the reasons that he and I split—it was his doing, not mine—was that he felt he never could live up to the kind of a man and husband Bogie was. He knew it would never work, because he’d be cheating on me in five minutes—because that’s what he did. That’s about the Swingin’ Guy. That’s about ‘It’s quarter to three, there’s no one in the place except you and me.’ ”
Sinatra’s womanizing ultimately threatened to undermine what success he still had. In the late forties, George Evans told Earl Wilson at the Copacabana, “Frank is through. A year from now you won’t hear anything about him.” He added, “You know how much I’ve talked to him about the girls. The public knows about the trouble with Nancy, and the other dames, and it doesn’t like him anymore.”
The siren that lured Sinatra onto the rocks was Ava Gardner, who was, like him, a card-carrying romantic narcissist—someone as self-absorbed, impetuous, and powerful as he was. In her 1990 autobiography Gardner recalls Sinatra’s coming over to her and her first husband, Mickey Rooney, at a Los Angeles night club with his celebrity smile at full candlepower: “He did the big grin and said ‘Hey, why didn’t I meet you before Mickey? Then I could have married you myself.’” She adds, “Frank Sinatra could be the sweetest, most charming man in the world when he was in the mood.” And for a while he was. When they first got together, Gardner took him back to her little yellow house in Nichols Canyon. “Oh, God, it was magic,” she writes. “And God Almighty, things did happen.”
Gardner was Sinatra’s match in brazenness and in sexual independence, and their relationship was tempestuous. “The problems were never in the bedroom,” Gardner once said. “We were always great in bed. The trouble usually started on the way to the bidet.” In New York, after one jealous argument, Sinatra called Gardner’s adjacent suite. “I can’t stand it anymore,” he said. There was a gunshot. Gardner bolted into his room. Sinatra was lying face down, the smoking revolver still in his hand. “Frank! Frank!” Gardner screamed. Sinatra looked up. “Oh, hello,” he said. He had shot the mattress.
Their affair, which the public followed as avidly as they did “Stella Dallas,” finally destroyed Sinatra’s marriage. On Valentine’s Day of 1950, Nancy Sinatra petitioned for a legal separation. The press response was vitriolic, and shortly thereafter, on April 26th, at the Copacabana, Sinatra opened his mouth to sing and nothing came out. “It became so quiet, so intensely quiet in the club—they were like watching a man walk off a cliff,” Sinatra’s accompanist and conductor on that night, Skitch Henderson, recalled. “His face chalk white, Frank gasped something that sounded like ‘good night’ into the mike and raced off the floor, leaving the audience stunned.” His throat had hemorrhaged, through stress and overwork. (“I didn’t speak for forty days,” he told Arlene Francis about his recovery. “For forty days I didn’t say a single word.”)
Sinatra married Gardner in 1951; they separated eleven months later. “I remember exactly when I made the decision to seek a divorce,” Gardner writes. “It was the day the phone rang and Frank was on the other end, announcing that he was in bed with another woman. And he made it plain that if he was going to be constantly accused of infidelity when he was innocent, there had to come a time when he’d decided he might as well be guilty.” In the short time that they were husband and wife, though, Gardner, whose star was in the ascendant, did what she could to bolster Sinatra’s falling star. Her ten-year contract with M-G-M contained a clause stipulating that “at some time prior to the expiration of her contract, we will do a picture with her in which Frank Sinatra will also appear.” Although they never worked together, Gardner interceded on Sinatra’s behalf with Columbia’s president, Harry Cohn, to help her husband land the part of Maggio in “From Here to Eternity.” And Gardner, in her alcoholic, reclusive later years, was supported by Sinatra. Through their jealous rages, their sexual betrayals, and their reconciliations, Sinatra and Gardner were sensational public fodder; their private hell was memorialized by him in the outstanding “I’m a Fool to Want You,” which he co-wrote and recorded in 1951, apparently so overcome with feeling that he did it in one take and left the session:
I’m a fool to want you
I’m a fool to want you,
To want a love that can’t be true,
A love that’s there for others too….
Inthe meantime, the public seemed indifferent to the old standards and avid for novelty. At Columbia Records, Mitch Miller, the powerful producer who found the mother lode of “Mule Train” and Frankie Laine, was trying to find a commercial avenue for Sinatra. Although Miller got Sinatra to do some up-tempo numbers, including the seminal “Birth of the Blues,” in which Sinatra defines the swinging, hard-edged style of his middle years, he also persuaded Sinatra to record “Tennessee Newsboy,” with washboard accompaniment, and “Mama Will Bark,” with the zaftig Dagmar, and Donald Bain barking like a dog. (“The only good business it did was with dogs,” Sinatra quipped, although the song got to No. 21 on the charts.) These recordings represent the nadir of Sinatra’s musical career, but they were also a barometer of Columbia’s mismanagement and Sinatra’s rudderless desperation. Miller was the donkey on whom Sinatra pinned the tail of his decline. “You cannot force anyone to do a song. People don’t understand this,” Miller told Will Friedwald in “Sinatra!: The Song Is You.” “Sinatra said I brought him all these shit songs, I forced him to do shit songs.” Certainly Sinatra disliked Miller’s control-room intrusions into his music-making. As Sinatra’s regular drummer in those days, John Blowers, recounted to Friedwald, “All of a sudden one day finally, quietly, he looked at the control room and said ‘Mitch, out’—and Frank always pointed his finger—and he said ‘Don’t you ever come in. Don’t you ever come into the studio when I’m recording again.’ Mitch never came again. Frank wouldn’t permit it.” In Sinatra’s final months at Columbia, his song selections seemed to be a message to his producer: “There’s Something Missing,” “Don’t Ever Be Afraid to Go,” and “Why Try to Change Me Now?” Years later, Miller caught up with Sinatra in Las Vegas, and went to shake his hand, seeking a kind of reconciliation. “Fuck you,” Sinatra said. “Keep walking.”
The losses piled up. In 1949, M-G-M let Sinatra go. In 1950, George Evans died, at the age of forty-eight. In 1952, “Meet Danny Wilson” flopped, and Universal refused to renew Sinatra’s option for a second film; he was dropped by Columbia Records; CBS cancelled “The Frank Sinatra Show”; and he was released by his theatrical agency. “I was in trouble. I was busted, and I must say that I lost a great deal of faith in human nature because a lot of friends I had in those days disappeared,” Sinatra recalled at his Yale lecture. “I did lie down for a while and had some large bar bills for about a year.” Then, he explained, “I said, ‘O.K., holiday’s over, Charlie. Let’s go back to work.’”
But who would hire him? When his new agent, Sam Weisbrod, called Alan Livingston, the A. & R. man at Capitol Records, and asked if he would sign up Sinatra, Livingston said yes. “You would?” Weisbrod replied. Livingston explains, “I’m quoting him verbatim. I said, ‘Yes.’ He said, ‘You would?’ I mean, for an agent to react that way!” In 1953, Livingston, who later signed the Band and the Beatles, signed Sinatra to a one-year contract with six one-year options and a five-per-cent royalty. “Frank Sinatra was totally down and out. I mean he was gone. In addition, his voice was kind of gone,” Livingston says. “At the time I signed Frank, we had our national sales meeting. There were around a hundred and fifty salesmen, branch managers, regional managers there. I would play them upcoming records. I’d tell them about new artists. I said, ‘I want to tell you this: we’ve just signed Frank Sinatra.’ The whole place went ‘Ooh’—like ‘Oh, God, what are you doing to us?’ They were just so unhappy about it.” Livingston adds, “I remember my response. I said, ‘Look, he’s the greatest singer I’ve ever heard. He’s in trouble, and he hasn’t done anything for a long time. All I know how to deal with in my job is talent. This is talent.’”
At Capitol, Sinatra began to pull out of his skid. His songs seemed to announce it. On April 30, 1953, teamed with a brilliant new thirty-two-year-old arranger, Nelson Riddle, whom Livingston had suggested, Sinatra cut “I’ve Got the World on a String” and “Don’t Worry ’Bout Me.” “Sinatra was elated by the sound,” Ed O’Brien and Robert Wilson write in “Sinatra 101: The 101 Best Recordings and the Stories Behind Them.” “During the playbacks that evening, Sinatra made the rounds in the studio, gleefully slapping the backs of musicians and technicians, and telling many of them that he was back.”
Then, in August, “From Here to Eternity” was released, and Sinatra was reborn for sure. “By getting stomped to death in that movie, he did a public penance,” Mitch Miller told Friedwald. “You can chart it. From the day the movie came out, his records began to sell.” Sinatra was thirty-eight when he received the Academy Award for Best Supporting Actor in the film. He gave up his psychiatrist and took up permanent residence in his success; by 1954, the Sinatra-Riddle partnership had produced the first hit single he’d made in seven years, “Young At Heart,” which went to No. 2 on the charts.
Sinatra now had a public history of troubles and new triumphs to take on the road, and his songs were increasingly viewed by his audience and by him as a kind of autobiography: “All or Nothing at All”—the gamble on his talent; “I’m a Fool to Want You”—unrequited love of Ava; and now “I’ve Got the World on a String”—his comeback. But the new Sinatra was not the gentle boy balladeer of the forties. Fragility had gone from his voice, to be replaced by a virile adult’s sense of happiness and hurt. “It was Ava who did that, who taught him how to sing a torch song,” Nelson Riddle said. “That’s how he learned. She was the greatest love of his life and he lost her.” As Sinatra put it, “You have to scrape bottom to appreciate life and start living again.” In the forties, his vocal experiments had to do primarily with smoothness; in the fifties, he discovered syncopation, and the new swagger of his voice broadcast the cocky sense of possibility which was America’s mood as well as his own. In “Taking a Chance on Love,” which he recorded on April 19, 1954, he sang, “Now Iprove again/That I can make life move again/Mmm—I’m in a groove again/Takin’ a chance on love.”
The phenomenon of Sinatra as a crooner and playboy had somewhat obscured the public perception of him as a musician. But Riddle’s arrangements, which were not overly busy, showed off Sinatra’s musicianship to sensational advantage, and left room for him to act his new part as Swinger. “The man himself somehow draws everything out of you,” Riddle told Jonathan Schwartz on WNEWin the early eighties. “And I always felt that my rather placid disposition had a beneficial effect on him.” Together, they created the classic Sinatra sound—as luck would have it, just when technology produced both high fidelity and the long-playing record. “Never before had there been an opportunity for a popular singer to express emotions at an extended length,” Schwartz says. As many as sixteen songs could be held by the twelve-inch L.P., and this allowed Sinatra to use song in a novelistic way, turning each track into a kind of chapter, which built and counterpointed moods to illuminate a larger theme. In their seminal L.P.s—“In the Wee Small Hours,” “Frank Sinatra Sings for Only the Lonely,” “Songs for Swingin’ Lovers!,” and “A Swingin’ Affair!”—Sinatra and Riddle came up with the first concept albums. Between April, 1958, and April, 1966, Sinatra had no Billboard Top Ten singles, but he had twenty Top Ten albums. “Only the Lonely,” which came out in 1958, stayed on the charts for a hundred and twenty weeks; the 1959 follow-up album, “Come Dance with Me,” remained for a hundred and forty weeks.
From his earliest Dorsey days, Sinatra had understood the importance of arrangers. “When the arranger would run down the orchestration, he would hear where the figures were, and when he sang the song he would arrange to clear it so those figures came through,” Saul Chaplin, who watched Sinatra adapt to Dorsey’s orchestrations, says. “He’d drop a note which he could have held because he knew the over-all is what counts, not just his voice alone.” In performance, Sinatra often honored this division of labor by announcing the arranger and the songwriter of a number before he sang it. With Riddle, he was patient and precise about what he wanted. “When you hear a Frank Sinatra album, it’s the product of Frank Sinatra’s head,” Riddle told Schwartz. “He was always very coherent about what he wanted—where the crescendi should take place, where the diminuendos, the tempi, naturally the key. Sometimes it became almost painful in discussing an album of twelve or fourteen songs. It was a very precise, tense atmosphere. I would practically blow my stack because we’d take almost an hour on each piece. Then human nature would set in after five or six or seven or eight of those. He’d get tired. He’d say, ‘Do what you want with the rest.’ That would be the end of the thing, and we were both, I think, somewhat relieved.”
The result Riddle achieved in “I’ve Got You Under My Skin” was, he said, “a sort of a cornerstone recording for both him and me.” The arrangement starts with a comfortable, loping rhythm that Riddle called “the heartbeat rhythm” (“Sinatra’s tempo is the tempo of the heartbeat,” he said) and then sets up a marvellous instrumental tension around Sinatra’s voice. Riddle always found little licks—certain spicy, nearly out-of-key notes—that would tease the key, and added the glue of “sustaining strings” almost subliminally to the rhythm and woodwind sections. At the instrumental breaks in the songs, Riddle gave solo voices to oboes, muted trumpets, piccolos, bassoons; in “I’ve Got You Under My Skin,” it was to Milt Bernhart’s trombone, which whipped up the excitement until Sinatra joined the song again and brought it back to the heartbeat rhythm where it had begun. Sinatra had wanted an extended crescendo; Riddle provided one that was longer than had ever been heard in an organized arrangement.
The song won a fans’ poll as the all-time-favorite Sinatra recording; it “changed American popular music, and that is not overstating the case,” Schwartz says. “Nothing was the same after that specific arrangement and also the sound of the ‘Songs for Swingin’ Lovers!’ album itself.” Sinatra had found his groove. His singing in this period was more than a sound; it was an attitude. He gave us words, postures, rhythms—a sense that sex and life were going to be a a big “wowie,” as he sang in “Me and My Shadow.” The postwar party had begun, and while the fifties were stalled in normalcy, Sinatra had about him a whiff of the libertine. His style—the thin, sensitive line of his look and of his singing—had the immanence of the hip combined with the articulateness of the traditional, to which all of us preppy white boys could relate. We dressed Sinatra, doing up our paisley Brooks Brothers ties into Windsor knots. We talked Sinatra: “Charlies” for breasts, “gas” for fun, “bird” for pecker, the suffix “-ville” added to as many words as we could work into our new patter. We wanted to go to the party, and it seemed that Sinatra had always been there.
After the humiliations of his decline, nothing so moved Sinatra as the spectacle of himself as a powerhouse: big talent, big guys around him, big bucks behind him, big connections to the mainstream and to underworld power. “He used his success in film, in singing, and in business to pump up the persona of untouchable,” Tony Curtis says. “Notice I don’t bring up the Mafia. He in himself was his own godfather. He ran his own family and his friends like that. Untouchable.”
Before his comeback, Sinatra had survived hand to mouth, primarily on borrowed money; after it, he laid the groundwork for an empire. Sinatra, who lives in Beverly Hills but who once kept homes in New York and London as well, ruled over his kingdom in his heyday primarily from his compound in Rancho Mirage, which grew over the years into a kind of metaphor of his aggrandizement, with a helipad, a swimming pool, tennis courts, a screening room, and a state-of-the-art kitchen with full twenty-four-hour service. The compound also boasted two two-bedroom guesthouses, each with his-and-hers bathrooms and, in “the Kennedy room,” a red White House hotline telephone that was originally installed for an aborted visit by J.F.K., in 1962. (Much to Sinatra’s rage, the President, on orders from Bobby Kennedy to distance himself from Sinatra and his Mafia connections, stayed instead with Bing Crosby, in nearby Palm Desert.)
Sinatra’s lavish entertaining bespoke not just a man of talent but a man of property. He owned nine per cent of the Sands Hotel in Las Vegas, which he turned almost single-handedly into an entertainment mecca; he became vice-president of the corporation, and earned a hundred thousand dollars for each week he performed, until falling out with the hotel, in 1967. For a time in the sixties, he also owned fifty per cent of the Cal-Neva Lodge in Lake Tahoe. In those days, buttons began to appear with Sinatra’s face on them, bearing the motto “it’s sinatra’s world, we just live in it.” And so it seemed. Sinatra also acquired large interests in a small charter airline, a music-publishing house, radio stations, restaurants, and real estate. He formed Essex Productions and received as part of his fee twenty-five per cent of “Pal Joey”; another Sinatra company received the same percentage for “The Joker Is Wild,” in which he starred.
By the end of the decade, Sinatra had earned so much money for Capitol that he wanted his own label. He proposed a fifty-fifty split with Capitol, who would distribute—a deal that was unheard-of in those days but is common now. When Capitol refused, Sinatra formed his own record company, Reprise Records; he pronounced it with a long “i,” as in “reprisal.” “Fuck you! Fuck your company!” Sinatra shouted over the phone to Alan Livingston when Livingston tried to reach a last-minute agreement with him. Livingston recalls, “Frank said, ‘I’m going to destroy that round building. I’ll tear it down.’” Although Sinatra was forced to make four more albums for Capitol, Capitol continued after he was gone to make Sinatra albums from unreleased recordings and sell them at cut prices. “The market was flooded with our Sinatra albums,” Livingston says. “Reprise got killed. Nobody was taking their product. Then Jack Warner came in and bailed Sinatra out.” (Sinatra sold two-thirds of Reprise to Warner Bros. in 1963, for more than three million dollars’ capital gain.)
Onstage, Sinatra was in control of his world and beyond hurt. Offstage, he was fearful and somewhat paranoid. His paternal advice to Nancy was “Be aware. Be aware of everything around you.” What wealth brought him was a liberating sense of control over life. “I remember we were on a plane flying from Las Vegas to Palm Springs,” Aileen Mehle says of a trip she took with Sinatra in the early sixties. “He had paper bags full of, I think, hundred-dollar bills. Loaded. Hundreds of thousands. He upended the bags in the middle of the plane and started throwing the money up in the air. Talk about playful! He said, ‘I’m celebrating, because for the first time I have a million dollars cash in the bank that I don’t give a damn what I’m going to do with.’”
Among his friends, Sinatra has always been known for impulsive, awesome acts of generosity—those grand gestures that Sicilians call la bella figura. “I always felt I could call and say, ‘Frank, I’m in trouble. I need a hundred thousand dollars,’” Jo Stafford says. Sinatra once sent his friend the actor George Raft, who was under indictment for federal-income-tax evasion, a signed blank check with a note saying “To use if you need it.” When Phil Silvers’ partner Rags Ragland died just before they were to open the Copacabana, in 1946, Sinatra flew across the country to surprise the comedian and play straight man. “When someone was down on his luck, Frank was like the Marines. He was there,” I was told by the late actress-turned-psychotherapist Ruth Conte, the former wife of the actor Richard (Nick) Conte, who was part of Sinatra’s circle in the fifties. “When Nick left me, Frank called me. ‘How ya doin’, baby.’ A kindness that was also an assertion of power. It was so reassuring to him to be able to use it.”
Indeed, Sinatra’s compulsion to assuage his friends’ anxieties was a way of keeping his own at bay. “You sometimes feel like you want to run away from him,” Burt Lancaster said. “Because if you say to Frank, ‘I’m having a problem,’ it becomes his problem. And sometimes maybe you’d like to try and work it out yourself.” Sinatra’s need to protect made him an extraordinary but contradictory friend. “If you helped him more than he helped you, the friendship was doomed because the balance he wanted had been tipped,” MacLaine writes. “He was a happy man when he was able to come to my rescue. ‘Oh, I just wish someone would try to hurt you so I could kill them for you,’ he’d say.”
Inevitably, Sinatra had trouble acknowledging the generosity of his friends and colleagues. “He just isn’t built to give out compliments,” Riddle has said of him. After Sinatra got an Academy Award, he said, “I did it all myself”; once, in a shouting match with a press agent who had the temerity to suggest that Sinatra was dependent on the public, Sinatra shot back, “I am not! I have talent and I am dependent only on myself!” This separation of himself from others, which accounts for his arrogance, also accounts for the special quality of loneliness in his singing. “He understood loneliness better than any other person of his generation,” Hamill says. “I mean a certain kind of urban loneliness.” But what Sinatra evokes is not strictly urban. It is a very particular American loneliness—that of the self adrift in its pursuit of the destiny of “me,” and thrown back onto the solitude of its own restless heart.
As a singer, of course, Sinatra could be all-giving and all-conquering all the time. The cocked hat, the open collar, the backward glance with the raincoat slung over the shoulder, the body leaning back with arms wide open in song—these images of perfect individualism dominated the albums of the fifties. Sinatra was flying high. “Come fly with me!/Let’s fly!/Let’s fly away!” he commanded the world. But these lyrics also hint at Sinatra’s escape into success—into an empyrean where no one could touch or judge him: “Up there! Where the air is rarefied/We’ll just glide, starry-eyed.” Sinatra retreated into his own de-luxe isolation; instead of intimacy he offered the audience bits of his legendary public story. Some of his songs invoked his family (“Tina,” “Nancy with the Laughin’ Face”); in “Me and My Shadow” he referred to his saloonkeeping philosophes Jilly Rizzo and Toots Shor. Sinatra stood before an audience as a person who had caroused with killers and kings. He’d been married to the most beautiful woman in the world. He had won and lost and now won again. All this made him more interesting as a performer than anything he sang. Sinatra’s best songs of the period—“All the Way,” “Call Me Irresponsible,” and especially “Come Fly with Me”—were written by Sammy Cahn, who had roomed with Sinatra, travelled with Sinatra, and lived a lot of Sinatra’s story with him. The material was Sinatra. “Sammy’s words fit my mouth the best,” he told the producer George Slaughter.
But lyrics, like everything else, could suffer from Sinatra’s egotism. “Ira Gershwin hated that Sinatra took ‘A Foggy Day’ and sang ‘I viewed the morning with much alarm,’” the singer Michael Feinstein, who was for a long time Gershwin’s assistant, says. “The lyric is ‘I viewed the morning with alarm.’ It drove Gershwin crazy, because he felt the word ‘much’ weakened what he originally wrote.” Leonora Hornblow tells of an evening at actor Clifton Webb’s when Cole Porter was present: “Frank fiddled with the lyrics. I think it was ‘I Get a Kick Out of You’—you know, ‘You give me a boot.’ Cole got up and walked out. Cole had perfect manners. For him to do that while somebody was singing was like stripping his clothes off.” Sinatra revered Porter (he leased Porter’s apartment at the WaldorfTowers), but he also thought Porter “a snob,” whereas Cahn wrote lyrics that had Sinatra’s common touch. Cahn spoke and wrote in the same demotic, tough-talking, breezy manner (“Hey there, cutes, put on your Basie boots”). “Sammy saw himself as Frank,” his widow, Tita Cahn, says. “Frank without the voice, without the looks.” And Cahn played a large part in building the image of the loosey-goosey, unpredictable ring-a-ding guy. He and the composer Jimmy Van Heusen were commissioned by Sinatra to write a song using Sinatra’s catchphrase for his first Reprise album, which was called, not surprisingly, “Ring-a-Ding-Ding!” The phrase—like Shakespeare’s “Hey nonny nonny”—thumbed its nose at meanings and sincerity. Sinatra’s songs of this period—the late fifties and early sixties—however beautifully rendered, don’t express the truth of his hurt or the exhilaration of his innocence. “Ring-a-Ding-Ding!,” for instance, is a slick piece of emotional coasting. It substitutes pop romance for Sinatra’s real-life, orgiastic refusal to suffer:
Life is dull, it’s nothing but one big lull,
Then presto! You “do a skull” and find that you’re reeling,
She sighs, and you’re feeling like a toy on a string,
And your heart goes ring-a-ding-ding! Ring-a-ding-ding!
Drink played a large part in Sinatra’s ring-a-ding arrogance. “Frank Sinatra is, in the most dramatic and classical sense, an alcoholic,” Jonathan Schwartz says. “There’s a grandiosity, a fury, a self-pity, a night viciousness.” He adds, “He made drinking an asset. He made it romantic.” In the fifties, foreshadowing the performing indulgences of the sixties, Sinatra began bringing a tumbler of Scotch and a pack of cigarettes onstage. “Nobody’s ever done that before or since, have they?” the author and renowned teacher of dramatic singing David Craig says. “Abusing himself like no singer in history.” It was another way for Sinatra to flaunt his invincibility. “He’s trying to demean his gift,” Tony Curtis says. “He just wants to show you—like a juggler or a guy who works the tightrope, he goes up there with a drink in his hand and a cigarette butt—that he can still do it.”
“If you can use some exotic booze/ There’s a bar in far Bombay,” Cahn wrote memorably in “Come Fly with Me”; he also provided the Rat Pack with the ensemble hymn “Mr. Booze” in the movie “Robin and the Seven Hoods.” Cahn had Sinatra’s number, and he found a discreet way of turning Sinatra’s quixotic lapses to public advantage. “Call me irresponsible,” he wrote. “Call me unreliable,/Throw in undependable too.” He understood that Sinatra’s bad behavior was romantic in song; in life, he saw it differently. Tita Cahn recalls, “Sammy used to say that Frank was a man who kept putting the dream to the test, pushing it too far, hoping that someone would hit him and he’d be awakened. But nobody did. The dream wouldn’t go away.”
“Frank created this romantic figure he wanted to be,” Lauren Bacall says. “There was something about him that was a little unreal. I think he fantasized a bit.” She continues, “He was away singing at some club, and he would call me and say, ‘I’m coming home tonight. I want you to be at the house when I get there.’ I—jerk—thought, How glamorous. I’d get in my car, drive up to his house. I’d be standing there by myself, then suddenly in he’d walk. Oh, God, what a great moment! Then just as easily that night he could throw me out. He was capable of that kind of change.” When news of Sinatra’s engagement to Bacall was leaked to the press by her agent and Sinatra’s friend Irving (Swifty) Lazar in 1958, Sinatra immediately dropped her. Years later, when he was seeing Mia Farrow, Bacall met him and chatted warmly with him at a party given by Lazar. “Frank never mentioned to me that he knew that Lazar had been responsible for the press, never said a word to me about it,” Bacall goes on. “Swifty was sitting at another table across the room. Before Sinatra left, he got up and walked over to Lazar’s table. He put his hands on the tablecloth and pulled the fucking tablecloth off the table—all the glasses, the plates, everything fell on the floor. He said, ‘And you’re the one who’s responsible for what happened between us!’ He turned around and walked out.”
Sinatra, whom Peter Lawford called “the lovable land mine,” was at once cursed and blessed by this notoriously thin skin. His hypersensitivity made him both hell on a short fuse and more sensitive to emotion in a lyric. Sinatra seemed compelled to discharge any unsettling feeling as quickly as possible. “It’s not something I do deliberately. I can’t help myself,” he told Playboy. “If the song is a lament about the loss of love, I get an ache in my gut. I feel the loss and I cry out the loneliness.” Song, like rage, had the ability to put Sinatra “beside himself”; and, like song, his fury served as a kind of antidepressant. “He never gave you the reality,” Curtis says of Sinatra’s singing persona. “I saw dissatisfaction, an anger, a frustration from that immigrant background of his.” Even backstage in Las Vegas, when Sinatra walked off after a successful gig, Curtis noticed that Sinatra’s face “was drawn and ready for a fight.” Curtis says, “When he got up onstage, he seemed to say, ‘Fuck you, motherfuckers. Sit quiet. I’ll show you something.’ That was part of the kick.”
“The façade of being macho and strong grew as his career grew,” says Nancy Sinatra, Sr. “He became part of that image. He was never quite that at all, believe me.” But Sinatra was pleased with his reputation for toughness. When Al Capp mythologized him as Danny Tempest in the cartoon strip “Li’l Abner,” Sinatra thanked him. “He believes in punishment. He’s a bully,” says Jonathan Schwartz, who for more than a decade has played nothing but the Chairman of the Board on his “Sinatra Saturday” program, and was forced to take a three-month “sabbatical” from WNEW after he called the final third of Sinatra’s 1980 “Trilogy” album “a mess of narcissism.” In “My Way,” the anthem of Sinatra’s later years, which Sinatra came to dislike, he sang, “The record shows I took the blows/And did it my way.” Actually, the record shows that other people took the blows. In 1967, after his credit was stopped at the Sands in Vegas, Sinatra exacted retribution by signing a contract with Caesar’s Palace and then going on a tear at the Sands: threatening dealers, driving a golf cart through a plate-glass window, breaking furniture and trying to set it alight, and finally confronting the executive vice-president, Carl Cohen. “I’ll bury you, you son-of-a-bitch motherfucker,” he told Cohen, whereupon Cohen removed the caps from Sinatra’s front teeth. (Sinatra later laughed it off. “Never punch a Jew in the desert,” he said.) “I think the rage might have been a double rage,” Pete Hamill says of Sinatra’s wild outbursts. “A rage against the object of his anger and a rage against himself in some way, for losing his temper and letting this classy façade crumble so easily.”
As Sinatra’s power grew over the years and he became a kind of law unto himself, he dealt with conflict by withdrawing the favor of his presence from people. After dropping Bacall, Sinatra encountered her by chance in Palm Springs. “He looked at me as if I were the wall. It was so terrifying. I have never had that experience before or since,” she says. Friends were banished sometimes for a week, sometimes forever. Phil Silvers was cut off in the fifties after CBS programmed “The Phil Silvers Show” opposite ABC’s “The Frank Sinatra Show.” “You had to go Fridays, huh?” Sinatra said, and stopped speaking to Silvers for sixteen years. Peter Lawford bit the dust twice—initially when he was Ava Gardner’s first date after her divorce from Sinatra. “He threatened to kill me and then didn’t speak to me for five years,” says Lawford, who was struck off again, after the Kennedys’ postelection snub of Sinatra’s Rancho Mirage estate, simply because he was married to J.F.K.’s sister Patricia. In 1959, when Sammy Davis, Jr., complained about Sinatra to a Chicago journalist, saying, “I don’t care if you are the most talented person in the world. It doesn’t give you the right to step on people and treat them rotten,” he spent a couple of months in purgatory, and was returned to the fold only after he offered a public apology for his outburst.
The atmosphere of intimidation that surrounded Sinatra was reflected in the jokes of the Vegas comedians. Shecky Greene: “Frank Sinatra once saved my life. I was jumped by a bunch of guys in the parking lot and they were hitting me and beating me with blackjacks when Frank walked over and said, ‘That’s enough, boys.’” Don Rickles: “C’mon, Frank, be yourself. Hit somebody.” Jackie Mason doesn’t know what he did to offend Sinatra, but while he was playing the Aladdin Hotel in the early eighties, Sinatra came onstage after Mason’s set and began berating him. “‘The jerk-off rabbi.’ ‘Who the fuck is he?’ This, that, ‘Fuck him,’” Mason says. “I don’t even know what happened. All I know is that a couple of weeks later, I opened the door of a car—ping!—a fist came in and busted me in the nose and before I could open my eyes he disappeared. I asked a lot of wise guys. They didn’t say it was Sinatra. In my heart of hearts, I think it must have come from Sinatra.” Even if Sinatra’s menace wasn’t verifiable, it was part of his aura—a rough justice underlined by his friendship with punks and Presidents.
The most powerful among Sinatra’s powerful friends was, of course, John F. Kennedy, for whom he acted as both fund-raiser and pander. The fun-loving Kennedy, whom Sinatra nicknamed Chicky Boy, enjoyed carousing with Sinatra’s star-studded cronies; Sinatra repaid the honor of the association by calling his clique the Jack Pack, for a brief time, and even introduced Kennedy to one of his girlfriends, Judith Campbell. Sinatra got to visit Hyannis Port, to travel in the President’s private plane, and to cruise with the President on the Honey Fitz; he escorted Jackie Kennedy, who didn’t want him in the White House, to the inaugural gala he’d organized.
If Kennedy’s high rank confirmed the brightness of Sinatra’s star, the darkness of Sinatra’s past was confirmed by the wise guys he was drawn to. Over the years, Sinatra rubbed shoulders with a gallery of hoodlums: Willie Moretti, Joe Fischetti, Lucky Luciano, Carlo Gambino, and, especially, Sam Giancana, who was the head of the Chicago mob in the fifties, and who called Sinatra the Canary. Part of Sinatra’s freewheeling impudence came from the wisdom of the underclass—the knowledge that crime was free enterprise turned upside down and that there was a slim difference between being a killer and making a killing. “If what you do is honest and you make it, you’re a hero,” Sinatra said. “If what you do is crooked and you make it, you’re a bum. Me—I grabbed a song.” Sinatra walked a thin line between respectability and rapacity. He had learned the manners of the ruling class, and he owned all their pleasures; what the mobsters offered him was the flip side—their lack of propriety. They lived the darkness that Sinatra’s bright public persona could only hint at in song. “He was in awe of them,” Bacall says. “He thought they were fabulous.”
Onstage, where the association gave Sinatra an aroma of toughness and menace, he sometimes joked about the wise guys; offstage, he was loath to talk. When Hamill first raised the touchy issue of the mobsters with Sinatra, Sinatra said only, “If I talk about some of those other guys, someone might come knockin’ at my fuckin’ door.” But he later went on, “I spent a lot of time working in saloons…. I was a kid…. They paid you, and the checks didn’t bounce. I didn’t meet any Nobel Prize winners in saloons. But if Francis of Assisi was a singer and worked in saloons, he would’ve met the same guys.”
A nineteen-page Justice Department memorandum prepared in 1962 suggests that Sinatra had contact with about ten major hoodlums, some of whom had his unlisted number. As a result, Sinatra has become, in Hamill’s words, “the most investigated American performer since John Wilkes Booth.” The press wanted to see corruption in Sinatra’s connection to the Mob, although none has ever been proved; in any case, it’s not cash but comfort that the Mob really offered Sinatra. In the company of these violent men, he was not judged for his own violent nature; in the context of their ignorance, his lack of education didn’t matter. He could drop the carapace of sophistication and embrace his shadow.
The epigraph to one ofhis daughter’s books about him quotes Sinatra as saying, “Maybe there might be value to a firefly, or an instant-long Roman candle.” Sinatra’s voice, as he well knows, put a lasting glow on six decades of American life and three generations of fans. Sinatra stumped for F.D.R., who invited him to the White House; he was still around to sing at the inaugural gala of Ronald and Nancy Reagan. His was a voice for all political seasons. In the forties, with “The Song Is You,” “All or Nothing at All,” and “I’ll Never Smile Again,” he tranquillized the nation; in the fifties boom, he was the slaphappy sound of good times (“Young at Heart,” “Come Fly with Me,” “Oh! Look at Me Now!”); in the sixties, he ushered in the optimism of the Kennedy era with “All the Way,” “The Best Is Yet to Come,” and “High Hopes”; and even into the eighties Sinatra was singing the tune of the smug, self-aggrandizing Reagan years with “My Way.”
Over all those decades, Sinatra continually struggled to make his sound current. In the sixties, for example, under his own banner at Reprise, he produced a few great albums; at the same time, almost imperceptibly, as popular musical tastes underwent a seismic shift, Sinatra’s records began to deteriorate into pick-up albums—collections of singles, like “That’s Life” and, a particularly lazy effort, “Sinatra’s Sinatra,” in which he just rerecorded his Capitol songs. (This prompted Jonathan Schwartz to joke, “Reprise Records, which Sinatra said stood for ‘to play and play again,’ really stood for ‘to record and record again.’”) Times were changing, and Sinatra had to work to stay fresh. He tried bossa nova with the Brazilian Antonio Carlos Jobim; he mined the jazz seam in collaborations with Duke Ellington and Count Basie, which led to his touring with the Basie band and recording three albums with Basie, including the thrilling live album “Sinatra at the Sands.” By the mid-sixties, however, with the advent of the Beatles and the British invasion, radio stations had been colonized by rock and roll. One night, waiting to go on in Las Vegas, Sinatra looked at the audience and said to Jimmy Van Heusen, beside him, “Look at that. Why won’t they buy the records?” “Of course, they were buying the records by the million,” says Schwartz, to whom Van Heusen told the story. “What he really was saying was ‘Why don’t I have hit singles?’”
Sinatra did have a few brief moments of singles glory in the sixties: “Strangers in the Night,” “That’s Life,” “My Way,” and “Something Stupid,” with his daughter Nancy, which went to No. 1 in the charts in 1967 and became Sinatra’s first gold single. He had long berated rock as “a rancid-smelling aphrodisiac,” but now he tried to cross over and included in his repertoire works by Neil Sedaka, Joni Mitchell, Paul Simon, Stevie Wonder, and the Beatles. “Most of the rock songs Sinatra recorded came out dreadfully,” the music critic John Rockwell writes in “Sinatra.” “With stiff vocal phrasing and, worse, hopelessly anachronistic instrumental arrangements.” He was completely out of synch with the spirit of Mitchell’s “Both Sides Now”; he made a hash of Simon’s “Mrs. Robinson”; and, although he finally got a good arrangement in a second version of George Harrison’s “Something,” he introduced the song for a long time as having been written by John Lennon and Paul McCartney.
He retired briefly in 1971, but by 1973, in response to thirty thousand fan letters and to his own agitated heart, he was back in the studio, and soon afterward he was on the road again. He returned with a new toupee and a gutsy new repertoire. Instead of falling back on his standards, Sinatra learned difficult new songs: “Winners,” “You Will Be My Music,” “There Used to Be a Ballpark,” “Noah,” “Dream Away,” and “Send in the Clowns.” His phrasing was more staccato now, and the bands filled in the spaces. But he had kept faith with his public, and they with him. In 1975, Sinatra took a full-page ad in the L.A. Times, reading, “it was a very good year: countries: 8; cities: 30; attendance: 483,261; total performances: 140; gross: $7,817,473.” Sinatra still had some big innings left: the self-congratulatory best-selling “Trilogy” (1980), and the two multi-platinum “Duets” albums (1993-94), where he sang with contemporary pop stars like Barbra Streisand, Jimmy Buffet, Carly Simon, and Stevie Wonder. Sinatra was still reaching out for a new audience, and he found it, even if the product was well below his high standard. “I’m a belter now, baby,” he was heard to tell the crowd in the late eighties. The last big notes he hit were in “New York, New York.” Schwartz says, “By the eighties, Sinatra was singing knuckleballs.”
At Caesar’s Palace, sometime in the early eighties, Shirley MacLaine caught Sinatra’s show. “I don’t know what was bugging him,” she told me, describing the evening’s first set. “The magic wasn’t there. He marked it. He couldn’t wait to get out.” Afterward, at dinner, Sinatra asked what she thought, and she gave him her version of a pep talk. “Frank, you really ought to remember how you got so many of us through a Second World War, and a New Deal, and gave us an education in music,” she said. “Please don’t just mark it, because it disrespects everything you meant to the whole country. You might seem to some like a ruin but to most of us that ruin is a monument.” MacLaine adds, “His eyes just…It was like nobody had said that to him in a long time.”
In the early nineties, Sinatra began forgetting lyrics. “He’d apologize to the audience,” his pianist Bill Miller says. “They’d say, ‘Hey, Frank we don’t care.’ And they don’t. They want to see him.” Miller goes on, “Then he had second thoughts. You’d see him shaking his head as if to say, ‘I don’t want them feeling sorry for me.’”
Sinatra’s work is his legend; his legend is his work. Not surprisingly, he has eschewed autobiography or an official biography. “There’s too much about my life I’m not proud of,” he says. Inevitably, as children of the famous must, Sinatra’s offspring all claimed their absent father by sustaining some part of his legacy. “You have to do it well,” Nancy says. “You can’t let people piss on it.” She has written two elegantly produced books that are encomiums to the old man; Tina has produced a five-hour TVminiseries of his life story; and Frankie, Jr., who conducted Sinatra’s orchestra, released a CD, “As I Remember It,” in 1996, with new orchestrations of Sinatra standards. Sinatra’s story is hard to keep ideal, filled, as it is, with brigands and barbarity. But as long as he was able Sinatra kept on doing the only kind of penance he knew: singing.
In New York, on Sinatra’s eightieth birthday, the Empire State Building glowed blue for Ole Blue Eyes; on television two days later, Frank and Barbara Sinatra sat like the Sun King and his consort at a front-row table, while behind them L.A.’s Shrine Auditorium was packed to its chandeliers with the rich and famous in evening dress, attending a televised homage to Sinatra and his career. One by one, the grandees of popular American culture came forward to hymn his praises. The first to serenade him was Bruce Springsteen—one New Jersey Boss to another. “My first recollection of Frank’s voice was coming out of a jukebox in a dark bar on a Sunday afternoon, when my mother and I went searching for my father,” Springsteen said before launching into “Angel Eyes.” “And I remember she said, ‘Listen to that, that’s Frank Sinatra. He’s from New Jersey.’ It was a voice filled with bad attitude, life, beauty, excitement, a nasty sense of freedom, sex, and a sad knowledge of the ways of the world. Every song seemed to have as its postscript ‘And if you don’t like it, here’s a punch in the kisser.’” Springsteen continued, “But it was the deep blueness of Frank’s voice that affected me the most, and, while his music became synonymous with black tie, good life, the best booze, women, sophistication, his blues voice was always the sound of hard luck and men late at night with the last ten dollars in their pockets trying to figure a way out. On behalf of all New Jersey, Frank, I want to say, ‘Hail, brother, you sang out our soul.’”
Springsteen had met Sinatra for the first time a few months before that, at Sinatra’s house in Beverly Hills. After supper, the guests gathered around the piano to sing. Among them were Bob Dylan, Steve Lawrence, Eydie Gormé, the singer Patti Scialfa (who is Springsteen’s wife), the producers George Slaughter and Mace Neufeld, and Tita Cahn. “You could feel Frank—you know when a thoroughbred is sort of wired up and is ready to race,” Tita Cahn says. They harmonized for a while, and then someone suggested one of Sammy Cahn’s early hits with Sinatra, “Guess I’ll Hang My Tears Out to Dry.” The group launched in:
When I want rain,
I get sunny weather;
I’m just as blue as the sky,
Since love is gone,
Can’t pull myself together.
Guess I’ll hang my tears out to dry.
“Hold it!” Sinatra interrupted. “You know I sing solo.”
He finished the song alone. ?