Frank Sinatra and Pete Hamill, as products of the same urban landscape, have both been credited with giving the American city a voice. In this widely acclaimed and bestselling appreciation, Hamill draws on his intimate experience of the man and the music to evoke the essence of Sinatra, illuminating the singer’s art and his legend from the point of view of a confidant and a fan.

“As succinct and laconically classy as its title.”

— Adam Woog, Seattle Times

“Hamill’s illuminations are considerable without ever stooping to facile psychologizing. … He does a better job of placing Sinatra’s saga in a social and political context than any of his biographers have. … Why Sinatra Matters is most valuable in its explication of how Sinatra came to formulate a musical style that was a sound track to urban American life.”

— Dan DeLuca, Philadelphia Inquirer

“A graceful reminiscence of Sinatra after hours serves as the frame for shrewd reflections on the singer’s art, his personality, his audience, and — most interesting — his ethnicity, a subject about which Hamill, against all odds, contrives to say fresh and persuasive things.”

— Terry Teachout, New York Times Book Review

“A brief but eloquent homage. … Hamill succeeds — convincingly, with natty aplomb — in explaining why Sinatra, even now, matters.”

— Tom Chaffin, LA Weekly

“A snazzy ode to ‘Ole Blue Eyes.’”

— People

“Compelling reading for anyone with a feeling for the late singer.”

— Adam Woog, Seattle Times

“An engrossing book … sharply evocative.”

— Don Freeman, San Diego Union-Tribune

“Hamill conveys moments with memories so vivid that you can smell the smoke and taste the bourbon.”

— Vicki L. Friedman, Virginian-Pilot

“This is a beautiful thing, an admiring rumination on Sinatra the man, the persona, and the towering talent. … An absolutely terrific work.”

— Liz Smith, Newsday

“Hamill’s illuminations are considerable. … Any Sinatra fan hungry for a fresh take will eat up Why Sinatra Matters.”

— Dan DeLuca, Philadelphia Inquirer

“Even if you think you know why Sinatra matters, this slim biographical essay proves the most intimate and thoughtful eulogy for ‘the Voice’ yet. … Hamill’s concise, eloquent musings leave you wanting not to read a full-blown biography but to listen again to Sinatra’s best songs.”

— Megan Harlan, Entertainment Weekly

“What a perfect match: the world’s greatest ‘saloon singer’ eulogized superbly by the author of A Drinking Life. … Why Sinatra Matters belongs in any collection of important books on American popular music of the 20th century.”

— Kirkus Reviews

“The only thing wrong with this brief but penetrating essay is that it is far too short.”

— Terry Teachout, New York Times Book Review

Novels

A KILLING FOR CHRIST

THE GIFT

DIRTY LAUNDRY

FLESH AND BLOOD

THE DEADLY PIECE

THE GUNS OF HEAVEN

LOVING WOMEN

SNOW IN AUGUST

Short Story Collections

THE INVISIBLE CITY

TOKYO SKETCHES

Journalism

IRRATIONAL RAVINGS

PIECEWORK

NEWS IS A VERB

Memoir

A DRINKING LIFE

WHEN FRANK SINATRA died on the evening of May 14, 1998, the news made the front pages of newspapers all over the world. Many ran extra editions and followed with special supplements. There was little sense of shock; he had been a long time dying. He had also been a long time living, and so the obituaries were full of his life and times.

It was mandatory to chronicle his wins and losses, his four marriages, his battles, verbal and physical, with reporters and photographers. His romances required many inches of type. There were accounts of his fierce temper, his brutalities, his drunken cruelties. Some described him as a thug or a monster, whose behavior was redeemed only by his talent. We read brief charts of his political odyssey from left to right. The shadow cast upon him by the Mob was also an inevitable part of the stories. And there were tales of his personal generosity to friends and strangers and the millions of dollars he had raised for charities. He was clearly a complicated man.

“Being an eighteen-karat manic depressive,” he was quoted in many of the obituaries, “and having lived a life of violent emotional contradictions, I have perhaps an overacute capacity for sadness and elation.”

But much of the language of farewell had a stale, even hollow quality, probably because most of the obituaries had been ready for too many months. Sinatra had been a virtual recluse since 1995, making only rare public appearances. Over the previous year he had been in and out of hospitals. There were reports from California that he had suffered several heart attacks and, with the possible onset of Alzheimer’s, had difficulty recognizing even old friends. Across those final months there was little hard news about his condition; his children insisted he was fine, although cranky and cantankerous, and so the vacuum was filled with rumor and supposition. The truth was probably a simple one. Frank Sinatra, after a life in which too many cigarettes and too much whiskey were part of the deal, was old; and as happens to all of us when we grow old, the parts just broke down. He had abused his body in a way that was special to his generation of American men; that he had survived until eighty-two was itself a kind of triumph over the odds.

There were some peculiar components to the television coverage. Most of it was narrated by people from a much younger generation; as they mouthed words about loss and farewell, the tone had an odd insincerity — they could have been discussing someone from the nineteenth century. They were also prisoners of existing visual images. We saw Sinatra at different ages: a very young Sinatra in bow tie and padded shoulders when he was The Voice; a drawn, emaciated Sinatra, flaring at photographers or wearing a thin, pimplike mustache, during his time with Ava Gardner; Sinatra as Maggio in From Here to Eternity and a grinning Sinatra receiving his Academy Award afterward; clips from his television shows, including a bizarre image of Sinatra standing on two chairs, one foot on each, while singing “I’ve Got the World on a String”; Sinatra with the Rat Pack, horsing around on the stages of Las Vegas; Sinatra with various presidents, from Roosevelt to Reagan; and, of course, endless versions of “My Way.”

It was difficult, reading and watching all of this, to remember why Sinatra mattered to so many people, and why he will continue to matter in the years ahead. The radio did a much better job than print or television, because on radio we heard the music. Not abrupt fragments of songs, not clipped, impatient digests. Late at night, driving through a great city, moving on the dark streets of New York or Paris, Tokyo or London, you could connect more directly to what truly mattered: the music.

The music was the engine of the life. If there had been no music, there would have been no immense obituaries and no televised farewells. To be sure, Sinatra was one of those figures whose art is often overshadowed by the life. In the end, it is of minor interest that Lord Byron swam the Hellespont, that André Malraux flew in combat during the Spanish Civil War, or that Ernest Hemingway shot lions in Africa. In the end, only the work matters. Sinatra’s finest work was making music.

Sinatra, however, did matter in other ways. He wasn’t simply an entertainer from a specific time and place in American life who lived on as a kind of musty artifact. Through a combination of artistic originality, great passion, and immense will, he transcended several eras and indirectly helped change the way all of us lived. He was formed by an America that is long gone: the country of the European immigrants and the virulent America-for-Americans nativism that was directed at them; the country in which a mindless Puritanism, allied with that scapegoating nativism, imposed Prohibition upon the land and helped create the Mob; a country undergoing a vast transformation from a fundamentally rural society to one dominated by cities; a country that passed through Depression and war into the uncertain realities of peace. They were extraordinary times, and in his own way, driven by his own confusions, neuroses, angers, and ambitions, Frank Sinatra helped push the country forward.

This book is about the accomplishments of Frank Sinatra and why he matters. Some of it is personal, because for a while, I was friendly with Sinatra, talked with him in saloons, in Las Vegas, even for a few days one year in Monte Carlo. At one point he wanted me to write his autobiography; it never happened, for reasons that are no longer important. But in the course of discussing his life, he talked about himself in ways that still had an element of wonder to them; part of him still could not believe that he had become the legend he was. To be sure, we were not friends in any conventional way; I did not visit his home and he did not visit mine. Only a very few intimate friends ever had such access, and I was certainly not one of them. But I liked him enormously.

THIS WAS ON A NEW YORK midnight in 1970. A hard spring rain had emptied Third Avenue, and neon lights scribbled garishly across the glistening black asphalt. From the front window of P. J. Clarke’s saloon, you could see a few taxis cruising slowly among the spokes of ruined umbrellas and a trash basket lying on its side, its contents turning to pulp. Across the street, two old rummies huddled in the doorway of an antique store.

On this night in the rain-drowned city, we were safe and dry at an oak table in the back room of the saloon. Clarke’s was, and remains, a place out of another time, all burnished wood and chased mirrors, Irish flags and browning photographs of prizefighters. A few aging men at the long, bright bar could gaze out the windows and still see the Third Avenue El, gone since 1955, or the Irish tenements that were smashed into rubble and replaced with steel-and-glass office buildings. They were each drinking alone and looked as if they remembered other nights too, evoked by the music of the jukebox.

The man singing for the lonesome men at the bar was at our table. Or more precisely, we were at his table. Anytime Frank Sinatra sat down at a table, it became his table. On this night he was in New York for a concert and he was in good spirits. To begin with, the hands of the clock had passed twelve, and he was in a large city, specifically the hard, wounded metropolis of New York. For decades now, Sinatra had defined the glamour of the urban night. It was both a time and a place; to inhabit the night, to be one of its restless creatures, was a small act of defiance, a shared declaration of freedom, a refusal to play by all those conventional rules that insisted on men and women rising at seven in the morning, leaving for work at eight, and falling exhausted into bed at ten o’clock that night. In his music, Sinatra gave voice to all those who believed that the most intense living begins at midnight: show people, bartenders, and sporting women; gamblers, detectives, and gangsters; small winners and big losers; artists and newspapermen. If you loved someone who did not love you back, you could always walk into a saloon, put your money on the bar, and listen to Sinatra.

Here in one of the late-night places of an all-night city, Sinatra was wearing a dark suit, a perfectly knotted red tie, a pale blue shirt, silver cuff links, and was drinking Jack Daniel’s. He was still lean then. The famous face remained an arrangement of knobs and planes that didn’t assemble into any conventional version of masculine handsomeness but had an enormous vitality; it was a face that defeated painters and seduced photographers. His eyes were bright and blue (although nobody had yet called him Old Blue Eyes), and the mouth was mobile and expressive. He had a wonderful smile. The voice, of course, was a whiskey-and-cigarettes baritone.

He sat with his back against the wall in the muted light of the room and seemed to ignore his own voice on the jukebox. He was facing Danny Lavezzo, who ran Clarke’s; William B. Williams, the disc jockey who had christened Sinatra “the Chairman of the Board”; Jilly Bizzo, who ran a saloon across town and had been one of Sinatra’s best friends for more than twenty years; two young women whose faces were too perfect; and the sportswriter Jimmy Cannon. The table was crowded with glasses, ashtrays, bowls of peanuts and pretzels. Only Cannon sipped coffee. There were about eight other people at smaller tables, and you could see the rain racing down one of the small side windows. Lavezzo made certain the other customers were kept at a distance by seating them as far from Sinatra’s table as possible without handing them umbrellas. The sound of “When Your Lover Has Gone” made Cannon turn his head toward the jukebox.

“That’s the saddest goddamned song ever written,” he said.

“It’s right up there,” Sinatra said, shaking his head and lighting an unfiltered Camel with a heavy silver lighter.

“You know where it’s from?” Cannon said. “It’s from a terrible movie called Blonde Crazy. Cagney and Joanie. 1931.”

“Joanie who?” said Jilly Rizzo, his bad eye gleaming. “Crawford?”

“Blondell, dummy,” Sinatra said. “Joan Blondell. Cannon used to go with her.”

“You’re kidding me,” Rizzo said. “You went with Joan Blondell? A busted-down sportswriter went out with Joan Blondell?”

“He didn’t always look this bad,” Sinatra said. Cannon smiled in an embarrassed way. He was a small man with a long, pudgy Irish face and horn-rimmed glasses.

“It was a long time ago,” Cannon said. He looked relieved when the song ended, but its lonesome mood seemed to stain the air around him.

Rizzo turned to one of the young women. “You ever hear of Joan Blondell?”

The young woman shrugged. No.

“What about Cagney? You know, James Cagney?”

“I know him,” said the second woman brightly. “He was the guy, the captain, in that picture with Henry Fonda, right? About the navy?”

“You win a dish of strawberries, sweetheart,” Sinatra said.

“I don’t like strawberries,” she said in a baffled way. Sinatra laughed out loud. So did the rest of us, but it wasn’t until I was home, hours later, that I realized Sinatra had mixed up the strawberries scene from The Caine Mutiny with the potted palm scene from Mister Roberts. We’d all laughed with him, but the young woman was right to be baffled.

After a while Rizzo got up to take the two young women to a taxi while the conversation roamed in other directions. Somehow it arrived at writers. Was Ernest Hemingway greater than F. Scott Fitzgerald? Cannon insisted on the superiority of Hemingway. Sinatra preferred Fitzgerald.

“That Great Gatsby, come on, Jimmy, Hemingway couldn’t do that.”

“Yeah, but he could do a lot of other things,” Cannon said. “And Fitzgerald could only do that one thing.”

Rizzo returned and sat down. Cannon turned to me, the only other writer at the table: “What do you think?”

I repeated something Dizzy Gillespie once told me in an interview: “The professional is the guy that can do it twice.”

“Wow, is that true,” Sinatra said. “About everything. That’s a great line.”

“Yeah, and it’s a vote for Hemingway,” Cannon said. On the jukebox, Sinatra was singing “You Make Me Feel So Young.”

“What about you, Jilly? Hemingway or Fitzgerald?”

“Hey, no contest,” Jilly said, deadpan. “Ella all the way.”

They all laughed, and then the talk shifted, and “Don’t Worry ’Bout Me” was on the juke, and the waiter brought another round and clean ashtrays. Someone wanted to know the name of the worst living American. The nominations flowed and ebbed: Walter O’Malley, Mitch Miller, Richard Nixon (“Come on, lay off,” said Sinatra, who had supported Nixon over George McGovern). But then another name was offered and in a rush of enthusiasm, the table unanimously voted the title of worst living American to the boxer Jake La Motta.

“He dumped the fight to Billy Fox, and never told his father, who bet his life savings on Jake,” Sinatra said. “Lower than whale shit.”

And from La Motta, they moved seamlessly to Sugar Ray Robinson, another creature of the New York night. During the Depression Robinson had come down from Harlem to dance for pennies in the doorways of Times Square. Then he had become a fighter of extraordinary grace and power. He had owned a couple of apartment houses in Harlem, a lavender Cadillac, a bar called Sugar Ray’s, where women arrived each night to find him, and then lost them all. An accountant took all of Robinson’s money to the racetrack, and the fighter had to go back to a sport he no longer loved. Still, he had fought La Motta six times, winning five, including a thirteenth-round knockout that gave him the middleweight championship in a brutal fight in Chicago in 1951. In the fighter’s great days, Cannon and Robinson had been close; we didn’t know it that night, but Sinatra had privately arranged to support Robinson after the old champion moved to California. They all knew him.

“He used to come in here all the time,” Lavezzo said. “He was some beautiful-looking guy.” I had seen Robinson’s fierce 1957 war with Carmen Basilio, watched him a lot in the old Stillman’s Gym, and had covered Robinson’s sad last fight, a loss to Joey Archer in 1965 when Sugar Ray was forty-four. Sinatra remembered seeing Robinson knock out Jackie Wilson in Los Angeles in 1947. “You couldn’t believe it,” he said. “The hand speed, the power, the fucking elegance.” Jilly saw him decision Kid Gavilan in New York in 1948, and Williams and Lavezzo recalled specific rounds from the two fights with Basilio and the one-punch knockout of Gene Fullmer in the spring of ’57. They all talked with a kind of reverence.

“What was it the guy said?” Sinatra said. “There was Ray Robinson, and then there was the top ten.”

There was something else floating around in the talk about Robinson. They were all from the same generation, and Robinson symbolized that generation in the same way that Sinatra did. Nobody said so at the table in Clarke’s, but they knew it. If Sinatra had not been there (for ass-kissing was not part of the style), someone would have said, There’s Sinatra, and then there’s the top ten.

Suddenly, Sinatra rose from his seat, excusing himself. A few other patrons looked at him. A woman in her forties widened her eyes and whispered across the table to her man, who turned for a glance. Lavezzo tensed; Clarke’s was not the sort of place that encouraged customers to ask for autographs. From the speakers, Sinatra’s exuberant voice was now singing “I’ve Got the World on a String.” He was telling the world that he could make the rain go.

“Hey, Danny, don’t you have anything on the jukebox besides this dago kid?” Sinatra said to Lavezzo. The saloonkeeper laughed and got up too. Sinatra led the way into a narrow passageway that opened into the front room. A large unsmiling man rose from a small table and followed them. In Clarke’s, Sinatra didn’t need directions to get to the john.

“He looks good, Jilly,” Cannon said.

“Better than ever,” Jilly said.

“I wish he’d give up the goddamned Camels,” Williams said.

“That’s like asking him to give up broads,” Jilly said.

“He should give up marrying broads,” said Cannon, a lifelong bachelor.

There was another voice on the jukebox now. Billie Holiday. She was singing “Mean to Me” in the scraped, hurt voice of her last years. From the Ray Ellis album with strings. Lady in Satin.

“This album always makes me want to cry,” Williams said.

“Just don’t cry into the whiskey,” Rizzo said. “Makes it too salty.” Cannon smiled. He’d given up whiskey in the 1940s but never gave up the night shift. Whiskey was a big part of nights in that city, and he knew it was futile to deliver sermons to his friends.

“What makes you cry, Jilly?” Cannon asked.

“Poverty,” Jilly answered. And he laughed out loud.

Then Sinatra was coming back through the passageway, with the large dour man guarding his back. Two young women stared from the far end of the passage, giggling and tentative, as if having a small debate, and then turned back.

“You know what I love most about this joint?” Sinatra said. “Taking a piss. Those urinals … You could stand Abe Beame in one of them and have room to spare.”

“The really great thing is the ice at the bottom,” Cannon said. “It’s like drilling a tunnel.”

“That’s power,” Sinatra said, laughing, reaching for the Camels. Lavezzo returned, looking as if he’d just flown a combat mission.

“That better?” he said, gesturing toward the unseen speakers and the anguished voice of Lady Day.

“Like fine wine,” Sinatra said, allowing smoke to leak from his mouth. I glanced at my watch. 2:25, the rain still falling. Cannon sipped his coffee. Jilly smothered a yawn. Then Billie Holiday began to sing “I’m a Fool to Want You.” A song out of Sinatra’s past. Out of 1951 and Ava Gardner and the most terrible time of his life. Everybody at the table knew the story. Sinatra stared for a beat at the bourbon in his glass. Then shook his head.

“Time to go,” he said.

We all rose and went to the side door and followed Frank Sinatra into the night.

THE LIFE AND CAREER of Frank Sinatra are inseparable from the most powerful of all modern American myths: the saga of immigration. Because he was the son of immigrants, his success thrilled millions who were products of the same rough history. Through the power of his art and his personality, he became one of a very small group that would permanently shift the image of Italian Americans. Many aspects of his character were shaped by that immigrant experience, which often fueled his notorious volatility. More important, it infused his art.

“Of course, it meant something to me to be the son of immigrants,” Sinatra said to me once. “How could it not? How the hell could it not? I grew up for a few years thinking I was just another American kid. Then I discovered at — what? five? six? — I discovered that some people thought I was a dago. A wop. A guinea.” An angry pause. “You know, like I didn’t have a fucking name.” An angrier pause. “That’s why years later, when Harry [James] wanted me to change my name, I said no way, baby. The name is Sinatra. Frank fucking Sinatra.”

He grew up in a time when the wounds caused by nativism and anti-Italian bigotry were still raw. Those wounds, and the scar tissue they left behind, affected the way millions of Italian Americans lived, what they talked about, even how they chose to read the newspapers. In the years of his childhood, Sinatra was no exception.

“Growing up, I would hear the stories,” he said to me once. “Things that happened, because you were Italian. … I don’t mean it was the only thing people talked about. That would be a lie. But the stories were there. The warnings, the prejudice. You heard about it at home, in the barbershop, on the corner. You never heard about it in school. But it was there. Later, I heard the same kinds of things from my Jewish friends, how they learned about the ways they could get in trouble. Always the same old shit.”

The stories were about insults, exploitation, worse. Part of the trouble was caused by sheer numbers. From 1880 to the beginning of World War I, more than 24 million Europeans crossed the Atlantic to America. About 4.5 million were Italians, 80 percent of them fleeing the exhausted hills and emptying villages of II Mezzogiorno, the neglected provinces of southern Italy and Sicily. Many thousands went to Brazil. Another million journeyed to Argentina and permanently transformed the character of that nation. The vast majority came to the United States. At first, the more adventurous Italians moved west, helping build thousands of miles of railroad tracks, finding jobs as fishermen on the sunny coasts of California or developing that state’s lush vineyards. Most settled in cities.

“I read a book once about how the Irish when they came to America never wanted to be farmers again,” Sinatra said. “I guess if you work on a farm and everything dies in the ground, you don’t ever trust the ground again. The Italians were like that too.”

Rural Italian and Irish immigrants shared that common grievance against the Old Country: the exhausted or poisoned land had failed them and, in a way, betrayed their faith and prayers; in the New World, they sought the solace of cities. Cement was better than hunger; a job and a lock on the door provided the only true safety. The Jews, haunted by the brutal realities of recurrent pogroms, or disenfranchised by a crippling, pervasive anti-Semitism, were drawn by the even brighter promise of freedom; no matter how terrible life might be in the slums of the Lower East Side, the Cossacks would not arrive at dawn with their sabers drawn. The Irish, Italian, and Eastern European Jewish immigrants shared a suspicion of government and the police that helped form the style of the American cities where they settled. Their children were touched, in various degrees, by their Old Country lore and their nostalgias. Many of Frank Sinatra’s attitudes came from that mixture.

But in the last years of the nineteenth century, rural Italians faced some special problems in urban America, burdens that did not afflict the Irish and the Jews in the same way. Even in the Italian language, too many immigrants could not read or write. Depending upon the year, between 50 and 70 percent of the new arrivals were illiterate. This was a severe handicap in the booming, more complex cities of the United States and forced many into manual labor or trades that did not demand book learning. Four thousand Italian immigrants found work building the New York subways. Others labored in the building trades, helping erect the soaring monuments of twentieth-century New York. Many worked as barbers or seamstresses, as blacksmiths or mechanics or stone-masons. Some were chefs or bakers. Others were fruit and vegetable peddlers, bootblacks, or shoemakers. A few created an instant stereotype: the organ grinder. These small mustached men moved through many neighborhoods, equipped with hand organs, an occasional monkey, and a cup for coins. For most people the organ grinder was a passing amusement, singing “O Sole Mio” into the humid air of a Saturday morning; for many Italian Americans, the organ grinder was a humiliation, a beggar with a monkey and a voice.

Most of the time, the Italians did their work with silent courage and little public complaint. If you came from a place where there were never enough jobs, work itself was a kind of triumph. For those immigrants, there was no such thing as a meaningless job; the job itself was the meaning.

“They did whatever the hell they had to do to put food on the table,” Sinatra said to me once. “They took any kind of dumb job, and you know why? So their kids wouldn’t have to do those jobs. So you wouldn’t have to do it. So I wouldn’t have to do it. They were some kind of people.”

The Italians also had to undergo another peculiarly American rite of passage: they had to endure and then confront the ferocious bigotry of those who had come before them. This was compounded by the American obsession with race. At the peak of the migration, there were millions of African Americans still alive who had lived as slaves; political compromise was leading to an iron segregation in the American South; various hare-brained race theorists spent their time sniffing out hidden racial strains in individuals. Guilt over slavery, and over the partial extermination of American Indians, created self-serving notions about the inferiority of those with darker skin. Along came the Italians. The majority of Italian immigrants were Sicilians, from an island where Arab and Spanish conquerors had been dominant for centuries. The glories of those civilizations meant nothing to many older Americans; the darker complexions of the Mediterranean were suspect among those who believed that Americans were supposed to be fair-skinned. The coarse, hurting language of ethnic inferiority followed, and it affected Frank Sinatra. Even in the years of his fame and power, Sinatra could not completely insulate himself from the social cruelties of that process.

“Every once in a while,” he told me, “I’d be at a party somewhere, in Hollywood or New York or wherever, and it would be very civilized, you know, black tie, the best crystal, all of that. And I’d see a guy staring at me from the corner of the room, and I knew what word was in his head. The word was guinea.”

Some of this social minefield was waiting for the Italians when they got off the boat at Castle Garden or Ellis Island. In the 1890s, when Frank Sinatra’s grandparents made their separate passages from Italy, carrying with them the children who would become his parents, a renewed nativist fever was surging through the United States. It was driven, of course, by fear. A fear of Catholics, a fear of Jews, a fear of strange languages and secret societies, a fear of race, a fear of People Who Are Not Like Us. The Irish had gone through this paranoid test for the half century following the Great Famine that sent them to America. For a shorter period of time, the Jews who arrived on the same great immigrant tide as the Italians would suffer similar humiliations. Mexicans, Dominicans, and many Asians are today objects of the same collective stupidity. For the Italians and their children, this brutal ritual would last much longer than for other groups. And a hundred years ago it was not a simple matter of manners, social slights, or bigoted jokes. It could be a matter of life and death.

“Guys my age, one reason they didn’t pay much attention to school was the schools didn’t tell stories we knew,” Sinatra said. “We heard what had happened in different places. We didn’t get it from school.”

One story that Sinatra heard was about an event that happened about the time his parents and grandparents arrived in the United States. In 1891 a singular atrocity took place in New Orleans that drastically altered the situation of all Italian Americans. A group of Italian immigrants were accused of murdering a corrupt police superintendent named David Hennessy. Nineteen were charged with the crime; eleven were tried for murder. There was much lurid talk in the newspapers of the day about the Black Hand, a secret gang of Sicilians dedicated to crime. Then, for the first time, many Americans heard the word Mafia. This was even bigger than the Black Hand. The Mafia myth, which conferred immense hidden powers to a relative handful of hoodlums, was born. It didn’t matter that among the 4.5 million Italian immigrants, no more than a few thousand were connected to the Honored Society; it didn’t matter that in the prisons of New York, the Italians were a tiny minority among an army of Irish lawbreakers. The myth had been spawned in New Orleans. Spreading like a stain, inflated by novels and movies and a cottage industry of hysterical politicians and prosecutors, the dark myth would affect all Italian Americans; it would directly affect the life of Frank Sinatra.

“Half the troubles I’ve had,” he said once, “were because my name ended in a vowel. They tried to put me together with all the other stuff that happened. I wasn’t the only one. But there I was, up on a goddamned stage. I was pretty easy to see, a good target.”

In New Orleans the garish myth flowered in the imaginations of newspapermen. There were gangsters among us, the newspapers said, who were different from Irish gangsters or American gangsters; they were darker, swarthier, spoke a different language, and were bound together by blood oaths! In largely Catholic New Orleans, famous for its easy, tolerant ways, the myth had crude power; paranoia usually does. Even among some supporters of the Irish Republican Brotherhood, a secret society if there ever was one, it was believed that the Italians were different. The IRB wanted freedom for Ireland; the Mafia wanted America!

But then a strange thing happened in the New Orleans trial of the Italian immigrants for the murder of David Hennessy: the jury acquitted eight of the men and reached no verdict on the other three. The evidence simply wasn’t there. Not about this specific murder. And not about the Mafia.

That verdict did not satisfy the respectable Americans of New Orleans. They claimed the fix was in. They claimed that the shadowy Italian organization had paid off the jurors. Two days after the verdicts a mob of several thousand, led by sixty leading citizens and including a small number of African Americans, surrounded the jail where the Italians were awaiting final bureaucratic disposition of their cases. The Americans stormed the jail, dragged the Italians out of their cells, and murdered them. Two were hanged screaming from lampposts. One of them tried climbing the hangman’s rope with his free hands and was riddled with bullets. Seven were executed by firing squads in the yard of the jail. Two crawled into a prison doghouse to hide from the mob, were discovered, and were shot to pieces. It remains the worst single lynching in American history.

“When I was young,” Frank Sinatra said when he was in his sixties, “people used to ask me why I sent money to the NAACP and, you know, tried to help, in my own small way. I used to say, Because we’ve been there too, man. It wasn’t just black people hanging from the end of those fucking ropes.”

The story of the New Orleans outrage spread swiftly through the world of the Italian immigrant in America, underlined by the decision of the Italian government to withdraw its ambassador in protest. Mainstream America didn’t express much horror. According to Professor Richard Gambino, in his book Vendetta, the lynchings were approved by the editorial writers of the New York Times, Washington Post, St. Louis Globe-Democrat, and San Francisco Chronicle, along with about 50 percent of the other newspapers in the nation. Theodore Roosevelt, one of the leading younger Republicans, said the lynchings were “a rather good thing” and bragged that he had said so at a party to “various dago diplomats.”

“Maybe that’s why so many people didn’t trust the newspapers, even if they could read them,” Sinatra said, almost eighty years later. Then he laughed. “Maybe it’s why I did so many dumb things with newspapermen too.”

The message from New Orleans was clear to the immigrants. Americans didn’t like Italians. An American was supposed to be white, Anglo-Saxon, and Protestant. He was supposed to come from northern Europe. Yes, the Americans talked big about democracy and equality and the virtues of hard work; but in reality, the game was rigged. In the aftermath of the New Orleans lynchings, a grand jury couldn’t find enough evidence to indict the murderers, in spite of the presence of hundreds of eyewitnesses. Instead, the grand jurors indicted six men who worked for the defense attorneys, charging them with jury tampering. This chilling illustration of the failure of the American criminal justice system was part of a wider pattern. There were anti-Italian murders in the Midwest and barn burnings on the property of Italian farmers in the American South. Men from the drought-stricken fields of Sicily and Calabria were in awe of the rich earth of La America, but too often they were driven off that land by night riders. It was no surprise that many of those once-optimistic and naive Italians sought refuge in the cities. And no surprise that their ghettos became fortresses, where only one social unit mattered: the family. Nobody else could be trusted, up to and including the president of the United States.

In such places the Mafia did begin to establish itself, usually victimizing Italians but bringing a kind of authority to the social structure of the ghetto. If the government treated you with contempt or suspicion, if trade unions rejected you, if at last your children had a chance for an education and the teachers made fun of them, then you would have to live by your own rules, or pack up and leave. In fact, hundreds of thousands of Italians did go home, many of them embittered by their American experience. For them, the promises implied by the Statue of Liberty were part of a cruel joke; more Italian immigrants returned home than any other nationality.

But millions stayed on, seeking their own means of protection within the warm fortress of the family and its extension, the ghetto. If, in the pursuit of justice or progress they could not depend upon the police or the courts, if they could not obtain loans from the banks, then they would go to the man in the white suit from Francis Ford Coppola’s version of The Godfather, the agent of the Honored Society. He could arrange for extortionary loans. He could settle disputes. He could dispense rough justice. Always at a price, of course. In cash, or in obligations. During the years before World War I, he was a parochial figure, strictly local, an exotic import, a poisonous flower unique to the closed ghetto hothouse. But he was created by an American failure. More than anything else, he emphasized how cut off many Italian immigrants were from the larger American society.

This isolation, this shared solitude, created problems that took generations to solve. Education was often sneered at; what was the use of working hard in school if you couldn’t take a diploma into a good job? “I know a guy went to college,” I would hear from my Italian American friends growing up in Brooklyn. “He’s driving a truck.” Many would retreat into passivity, keeping their heads down, getting through a life in silence and safety. Others would try to defuse potential danger by performing the public role of caricatured Italian Americans, the organ grinder, the fruit peddler, a Mediterranean variation on the earlier role of the Stage Irishman.

“You know what radio show I hated the most?” Sinatra would say, many years later. “It was called Life with Luigi, with J. Carrol Naish — there’s a good Italian name for you — and it was all about Italians who spoke like-a-dis, and worried about ladies who squeeze-a da tomatoes on-a da fruit stand. The terrible thing was, it made me laugh. Because it did have some truth to it. We all knew guys like that growing up. But then I would hate myself for laughing at the goddamned thing.”

This is certain: many of the older people among whom Frank Sinatra grew up in Hoboken were shaped by the stark conflict between what America promised and what America delivered. Such a conflict can lead to the development of a defensive style, the adoption of masks of cynicism or irony, or some merger of both. Or it can lead to the guise of the don’t-fuck-with-me tough guy. At different times Sinatra would try on all the masks.

“Sometimes with me, it was a case of if-you-got-the-name-you-might-as-well-have-the-game,” he said to me once. “You think I’m just some wop wise guy off the street? All right, I’ll be a wop wise guy off the street and break your fucking head.”

As an artist, Sinatra had only one basic subject: loneliness. His ballads are all strategies for dealing with loneliness; his up-tempo performances are expressions of release from that loneliness. The former are almost all fueled by abandonment, odes to the girl who got away. The up-tempo tunes embrace the girl who has just arrived. Across his long career, Sinatra did many variations on this basic theme, but he got into real trouble only when he strayed from that essentially urban feeling of being the lone man in the crowded city. He is at his most ludicrous in the film clip where he sings “Ol’ Man River” in a white tuxedo; he is at his most self-parodic in the part of the Trilogy album when he addresses a hymn to himself while a celestial background choir chants, “Sinatra! Sinatra!” Like all great stars, he was susceptible to the twin temptations of flattery and mythomania. But in the end, his finest work takes place at the midnight hour, when he tells the bartender that it’s a quarter to three and there’s no one in the place except you and me.

There could have been no other subject, of course, if Sinatra was to draw, like any major artist, on the emotions that he felt most deeply. Frank Sinatra was the first and only child of Dolly Sinatra. After the panic, horror, and physical damage of her son’s birth, she was unable to bear any more children. So Frank grew up as a lone child in a neighborhood of large families. That special condition was to mark his psyche as surely as the doctor’s forceps marked his face.

“I used to wish I had an older brother that could help me when I needed him,” he said. “I wished I had a younger sister I could protect. But I didn’t. It was Dolly, Marty, and me.”

The first child in immigrant families is also the first American, the one who truly begins the American part of the family saga. But an only child is in a position of greater isolation than most such children; he or she has no older brothers and sisters who can serve as guides; there are no younger siblings who can benefit from hard-earned knowledge. The American child is forced to tell what he knows to strangers. That is, he must go beyond the older people in his life, and find an audience. And he (or she) must find ways to deal with the deepest loneliness: the hours after the audience is gone and the boy closes the door to his room.

“There’s nothing worse when you are a kid than lying there in the dark,” he said to me once. “You got a million things in your head and nobody to tell them to.”

Frank Sinatra’s personal solitude was compounded by the nature of his parents. His father lived much of his life in a dark pool of silence. “He was a nice guy,” Sinatra said later. “I loved him. But the man was the loneliest guy I ever knew.” The boy also must have been uneasy trying to separate his father, Marty Sinatra, from the public person called Marty O’Brien. A private Italian and a public Irishman. A man who was alone at a kitchen table but known publicly to dozens of people on the street. In those days it would not have been strange for a boy to believe that the man was ashamed of being Italian. His father’s split identity surely explains, at least in part, Sinatra’s later vehemence about keeping his own name when Harry James wanted to change it.

“He wanted me to call myself Frankie Satin!” he remembered many decades later, chuckling as he spoke. “Can you imagine? Is that a name or is that a name? Now playing in the lounge, ladies and gennulmen, the one an’ only Frankie Satin. … If I’d’ve done that, I’d be working cruise ships today.” He laughed, and then turned serious. “Besides, one fake name in the family was enough.”

The boy (who was, by the way, christened Frank, not Francis Albert, at St. Francis Roman Catholic Church in Hoboken on April 2, 1916) also had to deal with the absence of Dolly Sinatra. She lived at home and was house proud, but she was gone throughout most of the day, working at a chocolate shop, leaving the boy Frank in the care of his grandmother, Rosa Garavente. In the evenings Dolly’s energies were increasingly absorbed by the duties and rewards of local politics.

She was a Democrat, of course, because the Republicans then, as now, were believed to be anti-immigrant but also because in that part of New Jersey, Democrats had power. She eventually became the leader of the Third Ward in Hoboken’s Ninth District, able to deliver a minimum of six hundred votes to the Hudson County machine run by Boss Hague. To such political activists, ideology was much less important than the practical benefits that came from belonging to a powerful group. You could reward your friends. You could punish your enemies. Or at least hold them back. For many Italians and their children, holding off enemies was a serious matter. By the time Frank Sinatra was ten, there were millions of Ku Klux Klan members across the nation, 40,000 in New Jersey alone; a Klan branch even operated in Hoboken, under the leadership of King Kleagle George P. Apgar, and the haters in the white sheets made no secret of their contempt for Italians. Through politics, Dolly could enlist the law on the side of the Italians in her ward. But even before issues of common defense, she was absorbed with the more mundane concerns of her vocation: the granting of favors. I mentioned once to Sinatra the saying of Boss Tweed: “It’s better to know the judge than to know the law.”

“That could’ve been my mother talking,” he said, and shook his head in a fond way. Alas, knowing the judge didn’t help Dolly when one of her brothers was arrested in 1921 for his part in an armed robbery that left a Railway Express worker dead. He wasn’t the shooter, but he drove the getaway car and was sentenced to ten to fifteen years at hard labor. It could have been worse; he could have been executed.

Even though she was seldom around, Dolly would be a permanent force in her son’s life. As a very young child, Sinatra was often dressed as a girl; Dolly had wanted a girl, bought clothes for a girl, and wasn’t going to waste them. As he grew older, she dressed him with pretensions toward elegance. It was necessary to honor the tradition of la bella figura, dressing as a form of show. There is a studio photograph of the boy at about age five, in full formal dress, with a four-in-hand white bow tie and a carnation pinned to his lapel. He is holding a top hat, one hand resting casually on the seat of a studio chair. His face is both intelligent and tentative, absorbed in the process of the photograph, looking warily at something, or someone, slightly to the left of the photographer. Probably it was Dolly Sinatra. Probably she was giving him stage directions. The photograph, after all, was not for him. It was for her.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“The first thing he said was, ‘Yes, I remember that day when you couldn’t get out those words.’”

Dorsey signed him to a long-term contract for $125 a week, which Sinatra needed since Nancy was now pregnant with their first child. But it wasn’t easy to leave Harry James. The handsome, mustached trumpet player also had a contract with Sinatra, but he was a decent man; he knew his own band wasn’t making money and that Dorsey, a “rich” band, could pay the young singer steadily and well. He tore up his contract and wished Sinatra all the luck in the world. They were still friends when James died in 1983.

“That night the bus pulled out with the rest of the boys at about half-past midnight,” Sinatra later told Douglas-Home. “I’d said goodbye to them all, and it was snowing, I remember. There was nobody around and I stood alone with my suitcase in the snow and watched the taillights disappear. Then the tears started and I tried to run after the bus.”

He didn’t catch it. The James band went to play a gig in Hartford, and Sinatra took a train to New York. From there he went off to three years of school at Dorsey University. Every night he listened to, and learned from, some of the best musicians in the country: pianist Joe Bushkin, drummer Buddy Rich, Berigan and his replacement as lead trumpet, Ziggy Elman (a defector from the Goodman band). Sy Oliver taught Sinatra how to ride or glide over the rhythm base of a tune, not repeat it in his vocals, which was a kind of musical redundancy. Like Sinatra, these musicians had all been formed by Prohibition and the Depression, and the new vocalist liked their style. They were hard-drinking, tough-talking, and dedicated to the music. They smoked cigarettes. They chased women. They gambled. They cursed. And they played at the top of their talent, or were sent packing by the remorseless Dorsey.

Sinatra started as one of the Pied Pipers, the band’s singing group, whose female star was Jo Stafford. She later remembered Sinatra, walking on stage for the first time, as “a very young, slim figure with more hair than he needed. We were all sitting back — like, ‘Oh, yeah, who are you?’ Then he began to sing.” After four bars Stafford knew that she had better listen closely. She thought, “Wow! This is an absolutely new, unique sound.” As she elaborated later: “Nobody had ever sounded like that. In those days most male singers’ biggest thing was to try and sound as much like Bing as possible. Well, he didn’t sound anything like Bing. He didn’t sound like anybody else that I had ever heard.”

Sinatra swiftly gained the respect of the other members of the band, even those who were friends of the departed Jack Leonard. He had a variety of troubles with Buddy Rich, a loner who considered himself the band’s feature attraction, with some reason (many consider him the greatest white drummer of the century). Sinatra even heaved a water pitcher at Rich backstage, sending shards of broken glass scattering and splashing Stafford. But they were also friends, rooming together on the road, where Sinatra would absorb Rich’s knowledge of rhythm and tempo. As his confidence grew, Sinatra strengthened and refined his technique by listening to all the musicians, but above all to Dorsey. And he made records with the band. The first two were recorded on February 1, 1940 (“The Sky Fell Down” and “Too Romantic”); eighty-one others would follow.

It wasn’t always easy. The son of a music teacher, Dorsey was Irish, tough, something of a martinet. A few years earlier he had fought with his older brother, Jimmy, another fine musician, and broke up their band to go off on his own. Tommy built his own orchestra into a commercial and artistic success through a combination of will and musicianship. He built his sound around his own sweet trombone playing, as exemplified by his theme, “I’m Getting Sentimental Over You,” but also willingly turned the spotlight over to soloists and vocalists. He insisted on perfection from the band members and had no tolerance for the unkempt semi-bohemian styles that many musicians affected. He wanted his men to be clean-shaven and even held inspections before gigs. For the most part, the men responded; the members of the Dorsey band swaggered a bit, convinced of their superiority over other bands. But Dorsey, like Buddy Rich, was also a loner. That quality obviously touched Sinatra in ways that had nothing to do with music.

“Tommy was a very lonely man,” Sinatra told Douglas-Home. “He was a strict disciplinarian with the band — we’d get fined if we were late — yet he craved company after the shows and never really got it. The relationship between a leader and the sidemen, you see, was rather like a general and privates. We all knew he was lonely, but we couldn’t ask him to eat and drink with us because it looked too much like shining teacher’s apple.”

Sinatra remembered finally asking Dorsey to have dinner with him and another musician; Dorsey agreed and was touchingly grateful. “After that,” Sinatra said, “he was almost like a father to me.” Dorsey would, in fact, be godfather to Sinatra’s daughter Nancy. During these three years Sinatra absorbed many lessons from his surrogate father. One was about spacing a show, always meticulously planned by Dorsey. The Dorsey band wasn’t just playing music for dancers, it was also presenting a show, one that demanded its own structure, intelligent variations of up-tempo tunes and ballads, a sustained presentation that would leave the audience with a sense of completion.

Sinatra told me about Dorsey: “He put together a show like it was one long piece of music, or like an album — this was before the LP, and you couldn’t do records that way — with different moods and movements leading to a crescendo. He knew how to shift a mood so it didn’t all sound the same and bore the ass off the audience. It was dance music, first and foremost. But it was more than that. I always kept that in mind later, for my own shows and albums. Tommy didn’t spell it out to us, but he didn’t have to. It became part of you, just from doing it. Seven shows a day, sometimes, if you worked a theater. Three shows a night, if the gig was a dance somewhere. It became part of you.”

Dorsey’s own work on the trombone had a lasting influence on Sinatra’s style. There has been much discussion of the way Sinatra watched Dorsey’s tricks of breathing, in order to sustain long phrases. The writer and lyricist Gene Lees dismisses most of that as a myth. But in his essay on Sinatra in Singers and the Song II, Lees describes superbly what Dorsey’s real influence was on Sinatra the musician. He writes of Dorsey:

“He did … have remarkable breath control, and his slow deliberate release of air to support long lyrical melodic lines was indeed instructive to Sinatra and still worth any singer’s attention. Dorsey would use this control to tie the end of one phrase into the start of the next. Sinatra learned to do the same.”

Lees cites, as an example, their 1941 recording of “Without a Song.”

“Since Dorsey’s trombone solo precedes the vocal, the record provides an opportunity to observe how Sinatra was learning from Dorsey, and how far he had come from ‘All or Nothing at All.’ At the end of the bridge, Sinatra goes up to a mezzo-forte high note to crest the phrase ‘as long as a song is strung in my SOUL!’ But he does not breathe then, as most singers would. He drops easily to a soft ‘I’ll never know …’ This linking of phrases between the inner units, learned from Dorsey, gave Sinatra’s work a kind of seamlessness.”

To build up his breath, Sinatra spent long hours in swimming pools, often under water, and when not on the road used the outdoor track at a school in Jersey City. Dorsey’s long lines, his legato sound, his use of glissando movements, abruptly plunging deep into the lower register for certain effects — all marked Sinatra. But Sinatra could do things Dorsey could not do, for the simple reason that he was using the English language, with its creamy vowels and abrupt consonants. And he used it in a way that can only be described as urban. Again, Lees describes this very well:

“When you sing a long note, it is the vowel you sustain, almost always. Certain of the consonants, voiced or voiceless, cannot be sustained: b and its voiceless counterpart p, d and t, g and k. You cannot sing thattttt. It is impossible. You must sing thaaaaat or cuuuuup. Or taaaake. But certain other consonants, voiced and unvoiced — v and f, z and s — can be sustained, being fricatives, although I find the effect unattractive. You cannot sustain the semivowels w and y. But there are four semivowels that can be sustained: m, n, l, and r. Now, just as Spanish has long and short forms of the letter r — a double rr, as in perro, is rolled — correct Italian enunciation requires that you slightly sustain all double consonants. And Sinatra always recognized this principle, whether because of his Italian background or not. You hear it when he extends the l in Alllll or Nothing at Alllll.”

In addition, Sinatra’s delivery of certain words acquired a subtle New York flavor, Lees points out, because he “dentalized” ts and ds. That is, like many people from the New York area, he formed each consonant with the tongue against the teeth, rather than the gum above the teeth. In words like dream or tree, he could instantly pull it away, softening the following r. This made for a more fluid enunciation of many words and prevented the popping of consonants when using the microphone. This was never a problem for opera singers, or Broadway belters, but was essential when using a microphone in a recording studio, or the even clumsier microphones used on bandstands.

During this period Sinatra worked hard at mastering the microphone, knowing that it was his musical instrument. There were no portable mikes in those days; each microphone was attached to a stand. Almost all singers stood rigidly facing the mike and used their hands for dramatic emphasis. It was as if they were singing to the microphone, not the audience. Sinatra changed that, gripping the stand itself, and then, according to Lees, “moving the mike in accordance with what he was singing. And he was the man who developed this technique.” Movement was crucial to the performance. “Sinatra gripped the stand and drew the microphone toward him or tilted it away according to the force of the note he was putting out at any moment.”

Sinatra was then able to establish greater intimacy with the audience, shifting his attention from one young fan to another, but making each feel like the specific object of his attention. He never lost that ability to connect. It was at the heart of his intimate style. These factors combined to make the unique Sinatra sound: breath control and seamlessly sustaining notes; the subtlety of the New York speaking voice refined by impeccable diction; a natural, intimate style made possible by intelligent use of the microphone. Dorsey also established for Sinatra a standard of professional excellence that would endure for a lifetime.

Nobody can speak with absolute confidence about the artistic undertones of the Sinatra style. He spoke later in life about the effect of Billie Holiday on his work, citing her phrasing. I’ve listened to a number of tunes that were recorded by both, and I don’t hear that effect. But one night he said something about Lady Day that did make sense.

“What she did was take a song and make it hers,” Sinatra said. “She lived inside the song. It didn’t matter who wrote the words or the music. She made it hers. All the jerks who fucked her and left her. All the nights strung out on junk. All the crackers that treated her like a nigger. They were all in her music. That’s what she made out of those songs. She made them her story.”

At his best (and he sometimes made choices that were awful, or had them forced upon him) Sinatra did the same. He inhabited a song the way a great actor inhabits a role, often bringing his own life to the music. As a young singer, there wasn’t as much life to draw upon, but it did have a large share of hurts, some because he was Italian American, some because he felt he didn’t have enough formal education, others because of the way he grew up as an only child. Right from the beginning, he had a profound understanding of human loneliness. Some of this he must have also drawn from the silent presence of his father, the inconstant exuberance of his mother. Some of it must have been emphasized when he joined the company of the orchestras, living day and night with talented men who had lived other kinds of lives, rich with the presence of family.

“I’d be in the bus, and the guys’d be sleeping or drinking or talking,” he said once. “And I’d look out the window and see these houses with the lights on and wonder how they all lived. The houses looked warm. Safe. You know, normal. I was still a kid, but I knew that it was too late for me to have that kind of life.”

Riding those buses through America, Sinatra also must have known that he could never be a sideman, a part of a group, all for one, one for all. He wasn’t raised that way. He was raised to work solo.

ONE OF SINATRA’S most mysterious achievements was also the one that allowed him to endure for more than half a century after Harry James heard him in the Rustic Cabin. It was the nature of his audience. Sinatra started out with far more female than male fans. He ended up with more male fans. This happens to very few pop singers.

On the simplest level it was connected to the times themselves. For millions of women during the war, Sinatra was the romantic voice of the American homefront. He was singing to Rosie the Riveter, the symbolic woman who had walked into a war plant and found employment that was ordinarily reserved for men. She was more than a self-reliant patriot or an earner of a day’s pay for a day’s work. She was something new, and her newness began to transcend the work itself; Rosie the Riveter was soon asserting some of the prerogatives of men — smoking cigarettes, drinking when she wanted to drink, right up against the bar, sleeping around if she wanted to sleep around, or choosing her own erotic fantasies. The music of Frank Sinatra wasn’t used only by men to seduce women; during the conflict that Studs Terkel called “the good war,” some women used that music, with its expression of sheer need, to seduce the available men. Yes, Sinatra was singing to all those girls whose boyfriends were fighting in Anzio or Guadalcanal; some maintained a patriotic virginity; others went their own ways. At the same time, he was singing to those women, of whatever age, who had never managed to find a boyfriend at all and for whom Saturday night truly was the loneliest night of the week.

In his life Sinatra’s sudden, immense fame worked as a kind of aphrodisiac. There were then, as there would be during the long reign of rock and roll, groupies who would sleep with famous men to add them to scoreboards; the names were like the downed Messerschmitts or Zeroes painted by pilots on the sides of P-51s during the war. But there were also many less calculating females suddenly knocking on Frank Sinatra’s door. He certainly wasn’t so perfectly handsome that he seemed unattainable; he looked to some young women that he’d be as happy to meet them as they would be to meet him.

But the Sinatra fantasy was also safe because its consummation seemed so unlikely. The big reason was that he was also married, was living after June 1944 in Toluca Lake, California, with his wife, Nancy, his daughter, Nancy, and after September 28, 1944, his son. The boy was named Franklin (for President Roosevelt) Emanuel (for his agent, Manie Sachs) Sinatra. He wasn’t really a “junior” but would be cursed with the label of Frank Jr. for his entire life. In the wartime years Sinatra played by the rules of the publicity game; if that was what was required to become a gigantic star, then that was what he would do. And so he allowed fan magazines to photograph him with his family, first in Hasbrouck Heights, New Jersey (wearing a Crosby-style yacht cap, smoking a pipe, posing in the bar of his finished basement), and then in the grander circumstances of Los Angeles. His wife, Nancy, was always there, smiling in an amused way; in public she played the part of the older, wiser woman who was the guarantor of the innocence of the girls who wanted her husband.

This bow to the conventional pieties became part of the double image that Sinatra was conjuring: the traditionalist, with house and family, and the potential lover, consumed by loneliness and unrequited love. As a singer, he was almost always the lover. In American music of the time, Bing Crosby was the reigning husband.

He and Crosby met in 1943, liked each other, worked together on radio shows and patriotic rallies. But Crosby successfully presented a reassuring, almost paternal image to the audience, one whose wild oats had long ago been sown, and kept his personal life — and whatever private demons he might have had — safely behind his own walls. With Sinatra, public and private seemed to merge, and the result was a disturbing ambiguity. Yes, he had a wife and children and a house; but in the music he professed a corrosive emptiness, an almost grieving personal unhappiness. The risk attached to his kind of singing was that it promised authenticity of emotion instead of its blithe dismissal or the empty technique of the virtuoso. His singing demanded to be felt, not admired. It always revealed more than it concealed. Unlike the Crosby persona, Sinatra could not laugh off his losses. That transparency was essential to his music. But it didn’t make real life easier for him.

While Sinatra’s career was taking off after 1943, with hit records, radio shows, and movie contracts, rumors about his private life started finding their way into gossip columns. He was spotted with this starlet or that woman; on the road he seldom slept alone. Or so the rumors said. Some were certainly true. “You’re a young guy,” he said once, in another context. “You don’t say three Hail Marys and pray for sleep.” Sex, of course, was also about power. Young women could use sex to impose fleeting power over the famous young man; Sinatra, the new kid in town, could sleep with Hollywood movie stars to prove to himself that he had true power and would never end up back in Hoboken. But he also was learning that even after the most casual feasts, someone presents you with the bill.

Very early he came up against the terrible scrutiny that comes with fame — and he didn’t like it at all. It was one thing for an unknown Sinatra to live in Hoboken and have a fling in Englewood; nobody would ever know, except the principals. It was different for a star. Someone was always watching. Years later Sinatra was still struggling with the velvet prison of fame.

“It just changes everything,” he said. “You can’t go to a beach. You can’t walk into a movie. You can’t stand on a corner and eat a hot dog. You want the fame but, baby, you pay a price.”

During the war, rumors of Sinatra’s carousing didn’t matter to the young women in the audience. If Sinatra was indeed doing what he was accused of, the female audience wasn’t surprised. The subtext of his music suggested that he didn’t feel complete in his personal life; in a complicated way, these young fans also wanted the same chance that the other women seemed to be having. Most didn’t identify with Nancy; they envied her, even honored her, but they were more like the other women, desiring a night with Frank Sinatra with no illusions about living happily ever after. Everywhere on earth, wartime is a bad time for traditional values. When Sinatra did go home to Nancy, there were often angry confrontations, abrupt denials or dismissals, slammed doors. Sinatra didn’t handle any of this well. It was one thing to create romantic fantasies for strangers; it was quite another to deal directly with a humiliated wife. The emerging truth was quite unremarkable: like many other young men, Frank Sinatra was a good father and a poor husband.

In many ways he was a very lucky American. Timing is everything, in music and life. His career timing had been perfect. He was also lucky to have been declared 4-F. But his good fortune during the war hurt him when it was over. Absorbed with his expanding career, and perhaps fearful of his reception among the GIs, Sinatra didn’t make a USO tour until after the war in Europe ended on May 8, 1945. He was accompanied on the six-week tour by comedian Phil Silvers (with whom he had written “Nancy (with the Laughing Face)” as a birthday present for his daughter on her fourth birthday). On the long transatlantic journey to Europe, Sinatra was anxious. There had been predictions that the soldiers might be hostile, might throw eggs or tomatoes at the man who was making their girlfriends and sisters swoon while GIs were fighting the war. That didn’t happen. With shrewd advice from Silvers, Sinatra cast himself as a skinny underdog, an ordinary guy much like GI Joe. He made fun of himself and his image. He charmed the grizzled young veterans, expressed his gratitude to them, identified with them, and soon had them identifying with him. The press agents sighed in relief; so did Sinatra. Everything had gone smoothly. He’d even visited Italy and had met the Pope.

But when the veterans started coming home that fall, after the atom bombs ended the war with Japan, the smooth ride of Frank Sinatra started getting bumpier. The return of actors like Clark Gable and Jimmy Stewart reminded Americans that many show business figures had gone off to war. The ballplayers came home too, including Pee Wee Reese and Pete Reiser from the Brooklyn Dodgers, Hank Greenberg from the Detroit Tigers, Ted Williams from the Boston Red Sox, and, of course, the great DiMaggio. All were among the 9 million Americans who had served their country. More than half a million had been Italian Americans, thirteen of whom received the Congressional Medal of Honor while ten were awarded the Navy Cross. More than 300,000 Americans didn’t come home at all, including 13,712 from the state of New Jersey. And in every state in the Union, those who had been wounded and maimed tried to adjust to the changed country. Some have speculated about the effect military service might have had on Sinatra’s personality and career; that leads nowhere. For reasons that were honorable, he didn’t go to his generation’s war and had to settle for playing servicemen in eleven of his sixty movies. One thing is certain: for many of those who came back from World War II, the music of Frank Sinatra was no consolation for their losses. Some had lost friends. Some had lost wives and lovers. All had lost portions of their youth.

More important to the Sinatra career, the girls from the Paramount, and all their sisters around the country, started marrying the men who came home. Bobby socks vanished from many closets. The girls who once wore them had no need anymore for imaginary lovers; they had husbands. Nothing is more embarrassing to grownups than the passions of adolescence, and for many, Frank Sinatra was the teenage passion. Children were soon being born in unprecedented numbers, all those kids who a generation later would be known as the baby boomers. At the same time, the children of all those turn-of-the-century immigrants, now toughened by war, equipped with the benefits of the GI Bill, began leaving city ghettos for the expanding new suburbs; some became the first people in the histories of their families to go to universities.

Swing music was rapidly dying, for complicated reasons. Most important was a two-year strike by the American Federation of Musicians, which, among other things, forced Sinatra to make his first sides for Columbia Records singing a cappella with a choral group. The strike kept the big bands out of the studios, unable to reach the mass audience with new material. Goodman, Dorsey, and others sounded stale; Glenn Miller was dead, having disappeared over the English Channel. The economics of the bands also changed. Postwar inflation drove up the cost of transportation. Sidemen who gladly worked for $40 a week during the Depression were now asking for $200, with soloists demanding more. Musically, the big band sound was exhausted. From Fifty-second Street to Minton’s Playhouse in Harlem, the hippest fans were now listening to bebop, to Charlie Parker and Dizzy Gillespie, Fats Navarro, Max Roach, and others — all of them playing in small groups that were formed during the musicians’ strike. Jazz had become a freer, more democratic form of chamber music, an ongoing jam session liberated from the dictates of rigid big band arrangements. Younger fans, with only vague memories of the Depression, were listening to mush or to novelty tunes. For many other people, the music of the swing bands reminded them of the war, a time they wanted to forget. It would be a long time before nostalgia would work its magic, transforming that music into a symbol of a more innocent America.

Musically, Sinatra reacted to the postwar climate in several ways. Even before leaving for his USO tour, he had experimented with other sounds, recording four sides with a black gospel-style group called the Charioteers and two others in a rumba rhythm with the orchestra of Xavier Cugat. He conducted an instrumental album of Alec Wilder songs. He wrote the lyrics to an aching ballad called “This Love of Mine.” But basically, he stayed with variations on his own traditional taste in ballads and jump tunes, most of them arranged by Stordahl. Many were very well done, enriched by strings and woodwinds, but the mysterious currents of public taste were shifting. The fans were groping for something new, sounds that would express the exuberance, optimism, and, in certain ways, mindlessness of the years after the war. Some would find it in singers as varied as Billy Eckstine, Frankie Laine, and Guy Mitchell. Perry Como had a string of hits. Doris Day became a star, along with Peggy Lee, Vaughn Monroe, Vic Damone, and the Four Aces. Even Gene Autry had a hit in 1949 with “Rudolph the Red Nosed Reindeer.” There were no signs of panic in Frank Sinatra, but he must have been uneasy.

He put much of his energy into the movies. In 1945 he won a special Academy Award for a ten-minute short called The House I Live In. He played himself, leaving a radio studio and running into some kids who are beating up another “because we don’t like his religion.” Sinatra tries to straighten them out and sings the title song. At the time, Sinatra’s liberal politics were widely known. Most performers of that era kept their politics to themselves; let Democrats in the audience believe they were Democrats, Republicans think they were Republicans. But Sinatra was a new breed in Hollywood. He publicly supported Franklin D. Roosevelt and visited him in the White House. This was more than familial loyalty to his mother, Dolly; Sinatra was one of the first big stars to use his fame to promote his politics, and those politics were, by all accounts, deeply felt. He made an effort to visit schools and talk to teenagers about bigotry, always citing the hurtful words that had been hurled at him as a boy in Hoboken. He signed petitions. He sent money to candidates. The short, directed by Mervyn LeRoy from a script by Albert Maltz (later to become one of the Hollywood Ten during the anticommunist crusade), impressed the critics.

“Mr. Sinatra takes his popularity seriously,” said the reviewer for Cue. “More, he attempts to do something constructive with it. Millions, young and old, who will not or cannot read between the lines of their daily newspapers and are blind to the weed-like growth of bigotry and intolerance planted by hate-ridden fanatics, will listen carefully to what Mr. Sinatra has to say in this short film.”

He followed the short with Anchors Aweigh (1945), a bright, good-natured musical about sailors on shore leave. Sinatra was superb. He worked with Gene Kelly — worked very hard indeed, and his dance number with Kelly shows it; the routine is full of high spirits, self-kidding, and good dancing. “I never worked so goddamned hard in my life,” he said later, laughing in a fond way. “Kelly was a brute.” But those were the days of the major studios; at MGM, where Sinatra had a five-year contract, he often couldn’t choose his vehicles. The films that followed were mediocre (It Happened in Brooklyn, RKO’s The Miracle of the Bells), and one, The Kissing Bandit (1948), was dreadful. Set in the nineteenth century, this semimusical stars Sinatra as a young Mexican fresh out of an Eastern college who goes back to Old California to run the family rancho. He even sings one song while riding a white horse. Sinatra’s love interest is Kathryn Grayson, and the movie also features J. Carrol Naish, the Irish actor from Life with Luigi, who plays Sinatra’s Mexican foreman, Chico. “I hated reading the script,” Sinatra later said, “hated doing it, and, most of all, hated seeing it. So did everyone else.”

He wasn’t truly good again as a movie actor until 1949, when he teamed up once more with Kelly in an MGM musical called Take Me Out to the Ball Game, and quickly followed it with a movie masterpiece, On the Town. Another story of sailors on shore leave, this time in New York, the film was codirected by Kelly (who also stars) and Stanley Donen. It was written by Betty Comden and Adolph Green. Music for a ballet was composed by Leonard Bernstein. The reviews were raves. Sinatra’s star should have been ascending.

Instead, he was heading for the Fall.

AFTER THE FALL, the Comeback.

For two long and terrible years, Sinatra was a mess. He continued working, making records, appearing on television, performing in small clubs. But in 1952 and 1953 he had no records at all on the Billboard singles charts; he had made those lists every previous year since 1940. His three-year television contract with CBS was canceled after thirteen weeks because he wouldn’t take the time to rehearse and was abusive to too many people. A 1952 movie called Meet Danny Wilson contained many semi-autobiographical touches, including a racketeer who takes 50 percent of the earnings of a singer played by Sinatra. The movie has many fine songs, including “All of Me,” “I’ve Got a Crush on You,” “That Old Black Magic,” and “She’s Funny That Way.” But it was poorly directed and shabbily produced. Sinatra did a live engagement to help the movie when it opened at the Paramount in New York in 1952. That year I was sixteen, and I went to see him, for the first time, in the theater that only eight years earlier was loud with hysterical adoration. He was as good as everybody said he was: in command, singing with energy and feeling. But the theater was half empty. In other parts of the United States the movie opened and closed. That seemed to be the end of Frank Sinatra’s Hollywood career.

Sinatra was drinking hard and smoking too much, and then drinking again. Failure stoked the fires of his rage and increased his need for alcohol; both increased his sense of personal dissolution. His artistic energies were also being exhausted by the fierce entanglement with Ava Gardner. Any love affair is a creative act, part imagination, part practice; often, it can lift an artist to new levels of exalted energy. But a doomed and tumultuous love affair, on the model of the Sinatra and Gardner coupling, can destroy creativity. For months their affair and marriage seemed to obliterate the basic optimism required by the romantic impulse, so essential to Sinatra’s art. The vision of earthly happiness, that elusive goal that calls forth so much lyricism, was being maimed by a corrosive cynicism.

While Sinatra’s career declined, Ava’s star shone more brightly. He began to resemble an adjunct to her career, following her to movie locations in Spain, England, Africa, and Mexico. They drank hard. They quarreled. They reconciled. Sometimes Sinatra did his drinking in the empty time when she was away making movies and he was trying to make an impact on television. But distance didn’t help him regain clarity or a sense of perspective. Instead, jealousy ate at his guts. In Clarke’s or Toots Shor’s in New York, in the haunts of a fading Hollywood, or in his own apartment (since he and Ava never did establish a home), he seemed to bounce off the walls, like a drunk who had stayed too long at a party.

But then, slowly, there was a shift. He tried, and failed, to get the part of Johnny Romano in the film of Willard Motley’s Knock on Any Door; the role went to young John Derek, whose impossibly perfect looks resembled an illustration from Cosmopolitan magazine. Sinatra, at thirty-four, was too old, but Johnny Romano’s motto was one that Sinatra might have felt deeply: “Live fast, die young, and have a good-looking corpse.”

After he was dropped by MCA, Sinatra moved to the William Morris agency and began focusing his attention on a novel by James Jones called From Here to Eternity. The book was a huge bestseller, a densely detailed story about soldiers based in Schofield Barracks in Pearl Harbor on the eve of the Japanese attack. All the characters, in one form or another, had been shaped by Prohibition and the Depression, but Sinatra focused on the role of a tough little Italian American named Angelo Maggio. “I knew Maggio,” Sinatra said. “I grew up with him in Hoboken.” Unlike Meet Danny Wilson, this was to be a major film, with a healthy budget; it would have what Sinatra liked to call “class.” It was to be made by Columbia Pictures, whose boss was the tough, vulgar Harry Cohn. The director was to be Fred Zinnemann. His High Noon the year before was a parable about McCarthyism that simultaneously breathed new life into the western and into the career of Gary Cooper, who won an Academy Award as best actor. Sinatra began to plead for a chance to play Maggio.

He had a little help from his friends. There is neither proof nor logic to Mario Puzo’s fictional version in The Godfather, where the Mob cuts off the head of a racehorse owned by the studio boss and deposits it in his bed, thus persuading the studio to give the part to a character based loosely on Sinatra. To be sure, Cohn knew Longie Zwillman, who had an affair with Columbia star Jean Harlow in the 1930s, and probably took loans from Zwillman in the lean days of the Depression. But Maggio was a minor part in a movie starring Burt Lancaster, Montgomery Clift, and Deborah Kerr. If the Mob had occult powers, why not get him the starring role? The myth endures. As Mario Puzo himself once said, fiction is the art of “retrospective falsification.”

The facts were more banal. Sinatra’s new agents were working hard behind the scenes. Sinatra himself pleaded with producer Buddy Adler for a chance to do a screen test. He also called Adler’s boss, Harry Cohn, who owed him a favor. More important, Ava interceded with Cohn’s wife, Joan, who put in a good word with her husband. Ava also met with Cohn himself, offering to make a movie at Columbia for nothing, if only he’d give Sinatra the part of Maggio. The studio moved cautiously, primarily because the success of High Noon had given director Zinnemann some power; they could suggest Sinatra but couldn’t order him into the movie. Most of the key players at the studio, including Zinnemann, believed that Sinatra was primarily a singer, not an actor, and would add nothing to the movie’s box-office appeal. Everybody in Hollywood knew that Sinatra was a troubled man, increasingly viewed by the public as Mr. Ava Gardner. It would be better to just get a good actor. A fine, but then unknown, New York actor named Eli Wallach was the favorite.

In November 1952 Sinatra was in Kenya with Ava as she worked with Clark Gable and Grace Kelly in John Ford’s Mogambo. At this point, he seemed to have given up any realistic hope of getting the part. Then, suddenly, the call came from Columbia, asking him to fly home for a screen test. Sinatra was elated. So was Ava. Sinatra took the next plane out. Without Frank’s knowledge, Ava flew to London for her second abortion of the year.

Sinatra’s screen test was splendid. When it was over, Zinnemann called Adler and said, “You’d better come down here. You’ll see something unbelievable.” At the same time, Sinatra’s luck began to return. The men who made such decisions agreed that Wallach’s screen test was even better than Sinatra’s. But then Wallach got the opportunity to work with director Elia Kazan on Camino Real, the new play by Tennessee Williams. Kazan and Williams were at the peak of their artistic success; Wallach chose the theater over the movies. And Sinatra agreed to play Maggio for a mere $8,000. Shooting would begin in March of 1953. Nobody yet knew it, not even Sinatra, but the Comeback had begun.

OVER THE YEARS I’ve learned much about Frank Sinatra and his music from a number of people, ranging from my old neighborhood friend, Bill Powers, to the great producer, Jerry Wexler. Nelson Riddle, while making his albums with Linda Ronstadt in the 1980s, also gave me insights into the man and his work. But across the years much of my instruction has come from Jonathan Schwartz. He is a fine writer, a musician, and a disc jockey at WQEW in New York. Sinatra once said of him: “He knows more about me than I do.” Jonathan was generous in reading an early draft of this book and I am, again, in his debt. He is not, of course, responsible for errors that might have eluded both of us nor for my interpretations of the man and his music.

The Sinatra music has been scrambled and repackaged by various companies into a confusing mess. This was compounded by Sinatra himself, who for reasons of contractual argument, artistic dissatisfaction, or sheer laziness repeatedly went back to certain songs. But these albums are my own favorites: In the Wee Small Hours, Songs for Swingin’ Lovers, Only the Lonely, Come Fly with Me, A Swingin’ Affair, Songs for Young Lovers, Come Dance with Me, Francis Albert Sinatra & Antonio Carlos Jobim, September of My Years, Sinatra at the Sands (in spite of the wretched monologue), Nice ’n’ Easy, and Swing Along with Me. There are a variety of boxed sets of his work at Columbia and earlier music with Tommy Dorsey and Harry James. All are rewarding, even the dumb novelties of the moment. I like the two-CD set from Columbia called Portrait of Sinatra and the five-CD package from RCA Victor called The Song Is You, which contains virtually all the Tommy Dorsey recordings. It is particularly interesting as a means of tracing the musical lessons learned by Sinatra from Dorsey. Needless to say, reactions to anyone’s music are always subjective, but for me, the above albums offer many pleasures.

“Hugely readable. … Hamill’s long history as a New York journalist, his knowledgeable love for the city, and his writerly exuberance explode here into a New York fantasy. … Forever is old-fashioned storytelling at a gallop.”

— Washington Post Book World

Pete Hamill is a novelist, journalist, editor, and screenwriter. Among his bestselling books are the novels Forever and Snow in August and the memoir A Drinking Life. He writes a column for the New York Daily News.