Why Sinatra Matters


By Pete Hamill

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In honor of Sinatra’s 100th birthday, Pete Hamill’s classic tribute returns with a new introduction by the author.

In this unique homage to an American icon, journalist and award-winning author Pete Hamill evokes the essence of Sinatra–examining his art and his legend from the inside, as only a friend of many years could do. Shaped by Prohibition, the Depression, and war, Francis Albert Sinatra became the troubadour of urban loneliness. With his songs, he enabled millions of others to tell their own stories, providing an entire generation with a sense of tradition and pride belonging distinctly to them.

With a new look and a new introduction by Hamill, this is a rich and touching portrait that lingers like a beautiful song.


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IN THE LATE SPRING OF 2015, Francis Albert Sinatra was suddenly alive in the chilly New York air.

He had died in 1998, aged eighty-two, and for a long time seemed to have become a permanent part of a vanished century. But in 2015, there was Sinatra, the subject of a superb four-hour documentary on HBO. There was Sinatra's voice on radio stations all over the country, as vigorous and subtle as it was in his prime when he became a major part of the soundtrack of several generations. There was Sinatra in newspapers and magazines, an object of nostalgic admiration, affection, loss, and sometimes critical judgment. The reason for all this attention? If Sinatra had lived on, he would be one hundred years old on December 12.

A friend called one morning to say that there was a splendid gallery show at the Library for the Performing Arts in Lincoln Center celebrating the centenary of Sinatra's birth. Three mornings later, with a few friends, I wandered by for a look at Sinatra: An American Icon. The show was dazzling. Sinatra was alive again in a time of Prohibition lawlessness, when the Mob was creating itself from California to Hoboken. Then through the economic pain of the Depression and the fierce sense of loss during World War II, in the social banality of peacetime and the paranoia of McCarthyism. In his music, Sinatra expressed those times, turning separation that could never be healed into high popular art. Almost always, in the beginning, he was singing to, and for, the girls who were left behind.

The Lincoln Center show was also pervaded by Sinatra's lifetime struggle against loneliness. He was an only child, growing up surrounded by large families jammed into tenements. As an apprentice troubadour, he passed through strange towns and cities where it was always two o'clock in the morning. Sometimes he found company and warmth, even love. Many nights he slept alone.

Hating self-pity, the vulnerable young Sinatra was learning how to be stoic. Later, in his maturity, he used irony and laughter to protect himself, even when talking about the man he saw in the mirror. As with millions of American men, his isolation was often caused by the four-letter word called love. The emotions of the situation are perhaps best expressed in his version of "It Never Entered My Mind" (Rodgers and Hart, 1940), full of shame, foolishness, regret. In other songs too. But as the world moved on, Sinatra also came to understand that isolation, privacy, solitude, were not always the same as loneliness.

I knew Sinatra only for a few years in the 1970s (as this book briefly relates), always seeing him in New York. But in the Lincoln Center gallery I also got to see Sinatra as a chubby infant, as a young kid, as a teenager who was a bit of a dandy (a part financed by his saloonkeeper mother, Dolly, who was also a Democratic Party ward heeler). Other visitors to the gallery seemed as fascinated as I was. We were all squinting at what was before us, and seeing into the invisible distant past. Sinatra's past. Our own disjointed fragments of the past.

Sinatra the public man was, of course, well documented. There he was, smiling or somber outside theaters or openings, or if we were lucky, if we could afford the price of admission, in small clubs in big cities. But there were no pictures of him alone on the Hoboken waterfront, staring across the Hudson at the magical New York skyline. No notes on what he was thinking.

Years later, we would see those old black-and-white newsreels from his early days as a star, the young man from Hoboken now labeled The Voice, 4-F during the war, inspiring forlorn bobby-soxers to various levels of teenage ecstasy at the Paramount Theatre.

From the packed balcony to the jammed sidewalk in front of the theater, this was a brief time when every night in Times Square seemed like New Year's Eve. Sinatra was singing with Harry James or Tommy Dorsey or Benny Goodman. Many of the young women in the dark, distant seats surely ached for their own young men, off fighting a war in the Pacific or North Africa, Anzio or Normandy. A lot of the young women just as surely had to fight the desire to mother the skinny kid up there on stage. But, hey, he was married, to Nancy Barbato, with the laughing face. The Sinatras even had a couple of kids, young Nancy and Frank Jr., each born in Jersey City. And when at last World War II ended and the survivors slowly came home at last, their third child, Tina, was born in 1948. In California.

But there were other Sinatras on display now at Lincoln Center. One was the movie actor. A visitor could stand and watch The House I Live In, a ten-minute short made in Hollywood in 1945. The film won a special Academy Award in 1946. The screenplay was written by Albert Maltz, the music by Earl Robinson—who was later blacklisted in Hollywood. The action took place in an alley behind a theater. A group of teenage white kids was hanging out when Sinatra came out for a smoke. The apprentice hoodlums started bullying a Jewish kid, who escaped. And Sinatra started talking to the bullies. Upset. Angry. Urging upon them a sense of decency and respect for kids who were not like them. We're all Americans, Sinatra tells the kids. (This was when the full horrors of what soon became known as the Holocaust were not yet known.) On the soundtrack, Sinatra sang the title song, by Abel Meeropol and Earl Robinson, which became a national hit. For years he continued to sing it, defying blacklisters and anticommunist crusaders. Later, after leaving the Democrats, he even sang it for Ronald Reagan.

Beyond another glass wall, there was a pair of white shoes. A small monument to Sinatra's talents as a dancer. One white shoe is signed by Sinatra. The other shoe by Gene Kelly. The two men kept each unmatched pair as a souvenir from the making of the 1945 film Anchors Aweigh. In the film, Sinatra is very good, in an unforced way.

And wait: a few yards down, there were some paintings most of us had never seen before, even in print. Paintings by Frank Sinatra. They are very well executed, abstractions that seem like expressions of painted music. No clowns with grotesque mouths. No gorgeous women posed like fleshy trophies. Sinatra's paintings are spare triumphs of solitude.

Other displays were full of objects, the nitty-gritty of Sinatra's life: early contracts, cameras, New York Yankees jackets, a number of driver's licenses, an Oscar statuette, slippers and pajamas, album covers, posters, snapshots, letters. Each had some private meaning that caused Sinatra to save them. Almost surely, the meaning was connected to love. And binding together all of the exhibition material, playing on speakers, was that voice, thin, even tentative when young, maturing into a man's rich—and knowing—baritone as he grew older.

He drew his material from what is now known as the Great American Songbook, the words and music of the Gershwins, Harold Arlen, Johnny Mercer, Leonard Bernstein, Stephen Sondheim, Hoagy Carmichael, Arthur Schwartz, and others brought to fresh vivid life in many instances by the great Nelson Riddle's arrangements. The writers and composers were almost all from cities and thus perfectly complemented Sinatra's urban style. Together, they were makers of the American popular classics. All were driven by the music.

There was more to the Sinatra story than a smooth road to success. As noted in this book (and others), after the war he lost much of his teenage audience. Some of the returning GIs despised him for ducking the war (although his deferment was legitimate). Some years later, those same veterans became Sinatra fans thanks to the power of his art. But there were personal bad times too. His marriage to Nancy began to disintegrate. He fell in mad, passionate love with the star Ava Gardner. After his divorce, he married her. And started drinking too much. There were several suicide attempts, perhaps intended to impress Ava. He had fights with intrusive gossip columnists. He lost his record contract and, for a while, his voice. He was no longer welcome in Hollywood. Sinatra had knocked himself flat.

And then he got up.

The Comeback started in 1953 with his performance as Maggio in From Here to Eternity, based on the fine James Jones novel. His performance became part of the Sinatra legend, and he won an Academy Award for best supporting actor. He began to get offers of starring roles again. And made television appearances. And sold records. A lot of them. Around the same time, the gossip brigades began linking him with the Mob. For thirty years he would be investigated by law-enforcement agencies. They never found evidence for a single indictment. In that world, he was a victim of stereotyping; the facts didn't matter. He was Italian, right? Wrong. He was American.

He also began to live a different part of the legend: the great lover. The better-known female players were Bacall, Prowse, Monroe, Dickinson, and a few others. All were consenting adults. He also sought the company of his male friends, who made up the Rat Pack: Dean Martin, Sammy Davis Jr., Joey Bishop, Peter Lawford. They would often travel to Las Vegas, Miami, New York. Sometimes they could be funny. Most of the time they seemed to be merely performing.

There remain many mysteries about Sinatra. But this I truly know. My life would not have been the same without his music. Writing these words, and many others, I heard Sinatra singing "In the Wee Small Hours of the Morning" and "I've Got the World on a String." I want to hear "How Deep Is the Ocean" and "Fools Rush In" and "Someone to Watch Over Me." I'm in a hotel in Barcelona and from the next room I hear Cole Porter's "You'd Be So Nice to Come Home To." Later, I hear "Night and Day." And "I'll Be Around" and "Ill Wind."

When the music stops, I can kiss my wife and hug her. I can walk with her in the cold streets. I can remember what it was like to be twenty-two. With any luck at all, I can dance.

—Pete Hamill, June 1, 2015


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.

He was wonderful with children, including my two daughters. He was funny. He was vulnerable. I never saw the snarling bully of the legend. That Frank Sinatra certainly existed; on the day that his death made all those front pages, there were too many people who remembered only his cruelties. But he never showed that side of himself when I was around. On those nights, I was in the company of an intelligent man, a reader of books, a lover of painting and classical music and sports, gallant with women, graceful with men. Perhaps he was just donning a mask in my company, presenting images to a writer so that they would be remembered by the writer in a certain way: a kind of performance. Or perhaps the snarling bully was the true masked character, a clumsy personal invention, and behind the mask there was simply a young man afraid of the world. Or perhaps, by the time I knew him, he had just grown out of his angers, exhausted them, and settled for what he was and the way he was regarded. I don't know. Like all great artists, Frank Sinatra contained secret places, abiding personal mysteries, endless contradictions. On occasion, a curtain would part, there would be a moment of epiphany, and I could see the uncertain older man who wanted to understand what it all meant, the man who said that dying was a pain in the ass. I liked that man very much.

This book does not pretend to be the final word on Frank Sinatra. Several full-scale biographies have already been written, each with its attendant excellencies; more are sure to follow. But there were aspects of this man that should be remembered and honored. In Sinatra's time, his fame as a singer spread from his own country to the world. His turbulent personality, often shadowed by notoriety, seemed inseparable from the style and originality of his art and gave him an essential place on the public stage of the American century. Now Sinatra is gone, taking with him all his anger, cruelty, generosity, and personal style. The music remains. In times to come, that music will continue to matter, whatever happens to our evolving popular culture. The world of my grandchildren will not listen to Sinatra in the way four generations of Americans have listened to him. But high art always survives. Long after his death, Charlie Parker still plays his version of the urban blues. Billie Holiday still whispers her anguish. Mozart still erupts in joy. Every day, in cities and towns all over the planet, someone discovers them for the first time and finds in their art that mysterious quality that makes the listener more human. In their work all great artists help transcend the solitude of individuals; they relieve the ache of loneliness; they supply a partial response to the urging of writer E. M. Forster: "Only connect." In their ultimate triumph over the banality of death, such artists continue to matter. So will Frank Sinatra.






  • "The most intimate and thoughtful eulogy for 'the Voice'....It leaves you wanting to listen again to Sinatra's best songs."—Entertainment Weekly
  • "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

On Sale
Oct 20, 2015
Page Count
208 pages

Pete Hamill

About the Author

Pete Hamill (1935-2020) was a novelist, journalist, editor, and screenwriter. He was the author of twenty-two books, including the bestselling novels Tabloid City, North River, Forever, and Snow in August, and the bestselling memoir A Drinking Life

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