Why Sinatra Matters

1 IN THE WEE SMALL HOURS

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.

II. That night came back to me, along with a dozen others, when I heard that Frank Sinatra was dead at eighty-two. I was in the Miami airport, catching an early flight back to New York, after sitting on a panel about the future of newspapers. I had checked in and picked up my boarding pass. Then I saw about a dozen people staring up at a monitor. CNN. The announcer looking grave. I couldn’t hear the sound. But then there were some clips and the legend “Frank Sinatra 1915–1998.” And I was like all the others in that sterile morning place, sliding into the blurred places of memory.

There was a radio on the window ledge in the kitchen of the tenement in Brooklyn. Through that window, past the radio, out across the backyards, we could see the skyline of New York to the right and the Statue of Liberty in the harbor and the low ridge of Staten Island and the gray smudge of New Jersey beyond. The harbor was thick with ships, heading off through the Narrows to the war. Sometimes the sky was dark with B-17s. At night the skyline vanished into blackness, the lights turned off, as were so many other things, for the duration. There was no television then, and so the radio served us kids as narration and sound track. From that little Philco, we heard about the invasion of North Africa and the assault on Sicily and the fighting at Anzio. The story of the war was all mixed up with the crooning of Bing Crosby and the score from Oklahoma! and the Andrews Sisters and Glenn Miller and, at some point, Frank Sinatra.

On days of snow or rain, when we could not go down the three flights to the street, those words drifted through the railroad flat. They seemed thin, even trembling, unlike the confident baritone of Crosby, but there was a kind of defiance in them too. I was six when the war started in 1941, and my brother Tommy was two years younger; we were too innocent to connect Sinatra’s words to a longing for women. They seemed to be about unconditional surrender, as declared by Franklin D. Roosevelt, whose picture was up on the kitchen wall. It was as if Sinatra were saying the words to Hitler and Tojo. We’re coming to get you. And it’s all or nothing at all.

In the neighborhood we began to hear arguments among the kids just older than us. Crosby versus Sinatra arguments. They had nothing to do with the words. And it was not simply another division between the Italian American kids and the Irish American kids. Some of the Irish guys were Sinatra fans; some of the Italians went for Crosby. It was about his sound. And sometimes about other things.

There were always newspapers in our flat. The News and the Mirror, the Journal-American and the Brooklyn Eagle. And they began printing stories about Sinatra. The Voice. Swoonatra. Hysterical girls roaring at the Paramount, over in Manhattan, which we called New York. In June 1944 the Allies invaded France, heading for Berlin, and the lights went on again in the mighty skyline. For weeks after D-Day I would go up to the roof alone and stare at the skyline, glittering and impossibly beautiful, like the towers of Oz. And from the open windows of the tenements I could hear the battle between Crosby and Sinatra.

I was too young to choose sides. But my father was definitely a Crosby man. He was a good singer and could deliver pretty fair Crosby renditions at christenings or wakes or from his spot at the bar of Rattigan’s. In dinner-table discussion my mother was also a fan of Crosby. But in the Brooklyn mornings she always listened to Martin Block on WNEW, and that meant she also listened to Frank Sinatra. She would sing along with him in her light soprano voice, not judging the music but embracing it. Still, among the immigrants in the neighborhood, Crosby was generally triumphant. He was all over the radio. The few people who owned phonographs played him all the time. (We did not own one.) The jukebox in Rattigan’s Bar, across the street, was fat with Crosby 78s, and in the summer you could hear him singing through the open doors. He was sunny. He was optimistic. He was casual. He said we had to accentuate the positive, ee-liminate the negative, and not mess with mister in-between. He said that if we didn’t give a feather or a fig, we could grow up to be a pig.

In addition, Crosby had played a priest in Going My Way. A Catholic priest, for God’s sake, whose best friend was an Irishman from Ireland, an older priest played by Barry Fitzgerald. In the movie, which the whole neighborhood went to see during the summer of 1944, Father Crosby saved Father Fitzgerald’s run-down parish, St. Dominic’s, by writing songs, and the church was in a neighborhood that looked very much like ours. Ordinarily, that would have been enough for my father, who was an immigrant from Ireland, as was my mother. But there was still another factor.

Our small part of America was seeing many things through the prism of the war. We lived in a working-class neighborhood of Irish, Italian, and Jewish Americans; most of its young men were off at the war. It was the kind of neighborhood that provided troops for the infantry, and in many windows, as the war ground on, there were small flags bearing gold stars, indicating that one of the young soldiers would be young forever. My father didn’t go to the war. He had lost his left leg while playing soccer in the immigrant leagues in 1927; the bones were smashed, gangrene set in overnight, penicillin did not yet exist, and they amputated in the morning. Crosby didn’t go because he was too old, but in the judgment of the neighborhood, he did the next best thing: he made many trips for the USO, entertaining troops in the company of comedians and beautiful women. But Sinatra was a separate case; he was the right age and he had two arms and two legs. Why couldn’t he do what stars such as Clark Gable, Glenn Miller, or Jimmy Stewart were doing, and insist on being taken by one of the armed forces? Why couldn’t he at least make a USO tour?

The male anger against Sinatra came to a head in October 1944, when he played the Paramount again and 30,000 mostly female fans erupted into a small riot outside the theater. When a male dissenter in the Paramount balcony fired a tomato at the stage, he had to be rescued from women who were trying to beat him to death. Breathless accounts of these events were all over the newspapers and the radio. At the same time, the first V-2 rockets were falling on London and American troops were fighting their way into Germany, taking heavy casualties. In our neighborhood, where the war was not a distant abstraction, the phenomenon of young Frank Sinatra was discussed with much heat in the bars and on the street corners and in the kitchens.

I don’t get it, my father would say. All those girls going nuts for a draft dodger.

He’s not a draft dodger, my mother would say. He’s 4-F. He’s got a punctured eardrum. He tried to join three times, and they turned him down. It was in the papers.

The papers, he sneered. You believe the papers?

Flying north from Florida, I could remember all that argument and my own youthful wonder about its passion. At nine, I was too young to understand what Sinatra was doing with his music. I did know it was different. Crosby made us feel comfortable and, in some larger way, American. But there was a tension in Sinatra, an anxiety that we were too young to name but old enough to feel. During the last six months of the European war, when men were dying by the thousands in the Battle of the Bulge, it was confusing to hear songs that contained so much anguish. Or loss. Or loneliness. I would see young women pushing strollers along the avenue, their men off at war, see them pausing to look at the front pages on the newsstands, see the way their faces clenched, and I wished that Bing Crosby could sing to them and make them feel better. It took me a long while to understand that it was Frank Sinatra who was giving words and voice to the emotions of their own roiled hearts.

III. Years later, when I was a reporter and then a columnist for Dorothy Schiff’s New York Post, I got to know Sinatra. Cannon introduced me to him after the Floyd Patterson — Sonny Liston fight in Las Vegas in 1963. We were together on other evenings. On the surface, this seemed strange, another contradiction in the character of a man dense with contradictions. Sinatra had wasted too much of his adult life in vicious quarrels with newspapermen and gossip columnists, had punched out at least one columnist (the awful Lee Mortimer), and was continually in rumbles with paparazzi.

“Sinatra’s idea of paradise is a place where there are plenty of women and no newspapermen,” said Humphrey Bogart, who was sixteen years older than the singer and a kind of hero to the younger man. “He doesn’t know it, but he’d be better off if it were the other way around.”

Perhaps, as he moved toward sixty, Sinatra came to understand what Bogart meant. Certainly, when he was in New York, he sought out his favorite newspapermen. Cannon was his friend, while the rest of us were friendly acquaintances. Cannon was only five years older than Sinatra, a New Yorker shaped by Prohibition and the Depression, the myth of 1930s Broadway, and World War II in Europe, where he served as a correspondent for Stars and Stripes. They spoke the same language, shared passions for boxers, ballplayers, and beautiful women. Cannon brought a poetic language to his sports columns, some of which were shaped like songs, and his essentially romantic vision of that world was saved from sentimentality by a knowing New York tone. Like Sinatra, he was afflicted by insomnia and bouts of personal loneliness; he read widely and intelligently, deep into the night. Sinatra never gave up the whiskey, but he was a reader too; he and Cannon talked at all hours of the night about books, and it was Cannon who urged him to read Nelson Algren’s The Man with the Golden Arm, which was the basis of one of Sinatra’s finest movies. It didn’t matter where they were staying; insomniacs without wives can always be reached by phone.

Cannon also got Sinatra to read Murray Kempton, who was writing his brilliant column for the New York Post in the same years that Cannon was the star of the sports section. Kempton was an absolute original who brought a unique, mandarin style to newspapers; on some days it was as if Henry James had agreed to cover the longshoremen’s union. He had an extraordinary sympathy for rascals, outcasts, those subjected to lofty moralizing. Nobody ever wrote more intelligently about Sinatra than Kempton did in a handful of columns across the years. But Kempton, who also liked his whiskey, was not a man who moved easily through the night. It was hard to imagine him sitting around in saloons. But Sinatra loved his work and would have his columns (and Cannon’s) airmailed to him each day in California. “The man is a marvel,” he said to me once about Kempton. “It’s like listening to Louis Armstrong, or Roy Eldridge: you don’t know where the hell he is going, but somehow he gets there and it knocks your socks off.” He made certain that Kempton covered the 1961 inaugural party for John F. Kennedy, which Sinatra produced. He joined him occasionally at more formal parties in New York, sometimes at his own apartment on East Seventy-second Street, near Third Avenue. He sent him fan mail, which he signed “Francis Albert.” But he didn’t call much on the telephone. “Kempton is one of those guys,” he explained, “that makes me feel tongue-tied.”

I was twenty years younger than Sinatra, but he seemed to be comfortable when I was around. It certainly helped that Cannon and Shirley MacLaine had vouched for me, and he was impressed that I knew Kempton. There might have been one other factor: Cannon and I were both high school dropouts, as was Sinatra. (Oddly, Cannon and I had dropped out of the same institution, a great Jesuit high school called Regis.) This might have meant more to Sinatra than it did to us; in a very important way he defined success as a triumph over the odds.

“Every time they print your column,” he said to me once, “you are getting your fucking diploma.”

I laughed. But he was serious.

Later, Sinatra had one other newspaper friend, Sidney Zion, now a fine columnist for the New York Daily News. Zion came out of Paterson, New Jersey, went to law school, worked as a prosecutor, and then became a reporter for the New York Post. Like all of us at the paper, he worshiped Kempton. But he had been shaped by the traditions and lore of urban New Jersey. The figure of Frank Sinatra was an immense part of that tradition. Zion loved the music that Sinatra loved most, the music of the hours after midnight. He loved saloons. He loved smoking and drinking (and still does). He is a wonderful storyteller.

“I got to know him around 1980, the time of the Trilogy album,” Zion told me. “I did a piece about the old music for the Times, and one thing led to another. A mutual friend introduced us, and I’d see him when he was in New York. I think he liked me because he’d never met a Jew who drank as much as I did.”

Sinatra was always more cynical about the Hollywood press corps. He thought most of them were freeloaders, or on the take. “I’ve seen the bills, baby,” he said once about reporters and columnists who took money from the publicity budgets of the studios. In his early years he had cooperated with the fan magazines and other components of the Hollywood publicity machine. At some points he had even groveled to the more powerful columnists when advised to do so (although the most powerful columnist of all, Walter Winchell, never joined in the attacks on Sinatra). But from the mid-1950s until his death, he worked with the press only on his own terms.

“The New York guys are different,” he said. “Maybe because there’s so much else going on around them, they don’t have to cover me. Ah, shit, I like their company. It’s as simple as that.”

Maybe it was, but I doubt it.

IV. Jimmy Cannon, Murray Kempton, and William B. Williams are dead. So are Jilly Rizzo and Sugar Ray Robinson and all those others who once seemed so vividly alive that I could not imagine them leaving the world. Now Sinatra is dead too, and it’s like a thousand people have just left the room.

And yet the tale of Frank Sinatra isn’t only about Clarke’s and Hollywood and Las Vegas; the life he led in such places is part of the tale, but it would be meaningless without the art. Sinatra’s art can be experienced in the 1,307 recordings he made in studios from 1939 to 1995, in the recordings of his concerts, in his videos and movies. In the saloons of the city, you could see what Sinatra had become. But such evenings could never explain the long existential saga of a life entwined with art. He was, in some ways, as elusive and mysterious as Jay Gatsby, not simply to those who knew him but to himself. The keys to the life and the art can only be found somewhere back in the vast obscurity beyond the city.