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May 2024
30min read


AT ZITO’S BAKERY ON BLEECKER STREET, a Greenwich Village institution, there are two framed photographs on the wall behind the counter. One is a picture of the Pope. The other is a picture of Frank Sinatra smiling broadly and holding a loaf of Zito’s bread.

Directly after every baseball game the Yankees win at Yankee Stadium, the public-address system plays Sinatra’s recording of “New York, New York.” When the Yankees defeated the Atlanta Braves in the sixth and final game of the 1996 World Series, capping an improbable comeback from a two-games-to-none deficit, it seemed as if everyone in the stadium was singing along, swelling the final chorus: “And if I can make it there, I can make it anywhere,/It’s up to you,/New York, New York.” The aging Sinatra—he was in his sixties when he recorded “New York, New York,” the last of his blockbuster hits—does amazing things with the initial And in the lines just quoted, twisting and turning the word as if it contained not one but three or four syllables; the voice seems to go down a valley and come back up a hill on the other side. The gesture is inimitable though it also invites imitation, and watching a Sinatra fan trying to duplicate the effect can be very entertaining. Here it was the instrument of joyous release. Here you had a crowd approaching 60,000 people getting into the act. It was a great moment of New York solidarity, and it was also in its way an expression of Frankophilia, the populace’s love for the greatest of all popular American singers.

Few people, and fewer nonathletes, know what it feels like to bring 60,000 cheering fans to their feet. Sinatra had that power. It was (and still is) his voice that thousands of men hear coming out of their mouths in the shower. His is the voice of cities: “New York, New York” at Yankee home games (and in the closing credits of Spike Lee’s Summer of Sam). “My Kind of Town” at Chicago’s United Center, where the Bulls of Michael Jordan held court and which Sinatra officially opened with one of his last live concerts. And“Chicago” (“that toddlirf town”) in the Chicago Cubs’ venerable Wrieley Field.


In each case it is not precisely the song itself but the Sinatra version of the song that has established itself as our public voice, the surrogate voice of the man in the street, the fan, the voice of heroes but also of losers, mutts, and sobbing drunks. This is true of a great many songs. Thus we have records like Keely Sings Sinatra (2001), featuring Keely Smith singing “My Way” and “It Was a Very Good Year,” and Tony Bennett’s Perfectly Frank , which includes “One for My Baby” and “Angel Eyes.” A favorite CD of mine, Blue Note Plays Sinatra (1996), consists of jazz treatments of Sinatra songs. There’s Art Blakey and the Jazz Messengers with “Come Rain or Come Shine,” Freddie Hubbard with “All or Nothing at All,” Dexter Gordon with “Guess I’ll Hang My Tears Out to Dry,” Cannonball Adderley with “Dancing in the Dark,” Sonny Rollins with “I’ve Got You Under My Skin,” The Three Sounds with “Witchcraft” and “It Was a Very Good Year,” Jacky Terrasson with “I Love Paris,” Miles Davis with “It Never Entered My Mind,” Ike Quebec with “Nancy (With the Laughing Face),” Bennie Green with “This Love of Mine,” and Joe Lovano with “Angel Eyes.” In what sense are these Sinatra songs? Except for “This Love of Mine,” for which he wrote the lyrics, Sinatra wrote none of them, but he sang them so well that they are forever associated with him. Seldom can a performing (or interpretive) artist lay claim to such an almost authorial relationship to material someone else composed.

In the Hollywood version of Guys and Dolls (1955) Marion Brando plays Sky Masterson and Sinatra plays Nathan Detroit. Conventional wisdom has it that both are miscast, because Masterson has to do more singing and Brando does not have the better singing voice. I happen to like Sinatra’s performance as Nathan Detroit, who runs “the oldest established permanent floating crap game in New York.” It’s a persona he would relish in the first of the Rat Pack movies, Ocean’s Eleven (1960), a comic caper in which Sinatra and company (Dean Martin, Sammy Davis, Jr., Peter Lawford, Joey Bishop, et al.) conspire to rob five Las Vegas casinos simultaneously. In Ocean’s Eleven , Angle Dickinson, playing Sinatra’s estranged wife, tells him that he “could never love a woman the way you love danger.” What he leads is “not a life, it’s a floating crap game.”

Sinatra, who wanted the role Brando got in Guys and Dolls , did go on to record Sky Masterson’s best song, “Luck Be a Lady,” triumphantly in 1963. But the linkage of Brando and Sinatra at the top of the ticket in Guys and Dolls marks a confluence too rich to go unremarked, because Sinatra is to singing what Brando is to acting: a method actor, who doesn’t just sing a song but lives it. He inhabits a song the way Brando inhabits the roles of Stanley Kowalski, the rebellious biker in The Wild One , Terry Malloy in On the Waterfront , and Don Corleone.

Sinatra has, one could say, narrative ability. He turns a song into an intimate, seemingly autobiographical short story, usually a love story as told from the heights of romantic excitement (“I’ve Got the World on a String”) or the depths of romantic despair (“I’m a Fool to Want You”). At an academic conference devoted to Sinatra at Hofstra University in November 1998, the year of his death, Julius LaRosa (who sang on Arthur Godfrey’s TV show in the 1950s) chose Sinatra’s version of “I Get a Kick Out of You” to illustrate the singer’s narrative approach. “He sang the song not as it is written, not as a band or dance song, but as a song with a story to tell,” LaRosa said. On another occasion LaRosa remarked that Sinatra could “turn a thirty-two-bar song into a three-act play.”

It happened fast. In 1939 Sinatra began the year singing at the Rustic Cabin in Englewood, New Jersey. In the years since, maybe a million people claim to have heard him perform there. One person who really did hear him was handsome Harry James, of the mustache and trumpet, who signed the singer to a oneyear contract at $75 a week. With the James band Sinatra sang “It’s Funny to Everyone but Me” in August and “All or Nothing at All” in September. The voice was creamy, smooth, with a vulnerable edge. Sinatra, Pete Hamill writes, “created a new model for American masculinity,” and this was apparent from the start. So was the singer’s countervailing confidence, even defiance. James (whose signature song was “You Made Me Love You") wanted his new boy singer to change his name to Frankie Satin. Screw that. His mother would kill him. He was Frank Sinatra, and he would stay that way. Years later, when the subject of the proposed name change came up, Sinatra cracked, “If I’d done that, I’d be working cruise shins today.”

Sinatra is to singing what Brando is to acting. He doesn’'t just sing a song but live it.

“When Frank joined the band,” James said, “he was always thinking of the lyrics. The melody was secondary. If it was a delicate or pretty word, he would try to phrase it with a prettier, softer type of voice. … He could sing the wrong melody, and it would still be pretty.” By the end of 1939 Tommy Dorsey, “the sentimental gentleman of swing,” had heard Sinatra on the radio and hired him away from James for his own vastly more successful band. He raised Sinatra’s salary to $125 a week. Sinatra would replace Jack Leonard, a fine crooner (“Marie,” “In the Still of the Night”), who had left the Dorsey band to strike out on his own and had flopped. Sinatra had just turned 24.


Sinatra hated leaving the James hand. The last night was in Buffalo in January 1940, and Sinatra never forgot it. “The bus pulled out with the rest of the guys after midnight. 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 of the bus disappear. Then the tears started, and I tried to run after the bus.”

At a party, I was having a conversation with a friend about our favorite Sinatra songs. I chose “I’ve Got You Under My Skin” (1956), and he countered with a different Cole Porter tune, “At Long Last Love” (1957), although he said he was tempted by “I Get a Kick Out of You” (1953), because of Sinatra’s marvelous riff on the final you , or “Night and Day” (1957), which has another of those amazing Sinatra moments, when he stretches the word through in the phrase “and this torment won’t be through / until you let me spend my life making love to you.”

What do all four of these songs have in common? They were composed by Cole Porter, whose urbanity and wit made him perhaps the ideal composer for Sinatra, with Richard Rodgers of Rodgers and Hart a close second, followed by George Gershwin, Duke Ellington, Harold Arlen, Jerome Kern, and Irving Berlin, possibly in that order. Sinatra is the exemplary interpreter of the great American songbook because he can shade his emotions. His joy is edged with irony and also sometimes with rue, melancholy, and something more, a heartbreak bred in the bones.

Perhaps even more important, all four songs were arranged by a former trombonist with the Dorsey band, a genius named Nelson Riddle. Working with Riddle was one of the best things ever to happen in Sinatra’s career. Riddle helped define the Sinatra sound during the eight years he sang on the Capitol label, the period of his best work, 1953 to 1961. If you’re a newcomer to Sinatra, I recommend beginning with The Capitol Years , a three-CD anthology set, and then going on to these indispensable individual albums, all of them with Riddle arrangements: Songs for Swingin’ Lovers!, In the Wee Small Hours, A Swingin’ Affair, Swing Easy, Nice ’n’ Easy, Only the Lonely, Close to You .

Will Friedwald: “It remained for Riddle to develop both the ballad side and the swinging side of Sinatra, or rather to extend the legacies of Axel Stordahl and George Siravo and, before him, Sy Oliver. And the Sinatra-Riddle sound has since become what we think of when we think of Sinatra; the pre-Riddle period can be reduced to a prelude, the post-Riddle era to an afterthought.”

Bobbysoxers loved him for his androgyny.

During the Capitol period Sinatra’s voice is no longer quite as impressive or as naturally pleasing as when he was known as “the Voice.” It has lost range; he now has to strain for high notes. It has been roughened by experience and by all the cigarettes he has smoked. (“The cigarettes you light, one after another, / Won’t help you forget her, and the way that you love her”: “Learnin’ the Blues.”) The voice has grown deeper, fuller, older. The boyishness that showed in the songs he recorded with the Harry James and Tommy Dorsey bands is long gone. The paradox is that Sinatra in the 1950s hasn’t as great a voice and yet is a greater singer. The difference lies in his command of fast tempos in such Riddle-arranged masterpieces as Songs for Swingin’ Lovers! (1956) and A Swingin’ Affair (1957). But the superiority of the fifties Sinatra extends to ballads also, because he now seems to have perfected the uncanny ability to make a song come to life, to turn it into a chapter of his autobiography, as when, accompanied by a lone piano, he lights a cigarette and sings “One for My Baby (and One More for the Road),” which gets a lot of people’s votes as Sinatra’s greatest saloon song.

Oh, yes—you wanted to know the meaning of swing , the word that recurs so often in Sinatra’s album titles? Listen to “All of Me” on Swing Easy (1954). This is a song Sinatra sang frequently in the 1940s, each time experimenting a little more with the phrasing and with how he exits from the song. Here he sings the final stanza with such exuberance as to undo the actual sense of the words; it’s what is meant by “kidding the lyrics.” Where the line as written would require him to sing “can’t you see, I’m no good without you,” he sings “can’t you see, I’m just a mess without you.” The emphatic mess sounds more like a triumphant declaration of independence than a suitor’s plea. The lyrics say one thing, the delivery says another, and the style makes it cohere. That’s one way swing works.

When Sinatra was Dorsey’s boy singer, he approached the editor of Metronome and lobbied to be put on the cover. “There’s only Crosby and me, and he won’t be around forever,” Sinatra said.


After Sinatra died, I overheard somebody say that he was overrated: “Without his voice he would have been nothing.” There must be a rhetorical term for such a statement.

“Sinatra’s voice went through range changes. His sound changed. He went from the violin with Axel [Stordhal, Sinatra’s primary arranger in the 1940s], the pure violin sound, to the sound underneath, the viola, with Nelson [Riddle]” (lyricist Sammy Cahn). “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” (Pete Hamill).

Early on, Sinatra’s baritone borders on the tenor. He sings with ease though never quite as effortlessly as Crosby. He sings with unusual tenderness and the ability to express longing and aspiration and heartbreak. He also articulates the lyric with absolute clarity. He has amazing range: His deep, rich baritone can reach sublime heights and can sustain the note, thrillingly, as at the end of Jerome Kern’s great love song “All the Things You Are” (1944).

Already in his first recordings you get a sense of that narrative ability, his way of turning a lyric into a short story. Songs like “Falling in Love With Love” (Rodgers and Hart) and “Stormy Weather” (Harold Arlen) and “Where Is My Bess” (Gershwin) and “Fools Rush In” (lyrics by Johnny Mercer) turn into dramatic events, stories that unfold in a performance that combines marvelous singing and a natural gift for (method) acting.

Listen to “I’ll Never Smile Again” (1940), Sinatra’s first major hit with Dorsey. Sinatra and the Pied Pipers, the band’s vocal group (among them Jo Stafford), begin the song with a chorus (“I’ll never smile again / Until I smile at you. / I’ll never laugh again”), and then Sinatra alone and unadorned completes the quatrain: “What good would it do?” When you hear him sing this line, you will understand right away why the first of his nicknames was “the Voice.” Later, in the Rat Pack days of the 1960s, he became “Chairman of the Board,” the guy who had his own record company, Reprise, and could make anything—well, just about anything—happen. When he came back from retirement in the 1970s, he refashioned himself as “Ol’ Blue Eyes.” But in the 1940s he was the Voice, who could ascend to the summit of high notes and stay there, as at the end of “Ol’ Man River” (1945). Jerome Kern, who wrote the music for “Ol’ Man River,” said, “My idea with that song was to have a rabbity little fellow do it—somebody who made you believe he was tired of livin’ and scared of dyin.’ That’s how you do it, Frankie.”

Sinatra expressed regret without selfpity, pain with no loss of masculinity. The poet Carolyn Kizer reasons that the bobbysoxers of the 1940s lost their hearts to young Frankie because he was androgynous, combining masculine and feminine traits, his big voice coming out of his undernourished body. As Crosby sang in a comic 1944 duet with Sinatra, “How can that voice come out of nowhere?”

Sinatra was the first boy singer to prompt mass teenage female hysteria. The breakout event took place three months after the singer had left the Dorsey band. He wanted to make it on his own, not as part of someone else’s Big Band. In a life of gambles this was a spectacular one. On December 30, 1942, Benny Goodman and his sextet were performing at the Paramount Theater in New York. Sinatra’s solo performance was the last act. The singer began and the girls let out their shrieks. Goodman was startled. “What the f— was that?” he exclaimed. That was the moment the Frank Sinatra “phenomenon” began.

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

When Sinatra joined Tommy Dorsey, Jo Stafford noted how thin he looked, “almost fragile-looking. When he stepped up to the microphone, we all smirked and looked at each other, waiting to see what he could do. The first song he did was ‘Stardust.’ I know it sounds like something out of a B movie, but it’s true: Before he’d sung four bars, we knew. We knew he was going to be a great star.”

With the Dorsey band, Sinatra and Connie Haines and the Pied Pipers sang “Oh! Look at Me Now” (1941), a great upbeat number that has a crucial role in the allegory of Sinatra’s career. It expresses the exultation of having arrived, just as “All or Nothing at All” (1939) states the uncompromising nature of the singer’s propositions and personality. Sinatra sings “Oh! Look at Me Now” with great gusto on A Swingin’ Affair (1957).

Another allegorical Sinatra title is “Why Try to Change Me Now?” (1952), the last recording he made for Columbia Records, with whom he had recorded ever since striking out on his own in 1943. The song is widely interpreted as a parting shot at Mitch Miller, Columbia’s chieftain, with whom Sinatra had long feuded. In September 1953 Sinatra was overheard on the phone saying, with characteristic bravado, “Hey, I just fired Columbia.” What happened was a little more complicated: Columbia had decided to drop him, and the feeling of good riddance was mutual. But Sinatra and his fans never forgot the idiotic novelty songs that Miller obliged him to cut (“Mama Will Bark”), and in Las Vegas many years later, when Miller offered to shake hands, the seated Sinatra, surrounded by friends, looked up and said, “F— off.” Sinatra was great at holding a grudge.

The battle of the baritones: If I were a disc jockey, I would begin an hour by playing Jack Leonard (“In the Still of the Night”), then Perry Como, Bob Eberly (“Brazil”), Vie Damone maybe, definitely Dick Haymes (“It Might as Well Be Spring”), Mel Torme (“That Old Feeling“), saving Sinatra for last (“Imagination”). After a break I’d play something by Crosby, the gold standard of the period (though I’d probably pick a Crosby recording of the previous decade, “Pennies From Heaven”). I think I’d also play a song Sinatra sang about three of his rivals who were “breathing on [his] neck.” “Dick Haymes, Dick Todd, and Como,” a parody of the nowobscure “Sunday, Monday, and Always,” had lyrics specially written by the Sinatra loyalist Sammy Cahn. The song appears on the V-discs Sinatra cut for U.S. troops during World War II. When, in the middle of the song, he substitutes “Perry” for “Como” and in a spoken aside says, “That’s the other guy’s first name,” you grasp in an instant the difference between Sinatra the voice and Sinatra the mouth. The singer’s voice was the voice of an angel, pure in diction. But the mouth was always Hoboken. The song ends: “There’s room for all of us. / There’s just one Crosby. / There’s room for all of us.”

He described the Rat Pack as “just a bunch of millionaires with common interests.”

Before his first solo performance at the Paramount, Sinatra told Johnny Mercer, “I’m going to sing Bing’s ass off.”

From Tommy Dorsey, Sinatra learned a critical lesson in breath control: how to stretch a note, or link the last note of one phrase with the first note of the next. Sinatra worked hard at it. He swam for hours in swimming pools, frequently underwater, to develop this capacity. Earlier, Harry James had encouraged him to learn to jump rope.

With the Dorsey band he sang “Polka Dots and Moonbeams” and “How About You?” and “I’ll Be Seeing You” and “Without a Song.”

Dorsey’s theme song was “I’m Getting Sentimental Over You.” But Dorsey was anything but sentimental in matters of money. When Sinatra went out on his own, Dorsey forced him to sign a punitive contract that would grant Dorsey a percentage of all of the singer’s future royalties. Sinatra thought it worth the risk. Later he managed to slide out of the contract altogether, though it cost him a considerable amount of money and more. It resulted in a terminal fallingout between bandleader and singer. “I hope you fall on your ass,” Dorsey told the singer. Dorsey wanted Sinatra to fail, and Sinatra never fully forgave him, though he did turn up unannounced to toast the bandleader and sing at a memorable Dorsey tribute in New York in February 1955. (If you can find the CD called This One’s for Tommy , featuring Sinatra and Jo Stafford, buy it.) Years later—June 1979, in Los Angeles—Sinatra introduced Harry James to a live audience: James was a great guy. James had let him out of his contract after only six months. “And then there was Tommy Dorsey,” Sinatra said. “And when I wanted to get out of my contract to him, it cost me seven million dollars.” Suddenly the specter of Tommy Dorsey materialized before him as a ghost to a Shakespearean prince. “You hear me, Tommy? You hear me? I’m talking to you.”


Sinatra’s favorite toast: “May you live to be a hundred, and may the last voice you hear be mine.”

In The Godfather (1972), Michael Corleone (Al Pacino) explains to his girlfriend Kay Adams (Diane Keaton) how his father had liberated the famous singer Johnny Fontane (Al Martino) from the punitive contract a bandleader had made him sign as a precondition for allowing him to leave the band. “My father made him an offer he couldn’t refuse,” Michael says. “Luca Brazzi held a gun to his forehead and my father assured him that either his brains or his signature would be on this sheet of paper.” Because of The Godfather , many people believe (erroneously) that Sinatra landed the part of Maggio in From Here to Eternity —his comeback part, which saved his career—because a Mafia boss dispatched a thug to decapitate a stallion and put the bleeding head in the resistant film director’s bed while he slept.

Of how many songs is it true that Sinatra’s version is definitive? Of “I’ve Got You Under My Skin,” certainly, where Sinatra’s perfectionism required 22 takes on January 12, 1956. Many fans (I am one) think this the greatest of Sinatra’s finger-snapping up-tempo songs, with a wondrous instrumental bridge featuring Milt Bernhart’s inspired trombone riff. It was true of “Saturday Night Is the Loneliest Night of the Week” during World War II, of “Witchcraft” in the late 1950s, of the incomparable saloon songs “One for My Baby (and One More for the Road)” and “I’m a Fool to Want You,” and of nearly all the “all” songs that Sinatra turned into standards: “All or Nothing at All,” with the Harry James band, which sold 8,000 copies when first released in 1939 and a million when rereleased years later; “All the Things You Are,” on the Columbia label in 1943, with its climactic mile-high last note; “It All Depends on You,” as arranged by George Siravo in 1949; “All of Me,” as arranged by Nelson Riddle for Capitol in 1954; and “All the Way” (1939), which played in the background when the college men of a previous generation did their best to bed their girlfriends.

Sinatra sang the novelty songs that Americans used to love, such as “High Hopes,” which (with changes in wording) became John F. Kennedy’s campaign theme song in 1960. As a 12-year-old boy caught up for the first time in the excitement of presidential politics, 1 well remember the new lyrics Sammy Cahn fashioned:

K- E- double-N- E- D- Y, Jack’s the nation’s favorite guy, Everyone wants to back Jack, Jack is on the right track. And he’s got high hopes, He’s got high apple-pie-in-the-sky hopes …

In 1997 a man accused of threatening to kill a former lover seemed to conduct himself according to the lyrics of Sinatra songs. Interviewed by a journalist in a diner, he sang variants on “My Way” to summarize his situation. On his former lover’s answering machine he sang “This Love of Mine” in an attempt to reconcile. (Did he know Sinatra had composed the lyrics of “This Love of Mine"? Probably not.) On the other hand, when the Apollo 11 astronauts orbited the moon in July 1969, they beamed Sinatra’s “Fly Me to the Moon” back to earth.

Humphrey Bogart was the center, and Sinatra a member, of the original Rat Pack. After Bogart’s death in 1957, Sinatra— “with his natural charisma and inability to be alone” (James Wolcott, Vanity Fair )—found himself at the center of a group that included, besides Bishop, Davis, Lawford, and Martin, the actresses Angie Dickinson and Shirley MacLaine and such others as Milton Berle and Sammy Cahn. “There is no such thing as a clan or pack,” Sinatra explained. “It’s just a bunch of millionaires with common interests who get together to have a little fun.”

“It was Sinatra who triangulated Hollywood, Washington, and the Mafia” (Wolcott). His Rat Pack pal Lawford, the British-born actor who had married President Kennedy’s sister Pat, introduced Sinatra to Sen. John F. Kennedy in the late 1950s. Like the singer, the senator enjoyed partying in Las Vegas casinos. Following one of his performances at the Sands, Sinatra introduced the by then presidential candidate John Kennedy to Judith Campbell. It happened during the period of the filming of Ocean’s Eleven , the quintessential Rat Pack movie. Sinatra arranged a roomservice lunch for Kennedy and Campbell in his private suite. And thus began a two-year affair that continued after Kennedy occupied the White House and despite the President’s awareness that Campbell had become the mobster Sam Giancana’s moll. All this we know from FBI files, which Sinatra obtained in 1981 under the Freedom of Information Act and which were edited for book publication under the title The Sinatra Files by journalists Tom and Phil Koons in 2000.

He put all the misery of his relationship with Gardner into “I’m a Fool to Want You.”

Giancana and his associates thought they had a line into the White House. They expected that the Kennedy administration would, in exchange for electionyear favors, go easy on Mob activities. They hadn’t reckoned on Robert F. Kennedy’s righteous moral indignation, which took the form of the Attorney General’s holy crusade against organized crime. Besides hating the brothers Kennedy, Giancana was furious with Sinatra (whom he called “the canary") for failing to exercise his supposed influence with the young President. Federal wiretaps caught a conversation between Giancana and Johnny Formosa, a henchman. “Let’s hit Sinatra,” Formosa said. “Or I could whack out a couple of those other guys, Lawford and that [Dean] Martin, and I could take the nigger [Sammy Davis, Jr.] and put his other eye out.” It is said that Giancana decided against whacking the canary because he wanted to hear him sing “Chicago” one more time.

It is difficult to write about Sinatra not only because a million other guys have the same ambition and gallons of ink have already been spilled but because he was more than a singer. What he stands for is complicated: a charmed life, maybe; stylishness; his ability to put over a song, to make it seem like an extension of his own personality and experience; the fascination of an intense and contradictory personality, the self-described "18-karat manic-depressive,” a wounded swinger who could consort with Presidents and gangsters, but who also liked painting and took photographs at the first Ali-Frazier fight that were good enough for Life magazine to run. The trajectory of his career extended from Roosevelt to Reagan, from the Big Band era that he helped bring to an end by going solo successfully in 1942 to beyond the boozy Las Vegas casino scene of the go-go 1960s. He went nightclubbing with JFK, performed at the Nixon White House, took tea with Nancy Reagan when her husband was President. He had also participated in the common citizen’s love of FDR. (In the version of the great Vernon Duke-Ira Gershwin standard “I Can’t Get Started” that he sings on the album No One Cares , in which the speaker’s worldly success is contrasted with his failure to win the girl, Sinatra sings this marvelous couplet: “Each time I chanced to see Franklin D. / He always said ‘Hi, buddy,’ to me"). Nancy Sinatra, with whom he sang the forgettable topof-the-charts hit “Somethin’ Stupid” in the late 1960s, said that trying to define her father was like trying to analyze electricity. He had a flair for the dramatic and an instinct for stage center. A fingersnapping Lazarus in a tux, he took a punch, went down, and then got back on his feet and won the fight.

In the 1940s Sinatra had hit record after hit record. He liked the taste of Hollywood glamour and learned to dance well enough to serve as Gene Kelly’s junior partner in sailor-suit movies like On the Town and Anchors Aweigh . And then his career came crashing down. He was photographed with gangsters in Havana in February 1947. He punched out the obnoxious Hearst columnist Lee Mortimer in April 1947 and did other things that earned him the enmity of the fourth estate. He conducted a very public love affair with Ava Gardner, then possibly the most beautiful woman in Hollywood. She and Sinatra fought constantly, histrionically. Female fans deserted him just as he had deserted his wife and children. He would lose his radio show, would jeopardize his recording contract with Columbia. In 1950 his voice failed him in public; he opened the mouth to sing and nothing came out. He was told that he suffered from vocal cord strain and that the only way to get better was not to sing.

For Ava Gardner, the love of his life, Sinatra was willing to risk everything. The affair wrecked his marriage, his health, and his reputation. There are photographs of him with Ava that make it seem they are having the time of their lives. They married in 1951, but it was no honeymoon. Yet the couple’s bitter quarrels seem to have added to the sexual intensity of the relationship.

“We would be sitting in the living room and hear them upstairs in the bedroom quarreling and arguing. Ava would scream at Frank and he would slam the door and storm downstairs. Minutes later we’d smell a very sweet fragrance coming from the stairs. Ava had decided she wasn’t mad any more, and so she sprayed the stairwell with her perfume. Frank would smell it and race back up to the bedroom. Then it would be hours before he’d come back down” (Betty Burns, wife of Sinatra’s manager at the time, quoted by Kitty Kelley).

Sinatra put all the misery of his relationship with Ava into “I’m a Fool to Want You” (March 27, 1951), a lonely masterpiece that came out of the nadir of his career.

A Sinatra exit line during one of his fights with Ava: “Swell. You just go off with your sister, and I’ll be in Palm Springs f—ing Lana Turner.”

Ava on Frank: “Frank weighed only one hundred and twenty pounds, but one hundred and ten of them were pure c—k.”

On a visit to Mount Holyoke College in 1992 I was invited to tea by the writ- ers Brad Leithauser and Mary Jo Salter and discovered they are big Sinatra fans. Brad played the Swing Easy and Songs for Young Lovers albums. He took a special delight in Sinatra’s handling of Ira Gershwin’s lyric in “A Foggy Day,” especially his unexpected staccato fivetime iteration of shining in the verse, “And in foggy London town, the sun was shining (shining shining shining shining) everywhere.”

My own favorite Sinatra moments: In “I’ve Got You Under My Skin” (1956), what he does with you in “though each time I do / just the thought of you"; in “It All Depends on You” (1949), the improvised bebop scatting when the title phrase returns after a fantastic tenor-sax solo by Wolf Taninbaum.

In the magazine Callaloo in 1999, Reuben Jackson, the archivist of the Smithsonian’s Duke Ellington and Ella Fitzgerald collections, published his obituary poem “Frank,” which begins:

like god or miles, no second name is needed.

Jackson singles out “In the Wee Small Hours of the Morning,” the title cut on the album of that name, “its longing / unpretentious / and haunting as / moonlight.” He also characterizes the song as “a 32-bar ashram.”

I asked several other writer friends whom I knew to be jazz buffs to pick a favorite Sinatra moment and comment on it. “I love Sinatra,” Phillip Lopate wrote, “and what springs to mind is his version of ‘It Never Entered My Mind,’ where he makes the most of the great lyrics, largely because his voice is best at rue and regret. When he sings, ‘Now I even have to rub my back myself,’ there’s a nice touch of humor in the way his voice rises to suggest the awkwardness of the situation. His maudlinness is under control; it’s a very balanced and sane expression of all we take for granted and then lose.”

The poet Michael Burkard spoke of the moment in “I Get a Kick Out of You” “where in the second verse when he says ‘terrifically’ he prolongs the ifffffff and sounds like he is sniffffffffing cocaine (even though he is sure it would bore him ‘terrifically too’).”

The U.S. poet laureate Billy Collins, whose poems are filled with references to jazz musicians: “I like the way he and only he says ‘chick’ and ‘dame.’”

Lloyd Schwartz, who won the Pulitzer Prize for his music criticism in 1994: “One of Sinatra’s greatest performances is his now-famous ‘unreleased’ 1958 version of ‘One for My Baby’ (ultimately issued in 1990 on The Capitol Years ). Instead of the expected, conclusive ‘that long, long road,’ he trails off—with heartbreaking resignation-singing ‘the long… that long… it’s long.…’ Rodgers and Hart’s ‘It Never Entered My Mind’ (In the Wee Small Hours, Capitol, 1955, arranged and conducted by Nelson Riddle) was a song waiting for Sinatra. As in most of Lorenz Hart’s lyrics, the subject is really language itself—how turns of phrases mirror the inevitable, if unexpected, and mostly unwelcome, twists our lives take:

Once I laughed when I heard you saying That I’d be playing Solitaire, Uneasy in my easy chair. It never entered my mind.

“‘Once.’ Sinatra’s voice carries the narrative wonder of ‘once upon a time,’ only here it’s more personal, more real. This happened—but how could it? His long pause after playing points up the internal rhyme with saying , but, more important, underlines the isolation of solitaire . Then a smaller catch squeezes unsettlingly between un - and an uneasily stretched-out, tonally wavering easy.

“He then eases into the long ee of easy chair , both caressing and bending the note so that it captures not only the seductiveness of the chair, that haven of comfort it never occurred to him he could lose, but also his current squirm of discomfort, ache of regret. The wry wordplay makes the enormity of this loss somehow both more and less bearable. As the poet Elizabeth Bishop wrote, with merciless self-irony, sharing with Lorenz Hart her ‘one art,’ the attempt to keep despair at bay through writing, ‘The art of losing isn’t hard to master.’ Sinatra has always been a master of that art.”

He solo success spelled the doom of the Big Band era—and he went on being Sinatra when rock’n’ roll conquered the airwaves.

In 1951 and 1952, Sinatra’s records weren’t selling. His voice had failed him. His TV show was canceled. His marriage to Ava had begun to disintegrate, and he had lost his Columbia contract. He was through in Hollywood too. But as Pete Hamill notes, the fall was central to his legend, for American men respect nothing more than the guy who gets up off the mat after being knocked down. He had to die onscreen for this to happen, in From Here to Eternity , which was like penance for his having been 4-F during the war (a punctured eardrum) and for the fact that his voice had seduced the lonely wives and girlfriends of servicemen abroad. As Private Maggio in Fred Zinnemann’s celebrated film of James Jones’s Pearl Harbor novel, Sinatra got to transform his image. He was no longer the young crooner with the hysterical effect on teenage girls. In the movie he played a tough little ItalianAmerican guy with a lot of pluck and a lot of life, an indomitable private with the singer’s own dems-and-dose Hoboken-ain’t-broken ethnicity. And when he died onscreen, it was not only a superb job of acting. It was as if the young cocky Sinatra died there with Maggio and a new, weathered Sinatra was born. Indeed, the singer’s voice grew rougher, coarser. Men, who had not cottoned to Sinatra in the forties, now got on the bus. In the 1940s he had sounded effortless, smooth, a boy—a wonder boy, to whom nothing bad could happen. Now he sounded like a man whose heart had been broken but who had recovered to live another day and love another time.

Sinatra won the Academy Award for best supporting actor for his work in From Here to Eternity , and from that moment on it was as if he could do no wrong. He had major hit singles in “Young at Heart” and “Learnin’ the Blues.” On the Capitol label he teamed up with Riddle to make the greatest albums of his career. With Riddle he created the first “concept” album, and possibly the greatest, In the Wee Small Hours (1955). All the songs share a somber mood, sweet though in sadness: Duke Ellington’s “Mood Indigo,” Harold Arlen’s “Last Night When We Were Young,” Hoagy Carmichael’s “I Get Along Without You Very Well,” and a trio of terrific Rodgers and Hart songs, “Glad to Be Unhappy,” “It Never Entered My Mind,” and “Dancing on the Ceiling.”

As the title character in Pal Joey (1957), Sinatra gets to choose between Rita Hayworth and Kim Novak—between, that is, two of the most glamorous sex queens of the 1940s (Hayworth) and 1950s (Novak). When he sings “The Lady Is a Tramp” in the movie and gets to the couplet “She’s broke / It’s oke,” he shrugs his shoulders wordlessly and omits the second line. Many listeners regard this version of that great standard as second only to “I’ve Got You Under My Skin” as Sinatra’s best up-tempo song. In High Society (1956) he sings a “swellegant, elegant” duet with his boyhood idol, Bing Crosby, which Crosby regarded as the best duet he had ever done with anyone. In the same movie, Sinatra makes love vocally to Grace Kelly with “You’re Sensational,” a much better song than “True Love,” which Crosby and Kelly sing, though the latter outsold it.

The bandleader Artie Shaw, master of the clarinet, whose version of “Begin the Beguine” was a big hit in the 1940s, preceded Sinatra as Ava Gardner’s husband. This odd fact insinuates a point. When Sinatra arrived on the scene, bandleaders held the most glamorous position in the music world. Harry James was married to Betty Grable. Benny Goodman was the “king of swing.” If it’s a somewhat cruel irony that Sinatra’s solo success spelled the doom of the Big Band era, the silver lining is that Sinatra went on being Sinatra, snap-brim hat and all, when rock ’n’ roll conquered the airwaves and fedoras went the way of crooners.

The whole psychodrama of male-female relations that is delineated in the fine Rodgers and Hart standard “I Wish I Were in Love Again” ("The sleepless nights, the daily fights, / the quick toboggan when you reach the heights, /1 miss the kisses and I miss the bites, /1 wish I were in love again") is implicit not only in Sinatra’s singing style but in his whole public persona. (Sinatra covers the song on A Swingin’ Affair , 1957.) The Sinatra who gave up everything for Ava Gardner is like Shakespeare’s Antony risking his kingdom for a mirth. He is also the embodiment of the American man as he would like to see himself, a kind of hard-boiled romantic, like Bogart as Sam Spade or Philip Marlowe, acquainted with defeat and failure, a loner who nevertheless can’t stay single but compulsively involves himself with a femme fatale, and every woman is one, a man for whom women are easy in one sense, difficult in another, for whom heartbreak is the flip side of cocksure jauntiness, and melancholy and elation are so closely related it’s hard to tell them apart.

At the Hofstra conference devoted to serious Sinatra studies, Roger Gilbert of the Cornell University English department read a brilliant paper entitled “Sinatra and the Culture of the '50s.” One notion Gilbert pursues is that there are aesthetic parallels between Sinatra and the abstract expressionists (or action painters). “A moment ago I suggested that Sinatra might be called a Method Singer; let me now propose that he be considered an Action Vocalist,” Gilbert said. “Sinatra’s best recordings, like his concert performances, always have the quality of live events, of actions rather than mere recitations. Just as we’re continually aware of [Jackson] Pollock’s choices, his split-second swerves, hesitations, and thrusts as he wields the brush, so in listening to a Sinatra track we hear the impulsive gestures of his voice as it carves its own path through a song. Improvising, ad-libbing, bending, or embellishing a melody, condensing or stretching out a lyric, Sinatra is constantly making choices as he sings, and that’s surely where much of the excitement of his music lies. There’s a tangible riskiness in his best performances, a willingness to leap without knowing exactly where he’ll land. As a result his records sometimes contain clinkers, clams, sour notes, failed effects; but these stand as evidence of Sinatra’s total commitment to the moment in all its unpredictable power.”


Sinatra married Mia Farrow in 1966

when he was 50 and she 21. “I’ve got Scotch older than Mia Farrow,” Dean Martin said. The marriage didn’t last. Years later Sinatra confessed he still didn’t know what that was about.

Parlor game: Which of the four Sinatra wives would you choose to be: Nancy Barbato, his first love, mother of his children, keeper of the family name and flame, to whom he was loyal though not faithful; Ava Gardner, perhaps the most beautiful woman in Hollywood; the young Mia Farrow at the beginning of her career as an actress ( Rosemary’s Baby ) and as a gossip-column stalwart (her subsequent consorts include Woody Alien); or Barbara Marx, who married him when he was old and revered, an institution, indeed a character in celebrated novels (Don DeLillo’s Underworld )? All but Ava Gardner survived him.

Sinatra toured the world giving concerts. He devoted the proceeds of some tours entirely to charity. He made huge amounts of money and gave large sums away. He tipped (he called it “duking") more lavishly than anyone else. After Sinatra died, on May 14, 1998, everyone quoted Dean Martin: “It’s Frank’s world, we just live in it.” When I told a friend, a very attractive and flirtatious woman of 26, that I was working on an article about Frank Sinatra, she said, “Is there a place in it for a photograph of me naked surrounded by Frank Sinatra CDs?”

Today, a rainy cold first day of spring, I went to a dermatologist to check out a minor skin irritation. A first consultation. He asked me what I did and I said I was a professional writer and he asked, “Of what?” and I said, “Well, just now I’m working on an article about Frank Sinatra,” and he lit right up. A real fan, he listens to Jonathan Schwartz’s Sinatra radio show, and Sid Mark’s. When I leave, he thanks me for brightening up the afternoon, and I depart in the rain listening to Sinatra sing “Meet Me at the Copa,” in which more than one defunct New York institution surfaces: “Now there are people who prefer the art museum, / And out in Brooklyn there’s a ball park and a team, / But I don’t care a whole lot if I never see ‘em / Meet me at the Copa, meet me at the Copa tonight.”

Sinatra and women. Dean Martin: “They should put Frank’s zipper in the Smithsonian.” Humphrey Bogart remarked that Sinatra thought paradise was a place that was filled with women and had no journalists but what he didn’t realize was that he’d be better off the other way around.

Everyone wishes Sinatra had chosen his movies as carefully as his songs. But whereas in singing he would put himself and the crew through 22 takes, in making movies he was convinced that the first take was best. Yet he made some very good movies. Among the dramas I would nominate are From Here to Eternity, The Man With the Golden Arm , and The Manchurian Candidate in the must-see category; Ocean’s Eleven (which is far superior to the George Clooney remake) and Robin and the Seven Hoods as interesting for Rat Pack as well as musical reasons; The Tender Trap and Young at Heart , costarring Debbie Reynolds and Doris Day respectively, are underrated amusements of the mid-1950s and have great title tracks; and of the high-production musicals, you’ve got to see On the Town, Guys and Dolls, High Society , and Pal Joey .

He embodies the American man as he would like to see hemself.

Oddly, Sinatra appeared in two movies centering on presidenrial assassinations, Suddenly (1954) and The Manchurian Candidate (1962). Kitty Kelley recounts that when the president of United Artists expressed unease about making the latter, Sinatra went directly to President Kennedy, who said he liked the book and would not object to seeing it made into a movie. “That’s the only way that film ever got made,” Richard Condon, the book’s author, said. “It took Frank going directly to Jack Kennedy.”


Sinatra is the godfather of the HBO hit “The Sopranos.” One season began with Sinatra singing “It Was a Very Good Year.” When Tony Soprano fingers an FBI informant, the fact that the suspect while in prison had made a bust of Sinatra proves vital. When Tony’s father, in a flashback, is in a merry mood, he dances with his wife in the kitchen, singing “All of Me,” Sinatra version (1954). The album Sinatra’s Sinatra (1963) is visually conspicuous in another episode. In still another, Tony and Carmela Soprano tell their children during dinner about the great contributions Italians and Italian-Americans have made to civilization. The list starts with Michelangelo and ends with Tony beaming: “And, of course, Francis Albert.”

Sinatra despised several of his monumental crowd pleasers, including “Strangers in the Night,” which reached the top of the charts in 1966, and “My Way,” which did the same in 1968.

The television dramatization of Sinatra’s life that his younger daughter Tina Brown produced in 1992 starring Philip Casnof is excellent, in my view the best of numerous attempts to adapt Sinatra’s biography, or aspects of it, to the little screen.

The name Sinatra contains in anagrammatic form the words sin, art, rain, trains, stair, satin, saint, stain, artisan, rat, rant, strain, star .

When Sinatra retired in 1971, a decision he would soon reverse, he concluded his farewell performance in Los Angeles on June 13 with “Angel Eyes.” The stage went dark, and he lit a cigarette. “Thanks to stagecraft and the majesty of his singing, Sinatra stage-managed a perfect coda,” Will Friedwald writes. “As he delicately entered a diminuendo, the smoke from his cigarette gradually enveloped him as both the volume and the spotlight grew smaller and smaller. Finally, when Sinatra uttered the last line, “Scuse me while I disappear,’ he was gone.”

When he died, on May 14, 1998, New York lighted the Empire State Building in blue lights in his honor. “That’s power,” a friend said. “No,” I said. “That’s love.”

On December 12,1997, Sinatra celebrated his eighty-second (and last) birthday. I wrote:

There’s an old French saying, “the whole of a man’s mystery rests in his hat,” and if you translate it into American you get Sinatra smoking and singing “Memories of You,” “I Thought About You,” “You Make Me Feel So Young,” and “You Brought Me a New Kind of Love to Me,” all from the same 1956 session, I love that voice and have since the summer I was eight and my friend Ann and I sang “Love and Marriage” on Talent Night at the bungalow colony when I’m down there’s nothing like you, birthday boy, singing “All of Me” to lift me up and when I’m in love I jump out of bed in the morning singing “It All Depends on You” and your voice comes out of my mouth.

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