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Frank Sinatra: the Loneliness of the Long Distance Singer

ISSUE:  Autumn 1999

Enter any music store and ask for the Frank Sinatra section and you can expect two surprises, one obvious, the other less so. The obvious surprise is how many bins of Sinatra compact discs and audiocassettes you will find. Music stores are not museums—they stock what sells. Web sites are a bit more eclectic, but even so it’s a bit startling to enter “frank sinatra” into the “Search” box at, say, and learn that 256 musical items are available for purchase, along with 117 books and 144 videos. To be sure, Sinatra was a prolific and commercially successful musician who had hit records in each of seven consecutive decades, beginning with the 1930’s. But, even so, this is 1999, a good year after his death. And unlike Elvis, unlike Hendrix, unlike Jim Morrison and Janis Joplin and Kurt Cobain, Sinatra was not young when he died: he was 82 years old.

The other, less obvious surprise that awaits the Sinatra hunter in a music store is where his records are kept. They are in the rack called “Easy Listening,” just east of Henry Mancini and just west of the Fred Waring Singers. The assumption seems to be that anything your parents or grandparents listened to when they were young, before the advent of rock, was easy on the ears. But could anything be less easy, more unsettling than hearing Sinatra sing “One for My Baby” or “When Your Lover Has Gone,” music that he called “saloon songs” and that critics described as “suicide music”? In these songs and in many others like them, Sinatra sang about life at the bottom of the abyss. He always sounded like he lived there.

No one could sing of loneliness better than Frank Sinatra— unrequited love, love gone wrong, love lost. Observers without number, noting the contrast between Sinatra’s life—always tempestuous and sometimes violent—and his tender, evocative, and sensitive singing, have wondered with the novelist Barbara Grizzuti Harrison “whether his life springs from one set of impulses and needs and his work from another, whether. . . Francis Albert Sinatra—a man bruised and bruising—is so divided as to be crazy.” In truth, not madness but loneliness is the key to understanding Sinatra, both the man, who dreaded solitude yet so often felt alone in the entourages with which he surrounded himself and the audiences before whom he performed, and the musician. Even his songs of joy—and no one could express unbounded happiness more thrillingly in his singing than Sinatra—were manifestations of his fundamental loneliness. Just as the athlete who crouches the lowest can jump the highest, so could the singer who sank most deeply into despair express the exhilaration of temporary release from the demons that plagued him more convincingly than anyone else.


The wellspring of the great river of loneliness that ran through Frank Sinatra’s life is not hard to find: he was an only child in a first-generation Italian-American family. Sinatra was born in Hoboken, New Jersey, a city densely populated with immigrant Catholics of one ethnicity or another, in 1915, long before American Catholics had come to regard birth control as an acceptable (or even an available) option. Virtually every lad in the neighborhood was one of five or six or nine; Francis Albert, almost uniquely, was alone. The journalist Pete Hamill, in his research for Why Sinatra Matters, found that “Old-timers from Hoboken would remember him later as a lonely boy, standing in the doorway of his grandmother’s building, watching life go by without him.” Sinatra himself told Hamill, “I used to wish I had an older brother that could help me when I needed him. I wished I had a younger sister I could protect.” It could not have helped that his parents had wanted a girl instead of a boy.

To make matters more exceptional (and worse) for the young Sinatra, not only did his father work long hours, so did his mother. Dolly Sinatra was a leading cog in the Hudson County political machine of Frank (I Am the Mayor) Hague. Extraordinarily for her time (women could not yet vote), Dolly was named leader of the Third Ward in Hoboken’s Ninth District, in part because of her familiarity with the many dialects of Italian that were spoken in the neighborhood. Her job was to help her poor neighbors in their dealings with city hall, then round them up to vote on election day. Sinatra learned early on that if he was going to spend time with his mother, political gatherings were the place to find her. If he was going to win her attention and approval, singing a song or two at these gatherings was the best way to do it. The first entry in the Frank Sinatra songbook was “The Star-Spangled Banner.”

For Dolly Sinatra, singing was a cute thing her boy did to please a crowd; when Frank got a little older, she and his father wanted him to enroll at the Stevens Institute of Technology and “get a real job.” For Frank Sinatra, singing was what life was all about. Dolly was slow to realize this, but once she did she became his champion. She bought him some rudimentary sound equipment and sheet music, no small assets for a singer looking for gigs at corner saloons and high school dances. By some accounts, Dolly used political influence to get Frank into the local singing group, the Three Flashes, which (as the now-renamed Hoboken Four) was about to make a movie short with amateur-night impresario Major Bowes. She also pulled strings to arrange the landmark 1938 booking at the Rustic Cabin nightclub in nearby Englewood Cliffs that earned Sinatra his first notice as a professional singer.

The Rustic Cabin had two great advantages for an aspiring vocalist: it was convenient to New Yorkers, just across the George Washington Bridge, and it had a live radio hookup to a New York radio station, WNEW. In 1939 Harry James, a trumpet player and the leader of a new big band, heard Sinatra on the radio, drove out to see him, liked “Frank’s way of talking a lyric,” and hired him as his boy singer. In those days singers were not the main attraction in popular music; bandleaders were. The singer sat to the side of the stage and stepped to the microphone for only a few numbers, sometimes alone, sometimes with a girl singer or a singing group. Even on his featured numbers, the singer was more a member of the band than a star. Typically, the band would play a chorus (that is, would play through the melody) featuring an instrumental solo by the bandleader, the singer would sing a second chorus, and the band would come back in full force to close out the number. The premium was on new songs, the assumption being that no one wanted to hear songs they had heard before, except perhaps a band’s signature number. Most of the time, people danced and talked while the band played rather than sat and listened. It was a perfect setting for a young singer to learn his craft—the spotlight on him was bright but not so glaring as to reveal every imperfection.

Sinatra’s big break came in 1940, when he caught the eye of Tommy Dorsey, one of the biggest of the big band leaders. Sinatra learned a lot from Dorsey, especially from his ability to sustain long, seamless, melodic lines in his trombone solos. If Dorsey could, in effect, sing through a brass instalment, Sinatra thought, imagine what a vocalist, who had words as well as melody to work with, could do. The key was breath control: the longer a singer could go without stopping to take a breath, the more natural, even conversational his phrasing of a lyric could be. By making proper use of the microphone (which hardly anyone did), he could save even more breath and shade his interpretation of a lyric with a wide range of nuances.(“I discovered very early that my instrument wasn’t my voice,” Sinatra once said. “It was the microphone. . . . You have to learn to play it like it was a saxophone.”) All the old conventions of popular singing—belt out a few words so that they can hear you in the second balcony, gasp for breath, then belt out another line at the same volume—had been rendered obsolete. Sinatra began swimming underwater and running laps to build up his lung capacity. He closely studied what happened musically when he leaned into the microphone, leaned away from it, sang softly or loudly. A “dese, dem, dose” speaker in casual conversation, Sinatra learned to articulate words with crystal clarity when he sang. Years later, a school in Japan would rely almost entirely on Sinatra records to teach corporate executives to speak American English.

Sinatra left Dorsey after nearly three years, not to join another band but to go out on his own. Sinatra’s gamble (and most regarded it as a longshot bet) was that people would accept the singer as a star, with the band removed to the anonymous background, and that they would sit in their seats to hear him, content not to dance. Songs would follow a new pattern—singer, orchestral interlude, then singer again—and could be performed at any tempo, danceable or not. What is more, the risk-taking Sinatra reasoned, people would be happy to listen to old songs if the songs were good enough. Irving Berlin, George and Ira Gershwin, Harold Arlen, Jerome Kern, Richard Rodgers and Lorenz Hart, Cole Porter—why wouldn’t audiences want to hear their songs again and again if they were sung with a subtlety appropriate to the intelligence of the lyrics and the beauty of the melodies? Sinatra covered his bet by hiring arranger Axel Stordahl away from Dorsey. Stordah’s charts graced nearly all of Sinatra’s mid-1940’s recordings with, in New York Times music critic John Rockwell’s phrase, “a wash of strings and lush, neo-Tchaikovskian arrangements.”

Sinatra carefully assembled a short list of songs for his first big appearance as a soloist, at the Paramount Theatre in New York on Dec.30, 1942—short because he was last on a bill that featured a movie, singer Peggy Lee, two novelty acts (the Radio Rogues and Moke and Poke), and the Benny Goodman Sextet. The irony was that no one heard a thing. “What the hell was that?” is the PG-rated version of what Goodman exclaimed after he introduced Sinatra and was greeted with a wall of ecstatic screams from the bobby sox-clad audience of teenage girls. When the phenomenon repeated itself month after month, even culminating in a 1944 riot by 30,000 girls who could not get into the theatre, writers in magazines such as The New Yorker and The New Republic did their best to make sense of it. The absence of boyfriends, off fighting World War II, was the most common and obvious explanation of “Sinatrauma” (also known as “Sinatramania” and “Sinatrance”) that was offered, but hardly the only one. The ultra-thin Sinatra brought out the maternal urge “to feed the hungry,” said one pundit. He had, “for all his youthfulness, something of a father image,” said another.

Sinatra’s meteoric rise in show business did not affect his sense of himself as a little guy who was still represented politically by the Democratic Party and, in particular, by Franklin D. Roosevelt. He was thrilled to be invited to a White House tea in 1944. “Fainting, which once was so prevalent, has become a lost art among the ladies,” the president told Sinatra. “I’m glad you have revived it.” Sinatra was awestruck: “I thought here is the greatest guy alive today and here’s a little guy from Hoboken, shaking his hand. He knows about everything, even my racket.” Although mainstream entertainers universally shunned partisan politics at this time (why alienate the half of your audience that supports the other party?), Sinatra campaigned widely for Roosevelt in 1944, singing and speaking to audiences all over the country. He told a national radio audience on election eve, “Since [FDR] is good for me and my country, he must be good for all the other ordinary guys and their kids.”


Sinatra turned 29 on Dec. 12, 1944, a month after FDR was reelected. Consider the transformations he already had wrought in American politics, culture, and music.

In the political arena, Sinatra had broken down the barrier between entertainment and politics. Sinatra’s own involvement in politics peaked in 1960, when he devoted the better part of a year to helping John F. Kennedy get elected president, then took a right turn in the 1970’s when he became a Republican activist. More important, however, Sinatra laid the groundwork for what the journalist Ronald Brownstein has called “the Hollywood-Washington connection,” in which “celebrities look to politicians to validate them as part of the company of serious men and women, and politicians look to celebrities to validate them as part of the company of the famous.” In an era of declining political parties, politicians have made the trek to Hollywood for campaign funds and celebrity endorsements a major part of their quest for office. Because of Sinatra, Hollywood’s doors have been open to them.

Culturally, Sinatra had introduced, well, sex into public life. (Do we really need to pretend that those screaming girls were daughters seeking fathers or wannabe mothers seeking to give succor?) It is not clear how he did it. When Elvis Presley and other rock singers provoked Sinatra-like pandemonium in subsequent years, it was obvious that they were reaping what, with their evocative movements, they had sowed. But Sinatra just stood at center stage, clad in jacket and tie, holding the microphone stand as he sang. Yes, the young men were off to war, but the young men had been off to war many times before. Could the response Sinatra evoked have had something to do with the way he sang love songs—as if he meant them, and in such an intimate voice that it sounded as if he meant them for each listener? The screaming girls at the Paramount may not have heard him there, but they did not need to. They already had heard him (and heard him and heard him) at home, on records and the radio. As Will Friedwald notes in Sinatra: The Song Is You, “The first teen idol was also the last one not to pander to his audience.”

Finally, and foremost, by age 29 Sinatra had revolutionized popular singing. A product of the big bands, he ended the big band era by making the vocalist the star. A singer of old songs when the premium was on new ones, Sinatra established the American songbook by performing and recording only the best songs by the best songwriters.(When musicians today refer to the “standards” they are employing a concept that did not exist in popular music until Sinatra invented it.) A child of the era of unamplified belters, who sang everything in short bursts and at top volume, Sinatra mastered the possibilities of breath control and the microphone. He sang as if he was telling a story, in flowing conversational phrases, and with all the subtlety and shading of meaning that melody can add to spoken prose.


Hindsight enables us to recognize these innovations by Sinatra in politics, culture, and music as transformations. None of them seemed that way just half a decade later, in the late 1940’s.

Sexually, not a trace of the passions that Sinatra unleashed in his audiences could be found even a few years after his Paramount appearances. The songs of loneliness and longing that had so moved women and girls during the war now fell on distracted ears—their husbands, boyfriends, sons, brothers, and fathers were home. Equally important, Sinatra’s winsome, boy-next-door appeal foundered on the shoals of his desertion of Nancy Barbato, his girl-next-door wife and the mother of their three young children. Sinatra’s tempestuous and, until they married in 1951, adulterous love affair with the actress Ava Gardner seemed outrageous to masses of Americans, not endearing or even enviable.

Politically, by decade’s end Sinatra’s experience gave every indication of being the exception that proved the old rule that political involvement is the kiss of death for mainstream entertainers. In addition to campaigning for Roosevelt, Sinatra crusaded for civil rights, a cause that had virtually no support among whites at this time. He publicly urged the left-wing progressive Henry A. Wallace to run for president in 1948. He condemned the House Un-American Activities Committee for its pursuit of Communists in Hollywood. Not surprisingly, the ultraconservative Hearst newspaper chain responded by unleashing its columnists on Sinatra, especially Westbrook Pegler, George Sokolsky, and Lee Mortimer. His stormy sexual relationships and willingness to be photographed shaking hands with all sorts of people, including gangsters, gave his critics in the press plenty of ammunition to fire at him. Sinatra was temperamentally incapable of shrugging off insults. “Frank is the most fascinating man in the world,” Dorsey once said, “but don’t stick your hand in the cage.” Sinatra did himself little good by fighting back against the press—sometimes literally, as when he assaulted Mortimer in a nightclub in 1947 and was arrested and successfully sued.

As for music, by the late 1940’s Sinatra’s commitment to excellence in popular singing appealed to a vanishing constituency. Not only did audiences once again want to hear new songs, but now only gimmicky new “novelty” numbers seemed to interest them—”Mule Train,” “Mairzy Boats,” “How Much Is That Doggy in the Window?,” “Come on-a My House.” Frustrated at his sagging record and concert sales, and pressured by his recording label, Columbia Records, to get with the times, Sinatra even succumbed once or twice to the new fashion. But listeners could hear his contempt for schlock like “Mama Will Bark” and “My Cousin Louella” in his singing, and they interpreted what they heard as contempt for them. In 1952 Columbia decided not to renew Sinatra’s contract. He also lost his movie contract with Metro-Goldwyn-Mayer, his radio and television shows, and his agent.

No one had ever fallen farther, faster in the entertainment world than Frank Sinatra had. His marriage with Ava Gardner made him miserable; their breakup soon afterward left him feeling worse. Although Sinatra signed with a new label, Capitol Records, he did so on the most unfavorable terms—at first, he even had to pay for his own recording sessions. Sammy Davis, Jr., whom Sinatra had befriended in the early 1940’s, remembered catching a glimpse of him in 1948: “Frank was walking down Broadway with no hat on and his collar up, and not a soul was paying attention to him. This was the man who, only a few years before, had tied up traffic all over Times Square. Now the same man was walking down the same street, and nobody gave a damn.” Two years later, Sinatra’s longtime publicist, George Evans, told a columnist, “Frank is through. A year from now you won’t hear anything about him. He’ll be dead professionally. . . . The public . . .doesn’t like him anymore.” Sinatra was 34 years old.


The story of Frank Sinatra’s comeback in the 1950’s is famous, even fabled: down and out entertainer reads a novel that is about to be made into a movie, finds a character in it that is just right for him, begs for an audition, gets the audition, gets the part, wins an Academy Award, and is welcomed back by a public that admires his pluck and determination in the face of adversity and is ready to forgive all.(In Sinatra’s case, the novel was James Jones’s National Book Award-winning From Here to Eternity, the character was the wisecracking little-guy soldier Maggio, and the award was best supporting actor.) What is less remarked in tellings of this story is the ironic quality of Sinatra’s comeback.

The irony is in the very fact that movies were the vehicle through which Sinatra rose from the depths. To be sure, Sinatra was a gifted dramatic actor and one whom, as the saying goes, the camera loved. (The sound-film camera had the same effect on acting that the microphone had on singing: both encouraged naturalistic expression rather than large voices and big gestures.) Maggio was not the only part Sinatra played skillfully in his 60-film career. Two years after winning his Oscar in 1954, for example, he was nominated as best actor for his portrayal of a heroin addict in The Man With the Golden Arm. During the late 1940’s, he had learned to dance—and well enough so that he did not embarrass himself in numbers with Gene Kelly—for movie musicals like On The Town and Anchors Aweigh. But success made Sinatra a lazy actor—”one-take Sinatra” to his colleagues in the film community, always on time but always in a hurry, as if he were double-parked. To Sinatra, movies were an ephemeral medium—they ran in theatres for a few weeks and then were gone forever. He had grown up before television (much less home videos) came along; the idea that his old movies would be endlessly replayed to a mass audience never sank in with him. The plausibility of Sinatra’s forcefully articulated defense of filming each scene only once—that “the key to good acting on the screen is spontaneity—and that’s something you lose a little with each take”—is undermined when one considers how willing he was to do take after take of the songs he recorded in the studio. “Somewhere in my subconscious,” Sinatra the singer once said, “there’s the constant alarm that rings, telling me what we’re putting on that tape might be around for a lotta, lotta years. Maybe long after we’re gone somebody will put a record on and say. “Jeez, he could have done better than that.”“

In truth, Frank Sinatra was a great actor, perhaps one of the greatest portrayers of characters in situations in history. But he did almost of all his best acting in his singing, and with greater depth in the 1950’s than ever before. Sinatra had always infused his life into his music, inhabiting each song that he sang. But now, having touched bottom, personally and professionally, he had more experience to draw on—he could sing about adult pain, and in a way that men as well as women could identify. Having risen from the ashes, Sinatra also could sing with the confidence, even the swagger of one who has overcome suffering and loss and lived to tell the tale. Finally, years of hard living had changed Sinatra’s voice, in Pete Hamill’s phrase, from “a violin to a viola, . . .with a rich middle register and dark bottom tones.” The area just above middle C became slightly insecure for him, introducing a fragility into his singing of ballads that he was able to evoke for artistic purposes. “He was able to turn a thirty-two bar song into a three-act play,” marveled singer Julius LaRosa.

Sinatra’s talent for acting through his singing was aided dramatically in the 1950’s by the development of the twelve-inch long-playing record, with room for ten or twelve songs instead of just three or four. This technological advance in recording made possible a Sinatra invention that came to be called the “concept album.” Sinatra would begin the planning for each album with a mood or a feeling in mind—despair, perhaps, as in Only the Lonely, or acceptance of loss (In the Wee Small Hours of the Morning), or exhilaration (Songs for Swingin Lovers; A Swingin Affair). He would then choose appropriate instrumentation—heavy on brass for upbeat albums, thick with strings and reeds for sad ones, a string quartet to create an introspective setting, and so on. He would select an appropriate arranger—usually Billy May for raucus up-tempo albums like Come Swing With Me and Come Dance With Me, Gordon Jenkins for mournful albums such as Where Are You? and No One Cares, or (for just about anything) Nelson Riddle, Sinatra’s greatest and most versatile arranger. Finally, Sinatra selected the songs and sequenced them to tell a story. A title song commissioned by Sinatra from Sammy Cahn and Jimmy Van Heusen, for example, opened the No One Cares album. “Why did no one care?” Sinatra asked, explaining the order of the songs that followed. “Because there is a “Cottage for Sale,” that’s why—so it had to be track two. That song’s the saddest ever written—it describes the complete breakup of a home.” Thus, although Sinatra almost never wrote songs, he chose them, grouped and ordered them, and shaped their presentation in such a way that when he sang, it seemed as if the words and music were coming straight out of his mind and heart, even out of his life. Steven Petkof, the coeditor of The Frank Sinatra Reader, is not far from the mark when he suggests that the Sinatra concept albums were the American equivalent of Schubert’s Winterreise, a 24-song cycle based on the despairing poetry of Wilhelm Muller.


Sinatra towered over show business in the 1950’s: 16 record albums (all of them good, and most of them excellent), 23 movies (some of them bad, but almost all of them successful), sold-out concerts in every corner of the globe, and awards of every land. Along the way, he created a “new model for American masculinity,” according to Hamill: the “Tender Tough Guy” whom women loved for his vulnerability and men admired for his swagger and resilience. In movies and on stage, the Sinatra-led Rat Pack—Sammy Davis, Dean Martin, Joey Bishop, and Peter Lawford—offered the mortgage-laden suburban husbands and fathers of the 1950’s an alluring vision of carefree, irresponsible male camaraderie.

What Sinatra lacked—and craved—was respectability. Like his mother, he decided to seek it in the political arena. In 1959 and 1960 Sinatra did everything in his power to help the Kennedy campaign: a partial list of his activities would include organizing and performing at fundraising concerts; recording a theme song (Cahn and Van Heusen’s “High Hopes,” with new lyrics like “K-E-double-N-E-D-Y/Jack’s the nation’s favorite guy”); undertaking, at family patriarch Joseph P. Kennedy’s request, to persuade organized crime leader Sam Giancana to rally Teamsters union support for Kennedy in the crucial West Virginia primary and Illinois general election; canceling a movie he was producing when its writer, a blacklisted member of the Hollywood 10, drew political fire from the right; and (not least) introducing Kennedy to beautiful and available women. In 1968, Sinatra worked almost as hard for Democratic presidential nominee Hubert H. Humphrey.

Sinatra’s hope was that political involvement would cause the public to associate him with statesmen rather than mobsters, with public service rather than hedonism, and with dignity rather than volatility. Instead the opposite occurred. After the 1960 election, as gossip columnists probed Kennedy’s friendship with Sinatra, Robert F. Kennedy and other advisers persuaded the president to cut the singer loose. Invoking the lame excuse of security considerations, Kennedy embarrassed Sinatra by canceling plans to stay at his California home during a western trip in favor of staying with (Republican!) Bing Crosby. Eight years later Humphrey, heeding similar warnings from his own advisers, decided to distance himself from Sinatra after he won the nomination. In both cases, the news media explained Sinatra’s exile by rehearsing every ugly incident, association, and allegation—real or imagined—in their Sinatra files. “It was an old story,” Lawrence Quirk and William Schoel wrote in The Rat Pack. “Politicians always wanted Frank to use his showbiz connections to get entertainers from all across the world to campaign and entertain for them, but once they were in office their advisers would remind them of Frank’s mob ties. In other words, Sinatra had served his purpose, and it was time to give him his walking papers.” As it happens, Sinatra kept walking—right into the welcoming arms of the Republican Party.


Musically, the 1960’s were difficult but creative years for Sinatra. The difficulty was that he was torn between his disdain for rock music (“a rancid aphrodisiac” that was “sung, played, and written for the most part by cretinous goons”) and his desire to remain in touch with young people. This desire manifested itself in a number of ways, including his marriage, at age 50, to the waiflike flower child and actress Mia Farrow, who at 21 was younger than two of Sinatra’s children. It also led him to churn out a number of folk-rock and soft-rock singles. Some of these were marvelous and became a part of his concert repertory for years to come, such as “Summer Wind” and “It Was a Very Good Year.” Others, including “My Way,” he despised but continued to perform because audiences loved them.(He sometimes introduced “Strangers in the Night” at concerts as “one of the worst songs I every sang in my life”—it was also the song that knocked the Beatles’ “Paperback Writer” out of Number 1 on the charts in 1966.) All too many of his intended hits, however, were failures, both musically and commercially. Although Sinatra did an excellent job covering some songs by the Beatles (“Something,” “Yesterday”) and Stevie Wonder (“For Once in My Life,” “You Are the Sunshine of My Life”), his big band version of Simon and Garfunkel’s “Mrs. Robinson” and his disco “Night and Day” were as ghastly in their own way as “Mama Will Bark” had been.

Nonetheless, the desire to innovate that underlay Sinatra’s popular recordings produced bright fruits in other musical areas. In particular, he embraced Brazilian bossa nova—the real thing, not the execrable American version embodied in hit songs like “Blame It on the Bossa Nova” and Elvis Presley’s “Bossa Nova Baby.” Sinatra teamed up with Antonio Carlos Jobim, the young composer of virtually all of the genre’s trademark numbers (“The Girl from Ipanema,” “Quiet Nights of Quiet Stars,” “How Insensitive”) to record 20 songs. His singing on these recordings was unlike anything he had ever done, so soft and delicate as to seem feathery. Sinatra used Claus Ogerman, someone new to him but a Jobim favorite, to arrange the bossa nova albums. Indeed, one of the marks of Sinatra’s 1960’s recordings was the variety of arrangers with whom he worked. In addition to mainstays Riddle, Jenkins, May, and Stordahl, Sinatra did at least one album with Ogerman, Neal Hefti, Sy Oliver, Johnny Mandel, Robert Farnon, Bob Gaudio, and Quincy Jones, and he did several with Don Costa.

Sinatra’s singing also became more jazz-oriented in the 1960’s. His relationship to jazz had always been loosely defined. Sinatra was not a jazz singer in the classic improvisational mode and never had claimed to be. Yet clearly he individualized every song he sang, a hallmark of jazz, and he cited jazz singers as his most powerful musical influences—Louis Armstrong, Sarah Vaughn, Ella Fitzgerald, and especially Billie Holiday and the early Bing Crosby. Jazz musicians, for their part, had always been Sinatra’s strongest admirers. In a poll of 120 musicians by New York Times jazz critic Leonard Feather, Sinatra received 56 votes as the “greatest ever” male vocalist, 43 more than anyone else. Among those who chose Sinatra were Miles Davis, Duke Ellington, Stan Getz, Gerry Mulligan, Oscar Peterson, Billy Taylor, and Carmen McRae.

During the 1960’s, Sinatra recorded four albums with jazz orchestras, three with Count Basic and one with Ellington. In all cases, Sinatra’s vocals were wonderfully and consistently loose and exuberant. But the real joy of these recordings is that he sang as if he were one member of the orchestra. “My Kind of Girl,” for example, a song from the 1963 Sinatra-Basie album, begins intimately with Sinatra and jazz trio, as if he were telling a small group of friends about the new girl he had met. The Basie band then enters in full force, and Sinatra responds by adding swagger and volume to his singing—he has a bigger crowd to talk with now. Then the flutist has his say—for two minutes—before the singer returns to wrap things up. In this song and in others on the Basie and Ellington albums, Sinatra is clearly feeding off the energy and spontaneity of the jazz musicians who accompanied him. Yet the influence seems mutual. One of the things Sinatra seems to have persuaded the instrumental soloists to do was to consider the lyrics of each song in their playing of it.


Despite his musical innovations of the 1960’s, Sinatra felt creatively stymied by the dearth of new songs he thought were worth singing. “There’s a lot of garbage out there,” he complained. “Nobody’s writing any songs for me and I don’t know what to do about it.” On June 13, 1971, six months shy of his 56th birthday, Sinatra announced that he was retiring from show business.

Retirement lasted only 29 months, and even then it was not unbroken: Sinatra sang at the White House when the Italian prime minister visited President Richard Nixon in April 1973. Democratic presidents never had invited Sinatra to the White House on state occasions; Republican presidents, especially Nixon and Ronald Reagan, did so all the time. For Sinatra, this was reason enough to become a Republican. He was, in the writer Gay Talese’s wonderful phrase, “Il Padrone,” a man of “fierce fidelity. . . . This is the Sicilian in Sinatra: he permits his friends, if they wish to remain that, no easy Anglo-Saxon outs. But if they remain loyal, then there is nothing that Sinatra will not do in turn—fabulous gifts, personal kindnesses, encouragement when they’re down, adulation when they’re up.” Spiro Agnew, who resigned as vice president in October 1973 in order to avoid imprisonment on bribery charges, was a special friend and beneficiary of Sinatra’s generosity, never more so than when he hit rock bottom.

When Sinatra did come out of retirement later in 1973 (this time as “Ol’ Blue Eyes”), it was to a different career. The screen actor who had averaged two movies per year in the 1950’s and 1960’s essentially stopped making films. He recorded less frequently and, although he occasionally found a new song that he could do something with (especially Stephen Sondheim’s “Send in the Clowns” and Kander and Ebb’s “Theme from New York, New York”), much of his best work consisted of new versions of old standards: volume 1 (“The Past”) of Trilogy with Billy May; She Shot Me Down, a collection of saloon songs arranged by Gordon Jenkins; and L.A. Is My Lady, a jazzy album with Quincy Jones that featured a rip-roaring version of “Mac the Knife.” Because Sinatra’s singing relied so much on phrasing—rhythm, dynamics, and diction, all in the service of interpretation—the coarsening of his voice as he got older was less damaging to his art than would have been the case for most singers. In ballads, he exploited his vocal cracks and crevices to artistic effect. As Rolling Stone music critic Mikal Gilmore wrote, “Sinatra knows enough to surrender to old age, to sing his songs in the voice of an old man stripped of most hopes and all conceits.”

Prior to his retirement, Sinatra had spent most of his days on movie sets and in recording studios; when he performed live, it was usually to casino audiences in nearby Las Vegas. Now, with time to spare, he took to the road. From 1974 to 1995, when at age 79 he gave his last concert, Sinatra sang in one part of the world or another nearly one hundred nights each year. Borrowing from rock stars, he did most of these concerts in stadiums. For a while, Sinatra’s 1980 concert at a soccer stadium in Sao Paolo, Brazil, held the record for the largest live audience in recorded history: 175,000.

Perhaps the most astonishing event of Sinatra’s final years was the release of the two Duets albums in 1994 and 1995. Duets paired Sinatra with contemporary singers such as Bono, Aretha Franklin, Luther Vandross, Carly Simon, Linda Ronstadt, Stevie Wonder, Patti Labelle, and Chrissie Hynde, all of whom joined him to sing standards from his 60-year songbook. Duets “shipped platinum” (that is, it sold more than one million copies before being released) and reached the top of the charts, elbowing aside grunge and other rock bands like Pearl Jam and Nirvana. Most significant, as the New York Times music critic Stephen Holden wrote, Duets was “a symbolic healing of the generation gap in pop taste, a final, reconciliatory swan song.”


What a long-distance race the lonely singer ran. In the 1940’s Sinatra was “The Voice,” married to Nancy, his sound a violin, his fans teenage girls. In the 1950’s and 1960’s, the new viola-voiced Sinatra, after shaking off Ava and marrying the young actress Mia Farrow, became “The Chairman of the Board,” presiding over an adult audience dense with men as well as women. In the 1970’s and afterward, married to the former Barbara Marx, he became “Ol’ Blue Eyes,” his voice a cello headed south to a bass. A line in an early Sinatra song, a glorious flagwaver about racial and religious tolerance called “The House I Live In,” went: “and a dream that’s been a growing/for a hundred and fifty years.” Toward the end, when Sinatra performed the line read: “for more than two hundred years.”

I learned about Sinatra’s death in a strangely marvelous way. I was walking through the campus of the college where I teach on the eve of graduation for the Class of 1998, which happened to be May 14. Unsurprisingly, music blasted from the windows of the senior dormitories; astonishingly, much of it was Sinatra music. “Have the grandparents taken over the dorms?” I asked a student jokingly. He told me that Frank Sinatra had died. Feeling a complexity of emotions worthy of a Sinatra song (“Glad to Be Unhappy”?), I teared up—sad at the singer’s death, thrilled at his apparent immortality.

The next morning I got another surprise. In a typically lame effort to impress my teenage son, I showed him what rock musicians like Tom Petty and Bono had told the paper about Sinatra’s influence on them and their music. Sex, attitude, swagger, danger—everything that made rock what it was, they said, could be traced to Sinatra. “Of course, Dad,” said my son. “All the rockers like Frank.” His tone let me know that even if Sinatra had become cool, I was as far behind the curve as ever. I didn’t mind a bit.


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