His Second Act

Editor’s Choice: How Frank Sinatra staged the most spectacular comeback in American cultural history

Frank Sinatra, the greatest vocalist in the history of American music, elevated popular song to an art. He was a dominant power in the entertainment industries—radio, records, movies, gambling—and a symbol of the Mafia’s reach into American public life. More profoundly than any figure excepting perhaps Elvis Presley, Sinatra changed the style and popular culture of the American Century.

FRANK SINATRA creating the Great American Songbook

Frank Sinatra: The Man, the Music, the Legend, a long-awaited collection of essays gathered from a famed 1998 conference at Hofstra University and edited by Jeanne Fuchs and Ruth Prigozy, probes various aspects of Sinatra’s influence in his long career (he was a national figure from 1939 until his death, in 1998). But it insists, both explicitly and in its editors’ selection of subjects and themes, that the “proper historical setting” for its subject “is the fifties.”

Although that point can be debated, the 1950s—more precisely, the period from 1953 to the mid-1960s—was clearly the era of Sinatra’s supreme artistic achievement and deepest cultural sway. It amounted to the most spectacular second act in American cultural history. In the early 1940s, following his break with the Tommy Dorsey band, Sinatra had emerged, thanks largely to swooning bobby-soxers, as pop music’s biggest star and a hugely popular Hollywood actor. By the end of the decade, he was all but washed up, having lost his audience owing to shifting musical tastes and to disenchantment over his reported ties to the Mob, and over his divorce, which followed a widely publicized affair with Ava Gardner, whom he married in 1951. He soon lost his voice (he would never fully recover his consistently accurate intonation and precise pitch), his movie contract with MGM, his record contract with Columbia, and Gardner—their passionate, mutually corrosive entanglement plainly and permanently warped him. But in 1953, his harrowing, Oscar-winning performance as the feisty, doomed Maggio in From Here to Eternity made him a star again.

More important, in that year he also signed with the trendsetting, L.A.-based Capitol Records, a move that afforded him his greatest role: his own musical and stylistic reinvention. The 16 concept albums that followed, his most remarkable achievement and among America’s enduring cultural treasures, defied public taste and redirected it toward what would be known as the Great American Songbook. With his key collaborator, the arranger Nelson Riddle, Sinatra jettisoned the yearning, sweet-voiced crooning of his Columbia years in favor of a richer voice, greater rhythmic invention, and more knowing and conversational phrasing. He had always said that Billie Holiday was his most profound musical influence, and at Capitol, accompanied by Harry Edison, the former trumpeter for Count Basie, he was even more deeply open to jazz influence, as he invested up-tempo songs (which he had rarely performed at Columbia) with a tough, assured swing. For their part, jazz musicians overwhelmingly selected him “the greatest-ever male vocalist” in a 1956 poll, and Lester Young and Miles Davis—never partial to white musicians—ardently praised him.

And now, apparently because of his tortured relationship with Gardner, Sinatra burned off all remaining affectations and sentimentality and sang his ballads with bitterness, directness, and masculine vulnerability (“Ava taught him how to sing a torch song,” Riddle said). A midcentury artist with an admitted “overacute capacity for sadness as well as elation,” Sinatra invested those largely decades-old ballads with a modern anxiety and ambivalence. In his album sequences and in such swinging songs as “Night and Day,” “Day In, Day Out,” “Old Devil Moon,” and especially his greatest recording, the 1956 “I’ve Got You Under My Skin,” he juxtaposed bravado and panic, ecstasy and uncertainty.

With this new sensibility, which Pete Hamill has aptly termed the “Tender Tough Guy,” Sinatra created—as several of the pieces in this collection illuminate—the most important model of masculinity for a generation of Americans. He had transformed his persona from that of a skinny, boyish, even androgynous heartthrob with Brylcreemed curls, too-big jackets, sailor suits (!), and floppy bow ties into that of a suave man of authority and sensitivity in crisp, slim-line suits. He appealed not to teenage girls but to their mothers and fathers. The jazz critic Gary Giddins, one of the most astute writers on the singer, summed up the transformed Sinatra: “Above all, he was adult. He sang to adults.”

In so doing, Sinatra held at bay the cultural changes that had helped bring about his earlier downfall. He came of age musically in a peculiar period: the only era in which jazz, as played by the big bands, was the most popular musical form. Since the 1940s, he had been recognized as the leader of a movement to establish the music of such composers as Cole Porter, Irving Berlin, Rodgers and Hart, and Jerome Kern as an art form, but postwar audiences turned away from Sinatra primarily because they no longer wanted to hear the music he wanted to sing. Ironically, his decision to embark on a solo musical career hastened the demise of the big bands and unmoored a mass audience from sophisticated popular music. While urbane songs would have appealed to audiences who danced to Benny Goodman and Artie Shaw, until Sinatra altered popular taste, the postwar soloists—even such savvy chanteuses as Peggy Lee and Rosemary Clooney—made their fortunes and kept their contracts by recording novelty songs. Sinatra saw this firsthand, when Columbia enjoined him to record the godawful “Mama Will Bark,” with the busty comedienne Dagmar (it’s as bad as you imagine—complete with simulated barking).

On his hugely popular and artistically glorious Capitol albums, Sinatra expanded and enlivened the repertory of standard American songs (astonishingly, before his recording of it, “I’ve Got You Under My Skin” hadn’t been a significant entry in the Porter catalog) and became its most commanding interpreter. With his clear, relaxed enunciation and sublime phrasing, he also codified the sound and rhythm of casually elegant spoken American English. The seamlessness, ingenuity, and rightness of that phrasing is readily apparent when you try to sing along with him and still can’t foretell his stresses and caesuras in a recording you may have heard a hundred times. (David Finck and Samuel L. Chell dissect Sinatra’s vocal artistry in two succinct and exceptionally precise pieces in this collection.)

Nonetheless, Sinatra’s musical achievement—which constituted perhaps the last sustained occasion when elite and mass musical taste would coalesce—was really only a prolonged holding action made possible by his preternatural talent and charisma. As Will Friedwald, the most thorough analyst of Sinatra’s musicianship, wrote, Sinatra was, for all his popular appeal, “completely out of touch with American culture as it evolved from [the late 1940s] onwards.” Friedwald—no surprise—excoriates popular culture, not Sinatra, for this. But whether or not you agree, the fact that, as Giddins points out, Sinatra’s artistic maturity coincided with the peak of Elvis’s appeal shows the extent to which Sinatra’s imperishable accomplishment was a cultural outlier. And though Sinatra’s second act clearly represented the justifiably bemoaned final triumph of grown-up pop-cultural taste, Sinatra himself helped hasten the inevitable triumph of youth culture. His musical persona may have been “adult,” but he insisted on merging that with his public face, which was too often anything but. You could hardly blame the kids for rejecting him.

To be sure, Sinatra, an exquisitely complicated man, was doggedly committed to racial equality long before it was a fashionable cause. He was also a consistently generous artist and capable of astonishing grace and thoughtfulness. But—aside from consorting with killers; procuring for the doped-up, mobbed-up, and coarsely exploitative JFK (if anything, Camelot sullied Sinatra, not the other way around); and regularly displaying a potentially murderous temper—he perversely made sure that his ardent listeners grasped that his juvenile, vulgar, and increasingly pathetic Rat Pack antics couldn’t be reconciled with his carefully wrought musical reinvention. This was made clear on his 1966 album Sinatra at the Sands, which contains both his lovely and swinging renditions of “Angel Eyes” and “Luck Be a Lady,” accompanied by the Count Basie Orchestra, and his notoriously cringe-inducing monologue that combined yucky corniness and mean-spiritedness. If this was mature urbanity, who needed it?

Sinatra gave Sammy Davis Jr. his career, and his fiercely loyal, public embrace of Davis, often in the teeth of bigotry, was principled and heroic. But in their Rat Pack shows, he made Davis the butt of race-oriented jokes, and Davis knew a Sinatra both vindictive and considerate, both scummy and courtly. Photo by Sammy Davis, Jr. assembles beautiful and revealing snaps that this gifted amateur took in the 1950s and ’60s of the Hollywood elite at play (including a sad and sweet image of a little-black-dressed Marilyn tucking a small boy into bed as a late-night party hums in the other room), of Vegas showgirls, of politicians and mobsters, of Martin Luther King Jr. And of course there is Sinatra, in all his dangerous glamour—joshing with Shirley MacLaine and the rest of his band of nocturnal carousers, brooding, on the phone in sharply tailored pajamas (no doubt after sleeping through a good chunk of the day). Speaking of that glamour, Davis said, “Only two guys are left who are not the boy next door: Cary Grant and Frank Sinatra.”