“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.