He loved, he brawled, he had style, he had guts, he could even act. And, oh yeah, he defined American pop

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But he had nearly 40 years of performing left ahead of him in 1956; more than two-thirds of his professional life was spent in the rock era, much of it reacting to rhythms and attitudes he found alien. "The most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear," Sinatra wrote of rock 'n' roll at the time of Elvis Presley's pre-eminence, no doubt hoping to turn back the Mongols. It didn't quite work, and in efforts to maintain his commercial viability, Sinatra would eventually record Presley's hit Love Me Tender as well as works by Paul Simon (Mrs. Robinson), George Harrison (Something) and Joni Mitchell (Both Sides Now). The results were often awkward--this is the Sinatra people like me used to make fun of. But listen with more knowing ears: when Sinatra sings "You stick around, Jack, it might show" on Something, you get the feeling not that he's hoking it up Vegas-style so much as he's rooting around for rhythmic complexity in a beautiful if simple song; he's a muscle car idling on a leafy suburban cul-de-sac.

Sinatra--this is both his gift and, on occasion, his downfall--is always Sinatra. Beyond his technical prowess as a jazz-influenced pop singer, building on the innovations of Louis Armstrong, Bing Crosby and Billie Holiday, there is the sheer force of conviction, feeling, the weight of personal history in his voice. In this, only Holiday is his rival--perhaps even his better. Both exemplify what people in my generation like to flatter ourselves is unique to rock 'n' roll and its offshoots: the immediacy, the idiosyncrasy, the genuineness of expression. Sinatra is the century's musical equipoise, the pivot between the carefully crafted pop of its beginning and the looser, fiercer sounds of its end.

These are not original observations; people who had the fortune to grow up with Sinatra already knew. I first caught on when, while listening to a Sinatra greatest-hits album I had bought for a girlfriend as an ironic courtship gesture--I was young, it was the '80s--the song Strangers in the Night caught my ear. It's an admittedly queer place to start amid the glories of the Sinatra canon, a chintzy little hit from 1966 with a dopey pop-rock arrangement; the singer himself gives it the brush-off with his famous dooby-dooby-doo coda during the fade-out. But not everyone can start with What Is This Thing Called Love?, and even here Sinatra manages to invest the ticky-tacky lyrics--"Strangers in the night/ Exchanging glances/ Wondering in the night/ What were the chances"--with a palpable yearning that transcends, maybe even exalts its surroundings. I was hooked.

This, really, is my point: masterpieces--like Songs for Swingin' Lovers!--are easy to love. They are what we remember artists for, but they aren't always as illuminating, or as cherishable, as the failures and throwaways. More often than not, even Sinatra's crud speaks his virtues. You can't ask much more of a performer than that.

Bruce Handy writes TIME's Spectator column. He thought he'd be sick of Sinatra by now

Sinatra championed their work. They gave his voice something to soar on HAROLD ARLEN His best-known song may be Over the Rainbow, but more typical are tunes like Stormy Weather, infused with blues shadings. His One for My Baby (lyrics by Johnny Mercer) gave Sinatra a trademark, the daddy of all saloon songs THE GERSHWINS Brothers George (music) and Ira (lyrics) brought the rhythms and harmonies of jazz to Broadway, the concert hall and the opera. Sinatra used their A Foggy Day to announce the harder-swinging style of his LPs in the '50s and '60s COLE PORTER A debonair Yalie, Porter wrote complex melodies with witty, sometimes jaundiced lyrics that (in tandem with Nelson Riddle's arrangements) inspired Sinatra's greatest performances, including I've Got You Under My Skin
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