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.
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