The Singer

Frank Sinatra has received far too many tributes already. Even before his death last month there was the 80th-birthday hoopla of 2 1/2 years ago, followed by the flock of recently published books circling, vulture-like, in clear anticipation of his passing. At this point any recounting of his accomplishments--his unassailable greatness as a singer, his somewhat more assailable greatness as an actor, his impeccable taste as a curator of the great American songbook, his ancillary talents as both philanthropist and thug, his status as a totem of midcentury masculinity--inevitably takes on a dutiful, ritualistic air. So what better way to breathe a little life into the process than with an insult?

"George Steinbrenner with a voice" was the epithet coined by a colleague of mine--born in the baby boom's dead center, it should be noted--who objects to the bad-hair Republican bluster of Sinatra's later years, his belting out of all those anthems of middle-aged self-assertion. He did it his way. He can make it anywhere. He picks himself up and gets back in the race--that's life, or Sinatra's blowhard version of it anyway. It is the artfully projected world view of a casino entertainer, a glorified greeter, whose job it was to make old guys with bum tickers and second wives feel good about themselves.

On one hand, my colleague's view of Sinatra as scourge of baby boomers--the anti-Judy Collins, if you will--is a crude caricature of a complex artist, as reductive as any neo-swinger's fetishistic prattling about the man's way with a pocket handkerchief. On the other hand, it is a caricature I too used to believe in.

Should anyone even care what people like my colleague and me think of Sinatra? My own higher notions about music were incubated while listening to Jethro Tull albums (whoa--a flute!). Sinatra's body of work, meanwhile, stretches back to the 1930s and is nothing less than "the final statement on pre-rock pop," as Will Friedwald, the invaluable Sinatra scholar, recently wrote of the Songs for Swingin' Lovers! album, released in 1956 and generally considered Sinatra's finest LP. "Something radically different just had to come next," Friedwald continues, "because nothing in the realm of Tin Pan Alley could top this bravura celebration of grown-up love." You can't sum up Sinatra's achievement more succinctly than that.

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