Then Madonna took the stage, thank God, to introduce the evening's surprise guest. She called him a talent the likes of which surfaces but a handful of times in a century. Seconds later, when Paul McCartney strutted forward, I was struck by his quiet self-assurance, his apparently secure knowledge that he was all those things the Material Girl had called him. His unimpressed aplomb contrasted neatly with all the young dudes who were so desperate to attract attention. Here at last was a cool white guy.

Ever since Marlon Brando and James Dean taught white men the devil-may-care aspect of cool, when such an attitude was the province of the young, Hollywood and rock 'n' roll have done the proselytizing. Everyone -- or at least those of us with enough time on our hands to care -- can trace their own lineage, and the list is potentially long. But there have been a handful of icons who, through artistry or artfulness, elevated cool to the point of regality -- guys like Brando and Dean, Frank Sinatra, Warren Beatty and, of course, Elvis Presley and countless other musicians from a time when "cool rock star" would have been considered a tautology.

The striking thing about them all is that they achieved a kind of princely dominance by the time they were in their 20s and, importantly, they wore it well. Dean was killed in a car crash at 24; The Voice had his first number one single, "I'll Never Smile Again," at age 25; the presidentially coy Beatty was 24 when he found "Splendor in the Grass" with Natalie Wood; Elvis had them swooning at 20. And now? Thanks to the current demographic appeal of pre-fab teen movies and sanitized pop music, we are being haunted by the ghosts of New Edition and the Brat Pack.

Is there an entertainment industry-wide problem here? Of course not, if you take a financial viewpoint -- the entertainment industry does just fine, thank you. Maybe its finely honed strategy of product positioning leaves little room for iconoclasm. The market's tastes form a bell-curve, and cool anti-heroes have their place -- off to the side of that big bulge in the middle where the innocuous cluster together, where you find the Backstreet Boys, or Garth Brooks, who only pretends to be cool by posing as a rocker. Our oft-lamented media saturation makes celebrities into commodities with the built-in obsolescence of a consumer appliance, but with shelf-lives a fraction as long as, say, a Sony Trinitron.

But what about aesthetics? If you use media prominence as a measuring stick (the discussion is, after all, about icons), it doesn't matter where you look -- television, movies or music -- we are in short supply of young white artists who possess the kind of lasting qualities we attach to the idea of "cool." This has happened before, especially in the cyclical music business, which has produced countless other eras of teeny-bop pop. But many earlier teen idols, the best of whom matured emotionally and artistically -- Sinatra and the Beatles, for example -- only got cooler as they grew up. It's hard to envision the same kind of creative flowering for N'Sync, the boy group that has performed Christopher Cross' "Sailing" in falsetto while suspended like circus acrobats over the audience.

Times like these serve to remind us that cool is a white man's idea of something more purely black, like early rock music. Miles Davis oozed cool. James Brown has it in his bones. Unsurprisingly, then, plenty of hip-hop stars, male and female, exude cool. But what about Lenny Kravitz? He derived his once-cool persona from the same people he mimicked with his music -- Jimi and Jimmy, among others. Kravitz's near-simultaneous release of the song "Fly Away" as a single and in a car commercial -- two videos for the price of one (and tidy revenues on the other) -- was crass enough to lose him what little credibility he might have once possessed.

Older generations of stars have been similarly losing their cool, refuting the idea that the quality might endure mostly as a generational hallmark. Thanks to the endless promotion and recycling of celebrities like Mick Jagger, we see cool can be squandered through overexposure, even by legends. The Rolling Stones and just about all the other great old rockers -- even Lou Reed and Bob Dylan -- have also licensed songs to commercials. "Sellout," once the antithesis of cool, is now just another word for nothing left to lose.

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