Geeks of America, Hail Your King The late-night lothario in action

Conan O'Brien, he of the russet pompadour and blancmange complexion, likes to joke about how white he is. Sometimes he's referring to his actual lack of skin pigment, but it's more often a figurative admission of uncoolness. While his curriculum vitae might be stellar, O'Brien is painfully deficient in the street-cred department.

For one thing, he's the Harvard-educated son of a lawyer and a research physician. (Children of privilege are inherently dorky; brainy ones even more so.) For another thing, he's the gawkiest Bostonian since Larry Bird. And long before Ashlee Simpson's wince-inducing Saturday Night Live hoedown, O'Brien was known for punctuating awkward moments with an impromptu jig. Yeah, it's safe to say that Conan is an unabashed geekburger. He might growl coyly at supermodels, but he's never been caught dating one.

And yet, Conan's willingness to play the clown prince of Losertown (population: countless) has been the unlikely secret of his success. From the very first season of Late Night with Conan O'Brien, the gags have paraded society's 90-pound weaklings. Remember the Wussy Wagon, an oversized Radio Flyer full of sniveling businessmen? Seemed absurdist at the time, though it's hard not to see it today as a commentary on white-collar cowardice.

O'Brien's sidekick for the first seven years, the dearly missed Andy Richter, was a tubby deadpan foil to Conan's neurotic. Richter often appeared shirtless in sketches, and the sight of his exposed bosom evoked painful memories of the kids who got picked last in gym class. Meanwhile, Andy's "sister" (played by SNL darling Amy Poehler) often showed up to profess her unrequited love for Conan, causing all parties involved to cringe. One popular sketch, "Bulletproof Legs," featured cast member Brian McCann bragging about his impenetrable legs, then taking a bullet to the chest. The humor was deliciously dark; no matter how hard these guys tried to catch a break, they always wound up vulnerable.

After Richter left the show in pursuit of superior projects (like Quintuplets?) O'Brien seemed even more exposed. Sure, he still had jaunty bandleader Max Weinberg at his side (and oddball announcer Joel Godard declaring his love for Asian male prostitutes), but the formula had permanently changed. As the seasons marched on, Conan matured, married, and sired a kid with an appropriately obscure Irish name. Perhaps this peculiar rite of broadcast puberty is what compelled NBC to recently name O'Brien as the heir to the Tonight Show, effective upon Jay Leno's retirement in 2009.

Perhaps the decision was predictable, but it seems incongruous that in four years, the man famous for crafting sharp collegiate in-jokes will court America's favor on Carson's legendary soundstage. I suppose the Masturbating Bear is no less dignified than some former Tonight Show fixtures (Dom DeLuise, anyone?). But is the show's current middlebrow fan base really going to warm to an Ivy League kid with a yen for surrealist comedy? It's hard to imagine Leno interacting with "Coked-Up Werewolf," "Gaseous Weiner," or any other members of O'Brien's stable of characters.

O'Brien may no longer be the hapless also-ran of late night, but he still seems fascinated by geek culture, public humiliation, and outsiders burdened by brilliance. After the Grammy telecast, he taunted the unknown gearheads who won the technical awards, then encouraged them to trash John Mayer's hotel room. He recently appeared at Las Vegas's Consumer Electronics Show alongside übergeek Bill Gates, pimping Microsoft's latest products. And Late Night's most feared and beloved character, Triumph the Insult Comic Dog, mocks Star Wars superfans and sci-fi enthusiasts in a way that suggests he's running with his own pack. O'Brien might gleefully point a finger at his nerd brethren, but he's self-aware enough to realize there are three fingers pointing back at his freckled visage.

O'Brien, now 41, can only milk the boyish angle for so long before funny-pathetic becomes pathetic-pathetic. He and Andy Richter used to don silver capes and fantasize about "The Year 2000" to humorous effect. It's time for O'Brien to begin formulating a plan for 2009. By then, his self-conscious comedy (and that carrot-colored pomp) might be growing thin.

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