Late Night With Conan O'Brien

Recently, I stumbled upon an old Howard Stern E!-channel rerun in which the King of All Media was giving the Prince of Pale Irish-Catholic Boys a hard time about the then-piddly ratings for Late Night With Conan O’Brien. It must have been a year or so into his stewardship of what had been David Letterman’s old time period, and fear still flickered in O’Brien’s eyes.

Wearing a leather jacket like a suit of hipster armor to protect him from Stern’s gleeful predictions of imminent cancellation, Conan was plucky, game, and perhaps a little weary, even hurt. You could read it in his face: ”Is this never going to end? Am I always going to be the new kid who has to prove himself?” He parried Stern’s verbal thrusts with the smart-alecky wit that had already seen him through the harrowing gauntlet of writing for The Simpsons, but at that point, you had to look at this obviously intelligent, shrewd, ambitious young lad and think: This geek’s a goner.

Well, here he is, almost five years on, and Conan O’Brien has proven to be more than a survivor — he’s the cool cat the college kitties love, the late-night host with the freshest approach to his genre. The callow freckle face now seems like a natural, and on Sept. 15, he’ll bring his lanky frame, his crimson pompadour, and his kicky sidekick, Andy Richter, into prime time for a fifth-anniversary special on NBC.

To be sure, some of this is due to the nature of television: Stay on the small screen long enough and the public automatically starts treating you like a bona fide star — doesn’t matter whether you’re Mary Tyler Moore, the host of a cable-access stamp-collecting show, or Dennis Miller. True, O’Brien’s audience is still only 40 percent of lead-in Jay Leno’s. But in the court of media opinion and by the verdict of a jury of his viewing peers, Conan is the Man. He attracts the right demographic with the max mix of the moment: good taste in musical acts (where else can you see Pulp or Jonathan Richman?) and intentionally bad taste in comedy material (Conan’s Monica Lewinsky jokes, especially those he does with Robert Smigel’s Clinton photo with the moving lips, are scathing, and all the more brutal for being so cheerfully delivered).

Me, I still like Letterman best, but that’s because at this point in my life, I appreciate middle-age craziness more than young-adult looniness (”Paul, on the inside, I’m a bubbling cauldron of problems,” Dave confessed to his bandleader recently, and so help me, there was something like pride glistening in the old man’s bespectacled eyes). O’Brien’s Late Night, however, is aging well indeed. His sketches may be wildly uneven, but his opening monologue is quick and snappy; his interviews have become relaxed, chatty, and playful. And, rare among his peers, he’s particularly good — neither rattled nor hokily flirty — with women, whether it’s historian Doris Kearns Goodwin or Sex and the City giggler Sarah Jessica Parker. (Come to think of it, maybe he’s just good with women who have three names. Can’t wait for that Joyce Carol Oates booking.)

My fellow TV critics are already making whiny noises about how Craig Kilborn is going to bite into O’Brien’s Slim Jim ratings when the Daily Show star replaces Tom Snyder opposite Conan on CBS in January. But while Kilborn and O’Brien share youth and a willingness to go for the jugular, Conan has it all over the often-snide, chilly Kilby in the area of on-camera affability, a crucial quality in sustaining a talk show over the long haul.

Fielding questions at a TV-critics press gathering in July, O’Brien noted: ”I’m not a slick professional. I’m this person who got in over his head and just stuck to it.” Slick-free perseverance is rare on TV and something to be treasured. But it doesn’t look as if O’Brien’s increasing professionalism is making him any less rascally. A recent sketch had him decking a nun — proof, I thought, that our Conan will always be a good, neurotic Irish-Catholic boy at heart. A-