Sometimes Kilborn's frat-boy irreverence went bad, like when he made a degrading remark about Daily Show co-creator Lizz Winstead that got him suspended for several shows.
But hat was a mere speed bump, and soon Kilborn was recruited to replace Tom Snyder as the follow-up to the Late Show with David Letterman.
Snyder had held the post-Letterman slot for several years. He is a legend in the late night talk show world for his intimate interview style and audience-less studio.
Snyder's home audience skewed older though, and CBS wanted a fresher face more attunded to short attention spans.
Craig fit the bill, and his show is a doozy.
The set is made up like a midwesterner's fantasy of what a Hollywood Hills bachelor pad looks like.
The seats are plush and leather. There's no house band, and Kilborn introduces himself and his guests at the beginning of every show.
The guests typically fall into three categories: Maxim-magazine quality model/actresses, young male actors and older legends of comedy.
The setting is intimate. It's Craig and guest face to face, and although it's probably all been rehearsed, it doesn't have the canned feel of Leno, et.al., where a typical conversation goes like this.
Host (to guest): So I hear you have a pet llama.
(audience applauds)
Guest (feigns surprise): How did you know that? I don't know what to say.
(Flollowed by a five-minute funny story).
This sort of format, which Letterman, Leno and O'Brien follow, is based on old vaudeville theater or early live television.
The idea is for the show to run like a well-oiled machine. Spontaneity is discouraged, and the humor suffers for it.
The Late Late Show with Craig Kilborn show is different.
Rather than vaudeville, the Kilborn show seems influenced by basketball. In basketball, preparation for game time is essential, but after tip-off new situtations reveal themselves, and the game requires a mastery of organized chaos.
Kilborn plays it off the cuff. He's not afraid to make a Stuff model feel awkward by suggesting that she's not paid for her talent.
It's the Kilborn show, and he's not about to help a limping guest through a segment. He expects the personalities that grab a chair on his airtime to bring their game face.
To come to play.
And if not, they deserve to look a little foolish.
During the fall and early winter of 2001, when this country and its sense of humor seemed caught in a flux, the Kilborn show floundered a little too.
During his Daily Show days, he'd made an offensive joke about the 1993 World Trade Center attack that now seemed very, very unfunny.
Whenever a guest alluded to the attacks, Kilborn twitched and not just a little. Maybe he felt guilty, maybe he was out of his depth, no Ted Koppel he.
So as winter turned to spring, and everyone's mood improved, so too did the Kilborn show, as it regained its vibe of triviality.
Because unlike the other self-apologists who occupy late night television, Kilborn seems to enjoy hair gel.
And he should. It agrees with him. He wears it well and guiltlessly. And it's his embrace and critique of falseness that makes Kilborn's show the funniest and most lively in late night.
The Late Late Show with Craig Kilborn airs at midnight from Monday through Friday on CBS.
