Conan O'Brien is way more cool than most of us, but still manages to be the pasty poster-boy for nerds everywhere.
For one thing, a relatively unknown writer, with no experience appearing on television wound up replacing comedy legend and talk show host David Letterman, almost without knowing he got the job. When was the last time someone asked for you to host a comedy show while you were eating a hogie? At age thirty (a time that some of you are still living with your parents) he was wearing jeans with a sport coat, on television.
In addition to being the only man that can be credited with replacing more than one living legend, he shows a surprising ability to make fun of himself and seem genuinely humble. From the first time he appeared on stage as himself (The Tonight Show with Jay Leno circa 1992) he still seems uncomfortable receiving applause and pleads with the audience to "tone it down" in order to satiate his ego. This is in an industry where people are still doing anything they can to get applause.
This is a man who is not afraid of criticism. Before filming the first episode of "The Tonight Show" Conan held a focus group with the older set to see how he'd fare in his new time slot with the geriatric crowd. Lots of producers and directors do this, but O'Brien wanted to be present for the taping; so instead of having an industry professional hold the group and report the findings, he had an Academy Award winning make-up artist turn him into a completely different person,
kept a straight face while bad-mouthing himself and listening to the un-aware focus participants give him their real opinions about him. That takes a pair, even if you can't beat up the champ!
In another all out Balls move, Conan had the Audacity to bring on Paris Hilton with a Golf club, compare her to Bob Hope, and have her perform one-liners in a self-depreciating style that basically turned her into a caricature of herself. Also, friend and sometimes guest on the show, Larry King is a good humored butt of many of his jokes, including an impression that involves his suspenders, constantly spiking how old he is and even cutting segments of his show to appear stranger than they are. In addition to this fearless attitude torward satire he also throws in an almost endless level of jokes designed either to scare off potential guests, or see if guests even watch the show. The night before G.I.Joe star Sienna Miller was slated to air, they spiked the film in a segment where he and Andy Richter (O'Brien's long time side-kick) make snide comments about films. Needless to say, they were not all that nice. Sienna still came on the program, and nothing was mentioned. Balls. Huge ones. Made of white chocolate and bacon.