In general, I like Conan O'Brien and his self-deprecating humor. And I like his Clueless Gamer segments, where he—and often a celebrity guest—play a new game, riffing around in a sketch and often playing terribly. They're gently funny instead of uproarious, but that's kind of the schtick. It's entertaining, if not exactly overstimulating, YouTube fare.
But the most recent episode on YouTube, featuring supermodel Kate Upton and the gorgeous-looking upcoming side-scrolling action game, Cuphead, got creepy. While Upton is pretty clearly in on the joke, Conan awkwardly hits on her, inviting her to a romantic dinner that he keeps claiming he does with "all his guests," encourages her to get drunk on champagne, and eventually makes her play the co-op game with him on one controller, so that their bodies touch.
Again, this is obviously scripted, and Upton is pretty clearly in on the joke, blithely refusing is advances and talking about her fiancee. But it just reads, frankly, a little gross—especially the ending assertion where Conan yells about her thinking he's an "asexual freak," which, c'mon dude. That's a slur in place of a punchline.
As much as Conan is supposed to be the butt of the joke here, it's pretty hard not to identify with the woman who is defending herself against obviously unwanted advances. On his TV show, where he, pretty obviously, holds all the power. She pretty much has to play it cool and go with the joke.
Other recent episodes are funny without being shitty or encroaching on a woman's space and making advances towards her. The Will Arnett Arms episode has the two comedy bros throwing punches and doofy burns at one another. Last month, his review of Injustice: Gods Among Us was fun and cute.
O'Brien usually plays up his image as a sort of sweet, self-deprecating buffoon. His persona is fun and likeable. And, of course, there's nothing wrong with finding Kate Upton attractive. But it would've been so easy to play this sketch without that creep factor.
I think you can do better, Conan.