Conan O’Brian Gets Creepy With Kate Upton Over ‘Cuphead’

The Clueless Gamer segment was awkward instead of hilarious.

This is a companion discussion topic for the original entry at

Yeah, I typically enjoy Clueless Gamer for what it is, light-hearted fun with Conan not understanding video games, and they’re generally well edited and entertaining.

This last episode was not, and it encapsulates what I dislike about Conan, or rather, his character on the show. In other unrelated segments he’s gotten overly flirtatious with more or less any pretty women, and it creeps me out more than it entertains me.

Beyond creeping on Kate, there wasn’t any goofs on the game either, just one bit from start to end :I


Isn’t it funny when gamer guys creep on women because they have no social skills?

Sometimes I wonder if the writers for these segments also have the same paralyzing inability to really grasp others when they write this stuff, especially because gamers are not the only demographic who do this stuff.


Yeah, I mean, I’ve never really been a fan of Clueless Gamer, mainly cause I wasn’t the audience for it, but this doesn’t seem to be for anybody. Just an unfunny man creeping out a woman.


it’s hard to remember there was a time when conan was funny and/or relevant

Hasn’t… “Conan is sort of a gross weirdo around pretty ladies” sort of been his entire schtick? He’s been doing it for something like 30 years. It’s typically so over the top that there’s no way of mistaking it for serious.

That being said, Conan has begun to lose a lot of his punch in recent years, yeah. Ever since the move to TBS after the whole Leno debacle it’s slowly felt like he’s been losing his bite. He went from one of my favorite late night hosts to somebody I barely pay attention to these days.

Ah, America’s answer to Game Center CX is finally faltering, eh?

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I dont think anyone is saying he’s seriously hitting on Kate, and it being his shtick doesnt make it any less uncomfortable.


The best part of it was her getting super into the game and kicking ass at it, but that was barely shown and never emphasized instead continuing to go back to the well of him hitting on her over and over. A well that wasn’t funny to begin with, since that’s got nothing to do with the game. The humor of clueless gamer is how he interacts with and responds to these games.

I would have thought that his level of lowbrow would be perfect for stupid “oh my god a girl is good at a video game!!!???” jokes (also not that funny but that’s where his jokes are usually at) but apparently I was giving him too much credit even for that.


Most celebrity appearances on Clueless Gamer segments at least have some relevance or through line to the game they’re playing. In this case it was all about Conan hitting on Upton and Cuphead itself was barely a footnote. Cuphead deserved better than this segment.

Also, this might just be a personal thing but I always felt weirded out about how many middle-aged dudes drool over Kate Upton, who is currently 25 years old and was around 22 when she first got a cover on Sports Illustrated. (Conan is 54!!)

I really like Conan but his flirting bits are supposed to be funny but happen so often that it comes off as a ploy to be genuine. This clip is funny overall but you can actually see the guest’s frustration when she catches him staring at her chest. He was being lascivious (and not for a comedic bit) and she rightly called him out for it. Then Conan and Andy basically blaming the victim for her outfit is off putting.

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I’m generally a fan of Conan, I just hope that the creepy lech schtick is tired joke that sometimes gets away from him and we don’t find out in twenty years that he’s been another sexual predator shielded by the patriarchy this whole time.