The latest edition of Clueless Gamer has Conan O'Brien going co-op in the retro cartoonish Cuphead with model Kate Upton. While the entire episode is - as always - supposed to be lighthearted and fun, this one falls flatter than some of O'Brien's jokes.

The premise of the scripted sequence is O'Brien's infatuation with Upton, and he becomes increasingly creepy as the segment progresses. Conan dies on several occasions while Upton holds her own, but in one part, O'Brien and Upton share a controller in an obvious attempt to further the tried and tired cliche of a session.

The good news is we do get a good look at Cuphead, which is coming exclusively to Xbox One on September 29 after it was delayed last year. The platformer is drawn and animated in an old-school 1930s-ish cartoon style. The gameplay looks fun and should be a nice dose of nostalgia for gamers who enjoy the older cartoon style. 

The bad news is this segment is a disrespectful misogynistic disaster that insisted on pushing O'Brien's stalker-esque tendencies throughout the session. Upton likely passed off on the script and played along, but in the end it was just an uncomfortable mess that focused more on O'Brien being an ass than anything else. Yes, Clueless Gamer uses games as a starting point for comedy and is more about O'Brien's inane banter than showing off games, but this episode was even more awkward and uncomfortable than usual. And in the current climate, the segment gives the word clueless new meaning.

Upton has had her own share of exposure to games, starring in several multi-million dollar commericals for the poorly reviewed free-to-play mobile title Game of War.