Chuck & Buck (2000)

There are two types of people in this world: Those who've seen Chuck & Buck (2000) and those who haven't. This is a movie not easily forgotten thanks to screenwriter and leading man Mike White's commitment to cringe comedy. White stars as amateur playwright Buck, while Chris Weitz (a successful writer and director in his own right) plays Chuck, or rather Charlie, a successful music industry exec engaged to Carlyn (Beth Colt). When the two reconnect, Buck unlocks Charlie's repressed memories of encounters with the stunted man-child he now sees before him when he was younger. Yes indeed, Chuck & Buck like to Fuck... or they Liked to, anyway, which was the rallying cry for the experimenting duo, but while Chuck has moved on and become Charlie, Buck is still hung up on his old flame. The two finally do get down to fucking, with both Mike White and Chris Weitz going shirtless to make out before White starts going down on Weitz! The good news is that this repairs whatever trauma Buck might have repressed himself, and the flick has a weirdly happy ending.