The 40-Year-Old Virgin (2005)
The 40-Year-Old Virgin is another comedy where, like with Observe and Report, many scenes are meant to be uncomfortable in order to make the audience cringe. That extends to a terrible scene in the bedroom when Steve Carell’s Andy fools around with Elizabeth Banks’ Beth.
The basic premise of the scene is that Beth is very sexually aggressive and Andy (as our titular virgin) is not. This leads to her painfully biting his lip, whipping him with a belt, and generally making sex look completely miserable. Andy’s friends eventually rescue him from the situation, and we felt rescued too because we didn’t have to watch any more of this!