2. Wedding Crashers (2005)

When talking about the buddy comedies of the ’00s, it’s a pretty safe bet that there’s at least a few jokes in there that haven’t aged well, but Wedding Crashers really takes the cake and smashes it into the audience’s face.

John (Owen Wilson) and Jeremy (Vince Vaughn) are best friends and self-proclaimed womanizers who crash weddings in order to meet women. But when John falls for a woman he meets at one of these weddings, things begin to get complicated. The friends are invited to a weekend getaway at her family estate, where they each try desperately to maintain their ruse, bed their chosen women, and keep the party going.

No, this isn’t one of those where the issue is in the movie’s premise (although there’s certainly enough there to pick out one or two issues), but with one of the movie’s more unsavory “jokes”.

One evening, while settling down for the night, Jeremy is accosted by Gloria, his chosen date, who promptly ties him to the bed. He protests, but she ignores him. He asks her to stop, so she gags him and strips naked before climbing on top of him and doing her thing, all while Jeremy screams through his gag. Probably a good time to reiterate that this movie is intended to be a comedy, not a horror.

Not only is Jeremy sexually assaulted, but when he tells his best friend about the ordeal, he’s dismissed out of hand. No sympathy, no compassion, not even a passing remark of support. Despite Jeremy’s intention of leaving the estate, John makes him stay and spend more time with his abuser.

Absolute laugh riot, isn’t it?