City Slickers. It truly was a product of its time, and by that, a :grillman: impregnating a 20 year old in a one-night-stand behind his wife's back is portrayed as a bad thing because the wife got upset about it. Oh, it doesn't end there, far from it, but that alone has sort of memory-holed it as far as I can tell.
Revenge of the Nerds had
spoiler
rape
as a plot point, a joke, and a heroic triumph of a protagonist character.
PCU is an astonishingly dated movie but at the same time is almost perfectly a prophetic example of :reddit-logo: style enlightened centrism and predates South Park for expressing the idea of "caring about things is stupid, do weed lol." It also has straw feminists and straw vegans to dunk on, and of fucking course the cryptofascists on campus are presented as only as bad as those loony leftists.
Overboard.
CW: Rape
spoiler
A few years ago they did a remake which kinda quietly bombed and pretty much everyone was like:
"Who the fuck thought this was a good idea to green light? The original had already become unwatchable at this point because even as charming as Kurt Russell is it's impossible to see him as anything other than a brainwashing rapist now."
If you have no idea what I'm talking about Google it. Exhibit A of rape culture in Hollywood romance comedies.
There was an old Clint Eastwood movie where
spoiler
the "hero" drags off a mouthy uppity feeemale and rapes her as a moment that was supposed to somehow be funny and show how cool the rapist is.