9. She’s All That (1999)

One of the ’90s most successful romantic comedies, She’s All That follows Zachary Siler (Freddie Prinze Jr.) as he attempts to turn “uncool” art student Laney Boggs (Rachael Leigh Cook) into the prom queen in just six weeks.

The issue here should be pretty self-explanatory, but when you really watch the scene of Zach making the bet, his attitude towards women is truly disgusting.

Upset that his girlfriend has left him for another guy, he claims that her popularity and status is all manufactured, and that without him she’s nothing. He believes that any girl he deems worthy of being on his arm will, by merit of his company alone, rule the school, and while it may seem like he was goaded into it by his friends, this really isn’t the case.

In fact, both of Zach’s best friends seem to think him delusional, but his cocksure attitude seals the deal for poor Laney, who is then subjected to weeks of his clumsy advances and predatory deception.

She’s All That is more dark thriller than romantic comedy, with a boy using his status and popularity to influence and manipulate a girl into becoming “better”.

Not only was nothing wrong with Laney to begin with, but the fact that she eventually falls for Zach just promotes a message that if men behave like they’re superior to women, they’ll be rewarded with love.

Don’t live your life like this, kids.