10 Things I Hate About You (1999)

Padua High has a guidance counselor writing a romance novel between appointments, and she’s only the second strangest thing about the place. The first is that the whole plot runs on a rich kid paying a guy to date a girl, and the movie files that under cute. It has aged like gas station milk. Everything around it is way better than a teen comedy needs to be. Julia Stiles plays Kat like she’s personally annoyed the script exists, which is exactly right. Heath Ledger gets a bleacher serenade with a marching band and a security guard on his heels, the most committed move in teen movie history. Larry Miller as the panicking dad steals every scene he walks into. It’s Shakespeare with a late nineties soundtrack, and it still beats most teen comedies made since. A 7.0 because the cast is great and the premise is gross, and both things are true. $22 says you try writing your own list of things you hate about someone and it turns into a list of things you like.

What works: Julia Stiles and Heath Ledger have real chemistry, and Larry Miller turns an overprotective dad into a nonstop comedy act.

What doesn’t: The plot depends on boys secretly paying someone to date a girl, and the movie never really reckons with how gross that is.

Who it’s for: People who want a late nineties teen comedy with actual jokes and don’t mind a little Shakespeare sneaking in.