30. 10 Things I Hate About You (1999)
The Taming of the Shrew may have drawn yawns from teenagers in classrooms around the world, but it nonetheless served as the basis for a rom-com that’s still beloved by an entire generation.
A cast of rising stars fronted by Julia Stiles, Heath Ledger and Joseph Gordon-Levitt bring Shakespeare into the world of teen comedy, and in all honesty it works a lot better than it has any right to.
Quick-witted and without an ounce of cynicism, 10 Things I Hate About You is formulaic almost to a tee, but sidesteps the pitfalls that drag down many other rom-coms to stand tall as one of the genre’s cleverest spins.