10 Things I Hate About You (1999)
This is the movie that locked in Heath Ledger's hotness. It came before The Patriot, A Knight's Tale (another great rom-com) and Brokeback Mountain. Alongside him in the cast are Julia Stiles, Joseph Gordon-Levitt and Gabrielle Union.
Little sister Bianca can't date until her antisocial big sis Katarina does, and that's not happening anytime soon. In order to force the issue, Bianca gets her guy to bribe Patrick (Ledger) to date Kat. While we know they'll fall in love, there are plot twists that show why Kat won't date and that a hero isn't the most obvious person in the room.
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