This film isn't just for chicks, it's for everyone! 10 Things I Hate About you was an instant hit and became permanently ingrained into pop culture history. Released in 1999, it starred Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik. Like a few other films on this list, it is actually a modern-day adaptation of old literature. In this case, Shakespeare's Taming of the Shrew.
10 Things I Hate About You was a massive success and propelled the careers of Stiles and Ledger, who were relatively unknown at the time. A new student at school, Cameron (Gordon-Levitt) develops an immediate crush on Bianca (Oleynik). Unfortunately, her father has a strict rule about boys: no dating until your sister does. Her sister, Kat (Stiles) is a rebellious misfit, so Cameron enlists another misfit, Patrick (Ledger) to romance her.