10 Things I Hate About You is smart, funny, and witty, and almost no one would know it is actually a modern adaptation of William Shakespeare’s comedy The Taming of the Shrew. While other teen comedies feel very surface-level with their jokes and characters, 10 Things I Hate About You goes more in-depth with the varying levels of friendships — it does help that the main cast became such good friends almost immediately. This is the film that put Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt on the Hollywood map, so many fans are very thankful to the casting director.