Heath Ledger's greatest performances

7. "10 Things I Hate About You" (1999)

Including Ledger's Hollywood breakthrough may seem questionable, but take another look at this better-than-average teen movie. The pleasantly clever spin on Shakespeare's "The Taming of the Shrew" is buoyed by a capable cast (including Julia Stiles, Joseph Gordon-Levitt, Allison Janney and Gabrielle Union) and showcases Ledger's underutilized knack for light romantic comedy. Bonus points for his "Can't Take My Eyes Off You" grandstand song-and-dance and for delivering a line about "beer flavored nipples" with a straight face.