This movie never fails to make me smile. A romcom with a Shakespearean backstory plus the universal themes of high school awkwardness and teenage angst? Yes please. This movie has everything from musical numbers to amazing 90s fashion. If that's not enough to pull you in, there's the stellar performances of the main cast, including Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt, to name a few. Kat, the main character, has a heart of gold that drives the plotline and every time I watch this movie, I am reminded by what an icon she is.
–Recommended by Andrea