Director: Richard Kelly
Stars: Jake Gyllenhaal, Jena Malone, Patrick Swayze, Mary McDonnell, Maggie Gyllenhaal, Holmes Osborne
Lesson Learned: Drugs are bad...unless they're of the medicinal kind. In that case, take them often, otherwise you'll start talking to dudes in bunny costumes.

School movies, by definition, are traditionally straightforward—all that's required to sate the genre are a campus, somewhat interesting students, and relatable conflicts. The films on this list are all solid (After all, why else would they be included?), but the majority of them are, for better or for worse, conventional. Donnie Darko, on the other hand, overflows with ambition. The striking debut of writer-director Richard Kelly, it's your typical coming-of-age story filtered through time travel philosophies, a dude in a freaky bunny costume, someone named Grandma Death, and the spirit of David Lynch.

Jake Gyllenhaal, pre-A-list, stars as an eccentric high school outcast whose visions of a prophetic rabbit, named Frank, lead him to believe that the world's about to end; it doesn't help that his bedroom, without him in it, was recently firebombed by a broken-off jet engine. There's a multilayered tale of a teenager grappling with both his own psychosis, mortality, and adults' hypocrisy at the film's core. But Kelly's gonzo narrative is one of those flicks that demands repeat viewings before one totally comprehends its point. Thankfully, Donnie Darko is mesmerizing enough to never feel stale.