24. Donnie Darko (2001- Richard Kelly)
Amidst a 90s craze for somber and dark themes, Donnie Darko crisscrosses the thin line between philosophy and insanity. The movie follows a sleep-deprived, depressed and schizophrenic teen. It depicts a mystical and sinister world that drifts in and out of reality. While this movie flew under the radar when it was first released in 2001, it gained vast critical acclaim and became a cult classic.