Movie: Donnie Darko (2001)
Writer: Richard Kelly

Donnie Darko is definitely one of the riskiest and wildest directorial debuts imaginable. A first-time writer and director, the then-26-year-old Richard Kelly both confounded and impressed cinephiles in 2001 with the mind-bending Donnie Darko, an eccentric high school dramedy/coming-of-age flick that includes everything from time travel to parallel universes and a 6-foot-tall rabbit named Frank.

Since the titular character (played by Jake Gyllenhaal) suffers from paranoid schizophrenia, Donnie Darko's bizarre ideas and imagery are always left up to the viewer's interpretation: Is it all really happening, or is this all just in Donnie's unstable mind? It turns out that latter option is correct, though in the most literal sense. The film is nothing more than a long-form hallucination experienced by Donnie right before an airplane's jet engine comes smashing through his bedroom ceiling and terminates the poor guy.

The fascinating thing is, however, that Donnie Darko's tragic outcome is quite optimistic—unhappy in life, the fake events that Donnie imagines give him the pleasantries and fulfillment that he was never able to achieve in reality. Including, of course, the chance to hook up with a cutie like Jena Malone. Even paranoid schizophrenics need some ass in their lives.