20. Donnie Darko (2001)
Director: Richard Kelly
Stars: Jake Gyllenhaal, Jena Malone, Drew Barrymore, Noah Wyle, Patrick Swayze, Mary McDonnell, Maggie Gyllenhaal
By now, it's safe to call writer-director Richard Kelly a one-hit wonder, but, shit, his only movie worth talking about is a brain-pummeling knockout. Catching critics and moviegoers totally off guard back in 2001, Donnie Darko, a then-26-year-old Kelly's feature debut, introduced a fearless young director who wore his geek stripes proudly. It's an '80s-set teen drama subverted by a shitload of genre tropes, centering on a super-smart high school loner, Donnie Darko (a terrifically sardonic Jake Gyllenhaal), who hallucinates that a dude in a bunny suit warned him about the world's end and begins to accept time travel as a viable practice.
There's much more at stake than that, but we'll fall back from any further summarizing; it's best to experience Donnie Darko with as little pre-existing knowledge as possible. Kelly's feat is all the more remarkable when you realize that an unproven guy in his mid-20s was capable of conceiving such a large-scale, witty, and disturbing fever dream. It's just a damn shame that Kelly's talents aged more like unrefrigerated cheese than fine wine.