Donnie Darko (2001)
For a babyfaced (but somewhat disturbed) Jake Gyllenhaal, the countdown to Halloween means more than just costumes and candy. Starring Jake along with Drew Barrymore, Patrick Swayze, Maggie Gyllenhaal, and Jena Malone, the indie flick has become a certified cult classic perfect for the season, especially due to the iconic line, "Why are you wearing that stupid man suit?" Just make sure you brush up on your space-time continuum knowledge before you press play.
[Photo via Facebook]
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