Jake Gyllenhaal: 5 Awesome Performances And 5 That Sucked

4. Donnie - Donnie Darko

Speaking of which, the role that broke Gyllenhaal in Hollywood remains one of his strongest to date. It's unknown whether he went method and took some of the chemical, ahem, enhancements that gave Donnie the dreamy, spaced-out look and speech pattern depicted throughout Richard Kelly's surreal love letter to eighties pop culture-cum-existentialist time travel flick, but if not, he sure does a good job playing a crazy person. Or perhaps not so crazy: throughout the film it's never quite clear if Donnie's nightmares are actual prophetic visions, or if his parents sent him to therapy for a reason. Regardless, Gyllenhaal sells Donnie as both a weird suburban superhero, a burn out teen, and a seriously troubled young man whose ongoing harassment by a guy in a bunny mask seems like the least of his problems. Plus there's a sex scene between Jarhead and Lettie from Howl's Moving Castle, etc.