Donnie Darko (2001)
Teenagers don't get much more disaffected than Jake Gyllenhaal's Donnie Darko, who begins his own film passed out on a dusty roadside with no memory of how he got there, and believes that the world is about to end because a giant talking rabbit tells him so. The angst may not be universal, but the film's peerless as a strange, haunting portrait of misunderstood youth.