2. "Donnie Darko" (2001)
If it weren't for a tangent on Smurfette's sex life and a performance by grade-school dance sensations Sparkle Motion, Richard Kelly's bizarre but inspired feature debut would be a nonstop angst fest. As it is, with its subplot on a damaged Jena Malone and its suggestion that dying isn't as bad as things can get, this '80s-era look at the troubles, time warps and scary man-rabbit plaguing Jake Gyllenhaal's brilliantly acidic high schooler has only Menace II Society to compete with as the most fatalistic movie on this list.
Angst-ometer rating: 10
Sample quote: "You're right, actually. I'm pretty troubled and I'm pretty confused. And I'm afraid. Really, really afraid. But I think you're the f---ing antichrist."
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