3. "My Own Private Idaho" (1991)

Like James Dean, River Phoenix seemed born to project youthful angst on film before he left the world too soon, and Gus Van Sant brought this out of him better than any other filmmaker in his extremely loose take on Shakespeare's Henry IV. When he's not following the whims of clients or the lead of wayward rich kid Keanu Reeves, Phoenix's narcoleptic street hustler is just looking for someone to show him genuine, sustained affection. Given his line of work and his tendency to pass out uncontrollably, that's a heartbreakingly tall order.

Angst-ometer rating: 8

Sample quote: "I've been tasting roads my whole life."

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