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1. Harold and Maude - no question the best. See it if you can find it, it's been recently reissued. Funny, sad, touching, and lots of smarts.
2. Rushmore - same as above only slightly less twisted as Harold.
3. The Graduate - does this count? It's about angst and ennui and Benjamin is probably only 21 (close enough to teenagedom).
4. Ghost World - for obvious reasons.
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