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I would go for: 2001: A Space Odyssey / Inception / Good Will Hunting / Fight Club / 12 Angry Men I like things that are pretty easily watchable but also have something a little deeper going on behind the surface if you want to dig in a bit. It was hard paring out Pulp Fiction and The Shawshank Redemption. I haven't really watched a lot of the classic movies though because I usually feel they're too slow. They feel faster when watching with a group though, so I try to do that every now and then.