Enemy (2013). lots of people's least favorite Villeneuve movie, but I really liked it. no shot you'll have any idea what happened after just one watch.
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I want to put in my ticket for What Dreams May Come, one of Robin Williams more heartfelt and serious roles, and one rarely mentioned. You can "get" the movie on the first watch and only really begin to understand all the nuance and subtlety during the second or third run.
I'd go with Possessor by Brandon Cronenberg. I've only seen it once so far, and the unfolding of the story was such that you had to work for it. It wasn't impenetrably dense, but I definitely had to give it the attention it demanded.
Angel Heart. We discussed what happened in that movie for weeks while returning to the theater at least once more each, some three times
American Psycho for me. I had a lot of questions after watching it for the first time. It doesn't have what I'd call a "satisfying" conclusion, but that's what makes the movie what it is. It's kind of a mindfuck, and the subtle humour in it is just top notch.