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The End of Evangelion (3 episode ending movie, bout 90 mins total) (this is anime for those of you people who don't watch any) was really disturbing to me the first time I saw it about 4-5 years ago. I watched it over 2 more times in a row after that because I was trying to figure it out. I really love that movie now though, and it has some great thoughts on life that you can get into...
as for regular movies, a Clockwork Orange freaks me out... though I find no deep meaning in it for me...
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