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I don't have a top 5, so I'll just put five movies I like a lot (a bit of a random sampling of my top 50ish):

Princess Mononoke-Its been my favorite Ghibli film since I first saw it. The entire story is amazing, the animation is beautiful, the characters are interesting, the themes are spot on. Brilliant movie.
2001: A Space Odyssey-So much to like about this movie, from its realistic depiction of space, to its handling of AI, to its brilliant direction...
Blues Brothers-Greatest car chase scene in movie history, and its got some pretty great music too.
Paprika-All of Satoshi Kon's works that I've seen have been brilliant, but Paprika is my favorite so far. So twisted and imaginative and beautiful.
Evil Dead 2-The first 30 minutes of this film are, in my opinion, the greatest 30 minutes of the horror/comedy genre, with the last 30 minutes of Evil Dead 1 probably being the second greatest...