I've been working on this list for awhile, and I'm still not entirely happy with it. I didn't want to put in the work to make a top 50 list, but I was similarly unable to cut it down below 30. While I think all of these films are objectively great, and I could make a reasoned argument for each, a lot of this is based personal favoritism as well
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and i have to ask, did you consider Igby Goes Down and Donnie Darko for this list?
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Some of the other movies that didn't quite make it: Milk, Man on Wire, The 40 Year Old Virgin, Paris je t'aime, The 25th Hour, Mysterious Skin, etc.
Now I'm kinda wishing I had made room for Igby, damn you <3
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