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This is tough since I really like both movies, but for completely different reasons. Man, 1999 was a great year for movies!
This one's pretty hard. One of the best dramas vs. one of the best action movies. Matrix has its awesome looks, american beauty has Kevin Spacey. This is a total draw.
The only reason i give the point to The Matrix is because there are a few lines in Beauty by Thora Birch (playing Angela, the blond pal) that don't feel completely natural. Maybe you could say the same about Matrix, but for me it stood out more in Beauty the last time i saw it.
I'll pick Kevin Spacey over Keanu Reeves.
Neo for the win. But it's close...