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I'd put The Dude at #1. If you were a true fan, you'd know that Jeffrey Lebowski in the movie is "the other Jeffrey Lebowski, the millionaire!" to quote Walter. Jeff Bridges' character, The Dude, is the real winner, and I think is the best movie character of all time.
Now, if you really were going for the millionaire, my apologies, but that would make me lose respect for the rest of your list.
Donnie Darko too, he's great.
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However livin' better now, Gucci sweater now..
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