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My vote was a tough one between "The Good, the Bad, and the Ugly" and "The Searchers." I ultimately went for GBU because it's the quintessential guy's film. I must've watched it 12-15 times already. It's got the cool Ennio Morricone music, the ubercool three-way Mexican standoff, and that scene where Clint lights the cannon. Gets me every time.
But I'll have to give my props to "The Searchers." I'm no John Wayne fan, but the Duke really proved himself in this movie. He was a nihilistic anti-hero before Clint Eastwood made it cool. A complex racist who hates Comanches, yet knows their language and customs better than anyone else. This film is incredible in its subtely, and if you're not paying attention you miss a good portion of the plot. I originally rented out because several directors --- Scorcese, Spielberg, Lucas, Milius --- listed this as their favorite, and after viewing the movie, it wasn't hard to see why.
(And, thanks to Lucas, I can't watch certain scenes in "The Searchers" without thinking about similar scenes from Eps II and IV; scenes that Lucas had intentionally replicated to pay homage to the film.)
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