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Brad Pitt, 2000

I'm telling you, it's all about who you're paired up with. Brad Pitt became the first two-time solo sexiest man alive winner in 2000, the same year he married Jennifer Aniston. Having starred in Fight Club the year prior and Snatch the year he won, Brad would go on to be in Ocean's Eleven — a movie that seems to be a good-luck charm for the sexiest men alive.

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