The film that catapulted him into the spotlight, Good Will Hunting earned Damon his first Oscar nomination and win for screenwriting, which he shared with BFF Ben Affleck. The story, about a young man who hides his brilliance while cleaning the halls of MIT, is funny, smart, and heartwarming. Plus, that adorably floppy haircut? Classic '90s Matt Damon.
Good Will Hunting (1997)
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