Good Will Hunting
A janitor at MIT solves the blackboard problem, and two unknown actors from Cambridge win an Oscar for writing it. Robin Williams on a park bench, Elliott Smith on the soundtrack, and "It's not your fault."
#Matt Damon
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Rounders
Matt Damon as a reformed card shark pulled back to the table, Edward Norton as the friend who keeps dragging him there, and John Malkovich chewing Oreos as a Russian mobster named Teddy KGB. A modest 1998 release that a generation of poker players later adopted as their sacred text.
The Bourne Identity
A man is pulled from the Mediterranean with two bullets in his back and no memory — but his hands remember everything. Matt Damon's amnesiac assassin made spy movies fast, grounded, and paranoid — and the decade's action cinema followed his lead.