Just one year after portraying a math genius in Good Will Hunting, Matt Damon returned to the big screen as a poker genius in Rounders. He loses $30,000 to a Russian mobster, which is never a good thing. He's given five days to get it back, and spends the rest of the film frantically trying to put the money together. The ultimate lesson seems to be that if you're down a ton in gambling, just keep gambling more and more and eventually you'll figure something out. It was a modest hit, but it's retained a devoted following.