Rounders is a story of a pair of prep school buddies, Matt Damon and Edward Norton, who are a pair of poker sharks. Damon's used his winnings to pay for law school and Norton's gone on to other enterprises like identity theft which has landed him a stretch in prison.
Damon after being taken to the cleaners by Russian mob guy John Malkovich has given up poker for law school. Norton's finishing his stretch in the joint and as it turns out he owes Malkovich some heavy duty debt. He's needing some help, especially after leg breaker Michael Rispoli gives Norton a sample of what he can expect.
Damon owes Norton as well for not ratting him out on some prep school scam that could have gotten him expelled like Norton. Needless to say he goes back into the life.
I'm willing to wager (no pun intended) that because Rounders came out right after Good Will Hunting that this was a project intended for Damon and Ben Affleck. I think Ben probably showed good sense in thinking he was not quite right for the role. Certainly Norton who plays some really edgy characters was far better for the role of Lester 'Worm' Murphy.
Damon does all right for himself as the standup Mike McDermott. He also because he discharges the debt he owes Norton, realizes that he should follow his dream as well. What it is and how the film ends I won't say, but if you have a dream you have to follow it because you won't know if you don't try.
In addition to everything else Rounders is quite a look into the world of professional gambling. As Damon says even if you play it honest, it's far more skill than luck. You read the opponent, not the cards.
Rounders was a great career followup to the acclaimed Good Will Hunting for Matt Damon. Even if you're not a gambler by nature, this film will fascinate one.