Poker: Rounders (1998)
Most sports films lead to the big tournament, the final game, the last pitch. But while Mike McDermott (Matt Damon) pores over old World Series of Poker tapes and studies greats like Johnny Chan, his big event is a heads-up battle against a Russian gangster in a dingy underground poker room. His prize is that he and his friend, aptly named Worm, might get to keep their fingers if they can pay their debts. But along the way, Mike, a law student who'd rather have his life threatened in dingy underground poker rooms, realizes what's important to him, when to hold 'em, when to fold 'em, and that, while you can't lose what you don't put in the middle, "you can't win much either."