Sydney (Philip Baker Hall) is a veteran gambler in his sixties who still spends his time at the casinos. When he meets John (John C. Reily), a loser with no money at all, he sees him as a son and tries to help him. He takes care of him and teaches him all the tricks of his work. He also helps him to make a relationship with Clementine (Gwyneth Paltrow), a young girl who works at the casino as a waitress. John doesn't seem to be bothered by the fact that Clementine is also a hooker, but soon something happens that turns their lives upside down.