Hard eight (1996) - Paul Thomas Anderson
John has lost all his money. He sits outside a diner in the desert when Sydney happens along, buys him coffee, then takes him to Reno and shows him how to get a free room without losing much money. Under Sydney's fatherly tutelage, John becomes a successful small-time professional gambler, and all is well, until he falls for Clementine, a cocktail waitress and sometimes hooker. Sydney is a veteran gambler in his sixties who still spends his time at the casinos. When he meets John, 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, 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.