Hard Eight (1996)

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.—Jon Reeves