Hard Eight (1996)
Original title: Sydney
Release date; February 28, 1997
Synopsis
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.
Awards
1997: Independent Spirit Awards: : 5 Nominations including Best First Feature
1997: Los Angeles Film Critics Association: New Generation Award (Anderson)
1997: Boston Society of Film Critics Awards: Best New Filmmaker