Robert Redford John Gage Demi Moore Diana Murphy Woody Harrelson David Murphy Seymour Cassel Mr. Shackleford Oliver Platt Jeremy Billy Bob Thornton Day Tripper Billy Connolly Auction M.C. Rip Taylor Mr. Langford Pierre Epstein Van Buren Joel Brooks Realtor Pamela Holt David's Girlfriend Nicholas Georgiade Croupier Danny Zorn Screenwriter Kevin West Screenwriter Tommy Bush David's Father Mariclare Costello David's Mother Myra J. Craps Woman Edwonda White Craps Woman Frankie J. Allison Craps Box Man Joseph Ruskin Pit Boss Joe La Due High Roller Ben W. Fluker Roulette Croupier Richard Livingston Mike Joe Bays Jeffrey Selma Archerd Auction Bidder Alan D. Purwin Helicopter Pilot Herbie Hancock Himself Ashlyn Gere Body Double (as Kim McKamy)