Robert Redford as John Gage

Demi Moore as Diana Murphy

Woody Harrelson as David Murphy

Seymour Cassel as Mr. Shackleford

Oliver Platt as Jeremy

Billy Bob Thornton as Day Tripper

Billy Connolly as Auction M.C.

Rip Taylor as Mr. Langford

Pierre Epstein as Van Buren

Joel Brooks as Realtor

Pamela Holt as David's Girlfriend

Nicholas Georgiade as Croupier

Danny Zorn as Screenwriter

Kevin West as Screenwriter

Tommy Bush as David's Father

Mariclare Costello as David's Mother

Jedda Jones as Craps Woman

Myra J. as Craps Woman

Edwonda White as Craps Woman

Frankie J. Allison as Craps Box Man

Joseph Ruskin as Pit Boss

Joe La Due as High Roller

Ben W. Fluker as Roulette Croupier

Richard Livingston as Mike

Joe Bays as Jeffrey

David Rees as Businessman

Irene Olga López as Gage's Maid

Israel Juarbe as Citizenship Student

Lydia Nicole as Citizenship Student

Iqbal Theba as Citizenship Student

Maurice Sherbanee as Citizenship Student

Elsa Raven as Citizenship Student

Matthew Barry as Architecture Student

Chi Muoi Lo as Architecture Student

Art Chudabala as Architecture Student

Hilary Reynolds as Architecture Student

Selma Archerd as Auction Bidder

Robert 'Bobby Z' Zajonc as Helicopter Pilot

Alan D. Purwin as Helicopter Pilot

Sheena Easton as Herself

Herbie Hancock as Himself

Ashlyn Gere as Body Double (as Kim McKamy)