Jeff Bridges as Christopher 'Skipper' Sheldon

Caroline Goodall as Alice Sheldon

John Savage as McCrea

Scott Wolf as Chuck Gieg

Jeremy Sisto as Frank Beaumont

Ryan Phillippe as Gil Martin

David Lascher as Robert Marsh

Eric Michael Cole as Dean Preston

Jason Marsden as Shay Jennings

David Selby as Francis Beaumont

Julio Oscar Mechoso as Girard Pascal

Zeljko Ivanek as Sanders

Balthazar Getty as Tod Johnstone

Ethan Embry as Tracy Lapchick

Jordan Clarke as Charles Gieg

Lizbeth MacKay as Middy Gieg

Jill Larson as Peggy Beaumont

James Medina as Cuban Commander

James Rebhorn as Tyler

Nicole Ann Samuel as Girl in Brothel

Becky Ann Baker as Ms. Boyde

Camilla Overbye Roos as Bregitta