Robert Boris Director, Screenwriter Rob Lowe Jesse James Actor Bill Paxton Frank James Actor Randy Travis Cole Younger Actor William Atherton Allan Pinkerton Actor Dana Wheeler-Nicholson Annie Actor Maria Pitillo Zee Actor Luke Askew Lone Rider Actor Sean Patrick Flanery Zack Murphy Actor Alexis Arquette Charlie Ford Actor Todd Field Bob Younger Actor John Pyper-Ferguson Clell Miller Actor Nicholas Sadler Arch Clements Actor Tom Chick Detective Whitcher Actor Mary Neff Widow Miller Actor Richard Maynard John Sheets Actor Jim Flowers Bob Ford Actor Mari Askew Ma James Actor William Michael Evans Jesse Jr. Actor Lyle Armstrong McGuff Actor Cole S. McKay Sheriff Baylor Actor Dennis Letts Railroad C.E.O. Actor John Stiritz Ruben Samuels Actor Micah Dyer John Younger Actor Jackie Stewart Governor Crittendon Actor Chad Linley Archie Samuels Actor Rhed Khilling Stage Driver Actor Jerry Saunders Northfield Teller Actor D.C. Dash Goff Engineer Actor Robert Moniot Young Captain Actor Norman Hawley Baptist Preacher Actor Cassian Elwes Producer Elliott Kastner Producer Mark Amin Executive Producer Walt Lloyd Cinematographer Christopher Greenbury Film Editing Mark McKenzie Original Music Michael Perry Production Design Scott Plauche Art Director Tracy Russell Set Decoration Maurin L. Scarlata Set Decoration Betty Pecha Madden Costume Design Ed Mitchell Casting Robyn Ray Casting