Frank Sinatra John Baron Sterling Hayden Sheriff Tod Shaw James Gleason Peter 'Pop' Benson Nancy Gates Ellen Benson Kim Charney Peter 'Pidge' Benson III Willis Bouchey Secret Service Detail Chief Dan Carney Paul Frees Benny Conklin Christopher Dark Bart Wheeler James O'Hara Jud Hobson Kem Dibbs Wilson Charles Smith Bebop Paul Wexler Slim Adams Clark Howat Haggerty John Beradino Trooper (uncredited) Richard Collier Ed Hawkins (uncredited) Roy Engel Driver Asking Slim for Directions (uncredited) Ted Stanhope Driver Asking Tod for Directions (uncredited) Charles Wagenheim Iz Kaplan (uncredited) Dan White Burg (uncredited) Lewis Allen Director Charles G. Clarke Director Erich von Stroheim Jr. Director Hal Klein Director