Raw Deal (1948)

Joe Sullivan (Dennis O'Keefe) is itching to get out of prison. He's taken the rap for Rick (Raymond Burr), who owes him $50,000. Rick sets up an escape for Joe, knowing that Joe will be caught escaping and be shot or locked away forever. But with the help of his love-struck girl Pat (Claire Trevor) and his sympathetic legal caseworker Ann (Marcia Hunt), Joe gets further than he's supposed to, and we are posed with two very important questions: Is Joe really the cold and heartless criminal he appears to be, or is there a heart of gold under that gritty exterior? And does Joe belong with the tough, street-wise Pat, or with the prim, moralizing Ann?