The Doorway to Hell

Lew Ayres plays as a young Chicago gang leader who is so successful that he becomes the underworld boss of the entire city. He meets Dorothy Mathews and immediately falls in love with her. However, Mathews is a gold-digger who is secretly in love with Ayres's best friend, Mileaway, played by James Cagney. Ayres ends up marrying Mathews, who continues to be unfaithful to him during her marriage. Ayres eventually gets tired of being a gangster and attempts to go straight.