Cagney starred as Rocky Sullivan, a gangster fresh out of jail and looking for his former associate, played by Humphrey Bogart, who owes him money. While revisiting his old haunts, he runs into his old friend Jerry Connolly, played by O'Brien, who is now a priest concerned about the Dead End Kids' futures, particularly as they idolize Rocky. After a messy shootout, Sullivan is eventually captured by the police and sentenced to death in the electric chair. Connolly pleads with Rocky to "turn yellow" on his way to the chair so the Kids will lose their admiration for him, and hopefully avoid turning to crime. Sullivan refuses, but on his way to his execution, he breaks down and begs for his life. It is unclear whether this cowardice is real or just feigned for the Kids' benefit. Cagney himself refused to say, insisting he liked the ambiguity. The film is regarded by many as one of Cagney's finest, and garnered him an Academy Award for Best Actor nomination for 1938. He lost to Spencer Tracy in Boys Town. Cagney had been considered for the role, but lost out on it due to his typecasting. (He also lost the role of Notre Dame football coach Knute Rockne in Knute Rockne, All American to his friend Pat O'Brien for the same reason.) Cagney did, however, win that year's New York Film Critics Circle Award for Best Actor.