Portrait of a Mobster (1961)

This movie portrays the rise and fall of 1920s gangster Dutch Schultz. While building his own mob ring, he romances Iris, the daughter of a man he killed. When Iris marries a cop, Schultz makes sure the cop goes bad and takes kickbacks from Schultz's organization. Iris goes back to the arms of Schultz, not knowing he's the man who killed her father.