Year Arrested: 1938

Crime: Seduction and adultery

Let's take a second to thank the higher powers that we don't live in 1938. Sinatra allegedly promised a woman his hand in marriage if they boned, and since she was a lady of good repute he was arrested. The charges were dropped when authorities learned that the woman was married, increasing Sinatra's actions to bawse status. He later become known as The Chairman of the Board, but in his youth Sinatra was rocking a sharp suit and a devil-may-care 'do that definitely attracted ladies of both good and ill repute.