Al Capone (a.k.a. 'Scarface'), one of the most famous American gangsters, rose to infamy as the leader of the Chicago mafia during the Prohibition era. Before being sent to Alcatraz Prison in 1931 from a tax evasion conviction, he had amassed a personal fortune estimated at $100 million dollars and was responsible for countless murders.
This is a picture of what a 1930's Hollywood Gangster looks like. I chose this picture because in the book Monster, the gang members are nothing like this "gangster". The gangsters in Monster and guys who wear oversized shirts with either blue as their main color, or red.