The most famous drug lord in human history had crazy wealth and a crazier prison sentence. His prison escape was unmatched but being on America's radar would be his downfall.

Crazy Joe was able to successfully turn on his boss and gain some territory in New York City for the Gallo name, before his tragic ending.

Angelo Bruno had the nicknames "docile" and "gentle" for using strategic ways of handling business instead of violence, like so many other mobsters at the time.

Our first truly, international episode. The Kray Twins started the gang called the "The Firm" who was not to be messed with in Great Britain. 

Mickey Cohen started off as a troubled teen, became a professional boxer, then led to being in many social circles of Los Angeles.

"Momo" means crazy, and Sam Giancana may fit that definition perfectly. He took over the city of Chicago and found himself amongst many friends, including Sinatra, the Kennedys, and even Castro. However, this would all lead to his mysterious death.

She was one of the most famous outlaws in Oklahoma who kept getting involved with the wrong guys.

Drucci helped keep the Northside gang in Chicago together after the fall of Dean O'Banion. He was a jokester, a hitman, and had quite a downfall to the hands of a police officer. 

Joe the Boss could be argued as the first boss of bosses. He ruled the New York City underworld and got greedy, which would ultimately lead to his death.

Torrio was called "The Fox" because of his cunning and finesse strategy. He became one of the most feared men in the gangster battle over the territory of Chicago.