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Owney Madden bootlegger and owner of the Cotton Club: rumored to be Mae West's lover and chief financial backer for her show "Sex"

George Celino Barnes, or better known as "Machine Gun Kelly," was an American gangster who's most famous crime was the kidnapping of business man Charles F. Urschel. He also committed crimes involving bootlegging and armed robbery.

Albert Anastasia (pronounced ah-nah-STAH-zee-ah) (born Umberto Anastasio, September 26, 1902 – October 25, 1957) was one of the most ruthless and feared Cosa Nostra mobsters in American history. A founder of the American Mafia, Anastasia ran Murder, Inc. during the prewar era and was boss of the modern Gambino crime family during most of the 1950s. Anastasia died in what was probably the most sensational assassination in mob history.

Benjamin Bugsy Siegel another famous (and crazy) gangster. He returned to NY from California during the Murder Inc. trials to kill any gangsters who may have talked to the police. He built the Flamingo in Las Vegas a few years later and stole money from the mob. He was killed in 1947.

Zazzlefrom Zazzle


John Dillinger- 1930s Gangster Real men are old school gangsters:)

Those famous words “Boop-Oop-A-Doop” that are so famously associated with Betty Boop, were first sung on stage in the Cotton Club by a jazz singer named Baby Esther.

Owney Madden, left, suspected but unconvicted racketeering boss, is escorted by detective Thomas Horan shortly after Madden was ordered on February 13, 1932, to report to Sing Sing as a possible parole violator. He was en route to the Tombs Prison in New York pending a hearing two days later.

Alphonse Gabriel "Al" Capone (January 17, 1899 - January 25, 1947), commonly nicknamed Scarface, was an Italian American gangster who led a crime syndicate dedicated to the smuggling and bootlegging of liquor and other illegal activities during the Prohibition Era of the 1920s and 1930s.

Famous gangster frank Castillo. Came a famous gangster from hanging around others.

Richard “The Iceman” Kuklinski is one of the most prolific contract killers ever to have worked for the Mafia. Having taken his first life when was just 13, he claimed to have personally committed as many as 250 murders.