9. CHARLES ARTHUR "PRETTY BOY" FLOYD (1904-1934)

Calling Card: He used a machine gun during every robbery.
Casualties: Floyd was suspected to be involved in the Kansas City Massacre, a incident where four police officers were killed.
Complex Says: Unlike the “Pretty Boy” Floyd we know today, who gambles all his money on Miami Heat games, the original Floyd was a man of the people.

Charles Arthur Floyd, who got the "Pretty Boy" name from a bank teller he was robbing, was known for his Robin Hood activities. He would destroy mortgage papers to free people from debt and hand out bundles of money after he robbed a bank. These actions made him one of the era's most romanticized criminals.