James Brown

The Godfather of Soul's criminal career got off to an early start when he was arrested for armed robbery at 16 and served three years in a reform school. Decades later, Brown would repeatedly find trouble, mainly for drug, weapon and domestic violence offenses. His most notable indiscretion came when he brandished a shotgun in his office, angered that someone was using his bathroom without permission. The police were called and set up a roadblock nearby that Brown drove through, and he led cops on a chase that went from Georgia to South Carolina and back. He eventually crashed into a ditch after the tires on his pickup were shot out. He served three years for a combination of weapon and assault charges.