10. James Brown
What is it with musicians and rap sheets? This soul singer was give two concurrent 6 year sentences for aggravated assault as well as some other felonies. He only served 2 ½ years of this time. Although he fought for a long time with drug addition, he did get clean for some time before he passed away from pneumonia in 2006.
11. Don King
More memorable by his crazy hair than anything else, Don King started out his adult life as a common criminal back in the 1950’s and 60’s. King ran an illegal booking business and was arrested for various counts of arson, murder, manslaughter, and dealing drugs for which he eventually served 3 ½ years. (Can we all agree that he should have gotten more time than that?) But he seemed to be able to turn his life around and become a famous boxing commentator and personality. In 1983, King was pardoned for his earlier crimes.
12. Martha Stewart

Certainly not a hardened criminal, Martha Stewart famously served 5 months in a federal prison. Her conviction was based on insider trading, about which she lied to federal investigators. Martha served her time and likely made many, many crafts out of old cigarette butts found in the prison yard.