14. Mike Tyson
Criminal History: Rape, road rage, possession of narcotics
Time Behind Bars: Three years
There may not be a more sympathetic convicted rapist than Mike Tyson. He has an absolutely deplorable criminal history that we mostly overlook because he was, like, really funny in The Hangover.
His most famous run-in came in '91 with the aforementioned rape of an 18-year-old beauty queen. "Iron" Mike always denied any wrongdoing but didn't exactly endear himself to anyone in a 2006 interview, "I just hate her guts. She put me in that state, where I don't know, I really wish I did now," Tyson said. "Now I really do want to rape her."