2. O.J. Simpson
Criminal History: Robbery, kidnapping, domestic violence, coercion, conspiracy
Time Behind Bars: Currently serving a 33-year sentence
After beating a body or two in '95, Simpson spent a decade "looking for the real killer" and golfing—mostly golfing. He's run in to various legal troubles since his murder trial including a tax lien in '99 and an arrest for road rage after reportedly scratching a man's face during a heated argument about a blown stop sign.
O.J;'s currently serving time for an armed robbery in which Simpson and a group of men broke into a Las Vegas hotel room to steal sports memorabilia at gunpoint. The former Heisman winner will have to wait until 2017 for his first parole hearing.