18. O.J. Simpson
Charges: Unpaid taxes, stealing satellite reception, robbery, kidnapping, domestic violence, coercion, conspiracy
Number Of Arrests: 4
Since beating that infamous murder rap, Orenthal James has been trying to land in jail one way or another. Almost as if he knew he belonged there. First, the IRS came looking for his ass due to $1.4 million in back taxes. Then, while his house was raided for E pills, they found illegal satellite equipment. Finally, "The Juice" ran up on some memorabilia dealers in a Vegas hotel room at gunpoint and took "his" stuff back. He was charged with kidnapping and robbery. O.J. is now serving a 33-year sentence.