1. T.I.
Legal name: Clifford Joseph Harris Jr.
Offense: T.I. and his wife Tiny were arrested on drug charges in Los Angeles which led to T.I. being spending 11 months in prison for violating the terms of his probation, specifically for possessing ecstasy, testing positive for opiates, and associating with a convicted felon. Less than 48 hours after his release, T.I. was sent back to federal custody due to a dispute involving T.I. taking a luxury bus from a prison in Arkansas to a halfway house facility in Atlanta.