Time Served: 7 months in 2009, 10 months in 2010 and 2011
The rapper was arrested in 2007 for attempting to purchase unregistered machine guns and silencers. As a result, T.I. spent seven months at an Arkansas prison in 2009, followed by three months at Dismas Charities halfway house in Atlanta in early 2010. He was still under probation in September 2010 when he and his wife, Tameka Cottle, were arrested on drug possession charges in West Hollywood, Calif. The rapper returned to federal prison for 10 months for violating his gun conviction parole.