No time is ever a good time to go to jail, but T.I. has always managed to find the absolute worst times to go. In 2004, right when he was starting to live up to his self-appointed “King of the South” title with his hit single “Rubberband Man,” T.I. was nabbed for parole violation and sentenced to three years in jail. He served one year of the sentence and immediately got back to work by engaging in and prevailing in a rap beef with Lil Flip in 2005 and then releasing his classic album King in 2006. T.I. would ride the wave of success for about year until he found himself in trouble again when he was arrested just blocks away from the BET Hip Hop Awards in Atlanta where he was caught trying to buy some guns in a parking lot. He was ordered to house arrest after paying a $3 million bond and was eventually sentenced to 366 days in prison. In the time leading up to serving the sentence he recorded verses for Yung LA’s “Ain’t I” and Mary J. Blige’s “Good Love” referring to his impending sentence a hosted a farewell concert in Atlanta. When he got out he seemed to be doing better than ever releasing the biggest album of his career, Paper Trail, landing high-end endorsements and movie roles. He started recording a new album to be titled King Uncaged, but in September 2010 he and his wife Tiny were busted for drugs in Los Angeles and was sent back to jail for 11 months. Before he went in he changed the title of his album to No Mercy. The album went Gold but got mixed reviews. T.I. would again get out of jail in 2011 and he hasn’t been back. Since then he has released two chart topping albums, went independent and became a shareholder in Jay Z’s Tidal.

Verdict: HURT. T.I. continues to bounce back but lawyer fees rack up after while. His constant returns to jail slowed up his Grand Hustle label to the point that artists on the label weren’t releasing records and forced him to restructure the company multiple times.

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