The Moment: On September 2010, T.I. and his wife Tameka "Tiny" Cottle were arrested on drug charges in Los Angeles.
The Disappointment: Since T.I. was on probation at the time of his arrest, he was forced to go back to prison to serve the 11-month sentence that he's still serving right now.
How T.I. Overcame It: Ideally, T.I. will get out of jail at the end of this month and put all of his legal troubles in the past. But as we've learned time and time again, T.I. seems to enjoy doing things the hard way.