T.I. is one of the most successful rappers of the 2000s, and his stints in jail only added to his mythology. He infamously filmed a promotional video behind bars in Georgia in 2004, per MTV News, and he dropped his seventh studio album in 2010 while serving 11 months in federal prison — he was arrested on drug charges in Los Angeles and was found to be in violation of his probation, which prohibited him from committing a crime or illegally possessing controlled substances. Prior to that, he was imprisoned in 2009 for weapons possession, per The Hollywood Reporter.