T.I.'s brilliant career has seen its fair share of interruptions, primarily due to legal troubles that have forced the rapper to take time away from the stage in order to sit behind bars.
On Wednesday night, T.I. and his wife, Tameka "Tiny" Cottle, were arrested for alleged drug possession in Los Angeles.
The arrest is the latest in a series of offenses T.I. has been involved in during his lifetime.
He was released from prison earlier this year stemming from an October 2007 arrest after he was busted attempting to illegally purchase firearms.
T.I.'s 366-day sentence was his most infamous to date. Although he served less than a year in prison and finished his sentence at a halfway house, the case not only threatened to derail his career but, because he initially faced a lengthy sentence, could have seen him spend a large portion of his life incarcerated.
Prior to his most recent prison term, T.I. found himself on the wrong side of the law on more than one occasion. He's often referred to himself as a multiple felon in his rhymes.
But T.I. has rarely been arrested on drug-related offenses; most of his troubles stem from gun busts.
In fact, prosecutors in T.I.'s 2007 weapons case argued that the rapper had not faced the full-on consequences for a number of past offenses.
They cited a December 2001 arrest for gun possession, a November 2002 instance where he was carrying a 10mm pistol and a 2004 bust during which authorities found a silencer-enhanced weapon, loads of ammunition and photos of T.I. handling guns.
In 2004, T.I.'s pre-rap dealings finally caught up with him when he was busted on a parole violation just as his career was taking off on the heels of his breakout number, "Rubber Band Man."
The violation was in relation to a 1998 arrest and conviction in Georgia for distribution of cocaine, manufacturing and distributing a controlled substance and giving authorities a false name. T.I. was sentenced in that case to three years in prison and was released after serving one year.
Before his most recent stint in jail, T.I. seemed to place his past in the context of his bright future in hip-hop.
He told a group of reporters, fans and family members gathered at the Atlanta courthouse where he was sentenced that he was ready to begin the next phase of his life as a responsible adult.
"Although I am not thrilled about my next year and a day, I am pleased that I am beginning the process of putting this all behind me," he said. "Thank you, and I apologize to my family, to the young men, young women that I mentor. I hope that I can keep at least one, if not a million or more, from going down a similar path. I just want to say thank you."
Since he's been free, the rapper has repeatedly owned up to his mistakes and vowed to stay on the straight-and-narrow path.
Just last month while appearing on "Jimmy Kimmel Live" to promote his movie "Takers," T.I. opened up about his time behind bars.
The rapper said he mentored other inmates in an effort to get them to make smarter choices upon their releases.
"In my stay there, while I was there, I just noticed that so many cats that I was around was like, 'When I get out I don't know what I'm gonna do,' " he explained.
T.I. then said he went to the warden and proposed a class that hoped would "change criminal ways of thinking."