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For better or for worse, T.I. also courted a good deal of controversy during his rise to superstar status. Far more ink was spent on his legal issues and conflicts with other rappers, including fellow Southerner Lil' Flip, than on his Katrina relief efforts and other humanitarian involvements. One notable event occurred on May 3, 2006, when T.I.'s crew was caught up in a shooting after a show in Cincinnati. The crossfire left three people injured, while longtime friend and personal assistant Philant Johnson was fatally wounded. Despite such incidents, T.I. continued to flourish as the decade drew to a close, releasing three chart-topping rap singles and four Top Five pop hits between 2008 and 2009. His career took a breather in 2009, however, when the rapper entered an Arkansas prison to serve a year-long sentence related to federal gun charges. He was released from prison at the end of 2009, serving the rest of his sentence at a halfway house in Atlanta.
Just prior to the December 2010 release of his seventh album, No Mercy, he returned to prison, sentenced to 11 months for violating his probation. The album went gold, and the rapper was nominated for two Grammy Awards. After his release, he continued recording and co-starred in the VH1 series T.I. and Tiny: The Family Hustle. He issued Trouble Man: Heavy Is the Head, in December 2012. Influenced by Pharrell Williams, the rapper moved to the Columbia family of labels in 2013. Williams also executive produced his 2014 effort Paperwork, an album introduced by the single "About the Money" featuring Young Thug. It was T.I.'s eighth consecutive Top Ten album.
In 2015, after appearances in a handful of films, including Entourage and Ant-Man, he returned as TIP with the five-track EP Da' Nic. Parting ways with Columbia soon after, he signed a deal with Jay-Z's Roc Nation in early 2016. His first output for the label arrived with the EP Us or Else. Supporting the Black Lives Matter movement, the politically charged collection presented an unflinching look at race and power in America. An extended version titled Us or Else: Letter to the System arrived at the end of the year. In 2018, T.I. recruited Yo Gotti for "Wraith" and Meek Mill for "Jefe," a pair of singles from his long-awaited tenth set, The Dime Trap. Further guests on the effort included Jeezy ("More & More"), Anderson .Paak ("At Least I Know"), Young Thug ("The Weekend"), and more, as well as producers Scott Storch, Just Blaze, Swizz Beatz, and others. Upon release, the album debuted at number 13 on the Billboard 200 and rose into the R&B/Hip-Hop Top Ten. ~ Andy Kellman