[1][2] His maternal grandfather, Royal Titus Bozeman, was a Pentecostal child preacher named a "Boy Wonder" by Indiana newspapers.

[5] After graduation, he moved to Los Angeles to pursue stand-up comedy and started at the Laugh Factory,[6] as well as opened for Wayne Brady and Chris Tucker.

His role as Junior in the film Roll Bounce won him the 2006 Black Reel Award for Breakthrough Performance.

In 2006, Jackson hosted the Up Close and Personal Tour, featuring Chris Brown, Ne-Yo, Lil Wayne, Juelz Santana and Dem Franchize Boyz.

In 2013, he played Axel Foley's son in an unaired pilot for a Beverly Hills Cop TV series.