Jackson attended West Bloomfield High School. After graduation, he moved to Los Angeles to pursue stand-up comedy and started at the Laugh Factory, 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. He hosted one episode of the Brandon T. Jackson Show on The N channel. In 2006, Jackson hosted the Up Close and Personal Tour, featuring Chris Brown, Ne-Yo, Lil Wayne, Juelz Santana and Dem Franchize Boyz. He was also a cast member on the show Wild 'N Out with Nick Cannon, and then guest-starred as a celebrity team captain for the sixth season for the show. Jackson starred in the films Tropic Thunder as Alpa Chino, Percy Jackson as Grover Underwood and Lottery Ticket as Benny. He also played 17-year-old Trent Pierce in Big Mommas: Like Father, Like Son (the sequel to Big Momma's House 2). He had a cameo in 'The Glee Project' season 2 video 'Here I Go Again' and can be seen when Maxfield gives him a flyer. In 2013, he played Axel Foley's son in an unaired pilot for a Beverly Hills Cop TV series.