His dulcet tenor voice and suave appeal landed him a continuing featured role on "Living Single" where he played "Tripp" during the hit sitcom's final year. And he also played "Johnnie" on "The Parkers" in the final season's run.

In 2003 he accompanied platinum recording Canadian chanteuse Deborah Cox to starred in a stage play "Love on Lay-Away," written by David E. Talbert whom offers a fly-on-the-wall look at the lives of three very different couples. In the play Jackson stars in the role of Anthony a witty salesman whose ability to commit falls short. He also appeared in the 2005 hit stage play "Friends and Lovers" based on the bestselling Eric Jerome Dickey novel, playing the role of Richard. Another notable role he played was in "Issues: We've all got 'em" (2006).