Roundtree began his early training as an actor by joining drama clubs in his native hometown, Augusta, Georgia.
He began his formal training as an actor at the Augusta Mini Theatre under the direction of Tyrone Butler and Judith Simon-Butler.
While still attending college, Roundtree made his screen debut in the movie Drumline, starring Nick Cannon, Orlando Jones and Zoe Saldana.
That movie, which was released in 2002, along with a television commercial appearance, qualified him to be a member of the Screen Actors Guild.
After attending college for three years at Clark Atlanta University, Roundtree decided to pursue his acting career full-time.