After obtaining his degree from Auburn University, Leak relocated to Atlanta, Georgia. He was signed to an agency which landed him a number of roles in commercials (such as for Verizon Wireless), television shows and independent films. He appeared in films such as Bobby Jones: Stroke of Genius, The Cure and Watermelon Honey, and television shows such as K-Ville, Moonlight and Women's Murder Club, which he described as his "training ground" for becoming a professional actor. His agent sent Leak's résumé to the producers of The Great Debaters. When he met Denzel Washington, the Director and also an actor in The Great Debaters, in a follow-up callback audition, Leak says "It was one of those moments. I knew my life was about to change." He was given the role of Harland Osbourne, the Harvard University liaison who receives the Wiley College debate team. When he accepted the role in May 2007, he ended his acting stint on Atlanta's longest-running play, Peachtree Battle.