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.

[1] 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.

[1] 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.

"[2] He was given the role of Harland Osbourne, the Harvard University liaison who receives the Wiley College debate team.

[2] Leak and his older sister Liberty were named for their father's love of the criminal justice system.