His first acting role came when he went to Atlanta, Georgia to appear as an extra in a commercial, which turned into a feature part. He appeared in a music video for the band Little Texas. Lester moved to Los Angeles and began doing stand-up comedy in comedy clubs. His first film role was in the movie Good Burger in 1997, and two years later he had a recurring role on the TV comedy Freaks and Geeks. He also appeared in Not Another Teen Movie, which parodied his role in Varsity Blues.