Lester was born in Kennesaw, Georgia.[citation needed]
Lester's 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. In 1999 Lester played the role of Billy Bob in the film Varsity Blues, which would become the role he is most known for. That year he also had recurring roles on two TV drama comedies, Freaks and Geeks and Popular. He also appeared in Not Another Teen Movie, portraying a character that was a parody of his role in Varsity Blues.

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