In the beginning Oakerson worked as a chauffeur/bouncer for strippers and as a children’s party entertainer to make ends meet. He has opened for Dave Attell and toured with Korn before touring as a headliner. He co-hosted Movies on Tap on Spike TV. He played Neil on the series Z Rock and appeared in the first episode of season 1 of Louie and episode 6 of season 3. His television credits include Comedy Central’s Premium Blend,Comedy Central Presents and Tough Crowd with Colin Quinn, along with multiple appearances on BET’s Comic View and HBO’s P. Diddy’s Bad Boys of Comedy.