May graduated from the High School for the Performing and Visual Arts in Houston. He finished in second place in the competition, with Dat Phan winning first place.
Kinison suggested that May move to Houston, Texas to further develop his comedy routine. He then moved to Los Angeles to pursue a career in entertainment. In 2003, May was chosen to participate in the first season of Last Comic Standing.
After that, he appeared in comedy shows like The Wayne Brady Show and The Tonight Show with Jay Leno.
In 2005, he was the only white comedian on The Big Black Comedy Show, which also featured Mo"Nique, Rodman, and Vince Morris. In 2005, May released his comedy album, Just Correct.
Since then, he has recorded four Comedy Central specials: Girth of a Nation (2006), Prime Cut (2007), Austin-tatious (2008), and Too Big To Ignore (2012), as well as two Netflix specials, Unruly (2015) and Imperfectly Yours (2015). He appeared in the movie Foreign Da Love of Money.
He also performed at the "Gathering of the Juggalos 2012.".