May was influenced by Sam Kinison, Lenny Bruce, Buddy Hackett, and Richard Pryor. In 2003, May was chosen to participate in the first season of "Last Comic Standing". He finished in second place in the competition. 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.