During his school years, Chott appeared in numerous plays and musicals. He graduated from Ritenour High School, and has since been inducted into their Alumni Hall of Fame. He continued pursuing theater in college at Central Methodist University in Fayette, Missouri, acting in a wide variety of plays. He was also in Chi Delta fraternity while at Central Methodist. He left Missouri in 1992, and headed to Chicago, IL where he quickly became involved with improvisational theater at ComedySportz, IO Theater, and the Second City comedy troupe. His contemporaries in the Chicago improv scene included Steve Carell, Stephen Colbert, Tina Fey and Amy Poehler.
Chott toured the country with the Second City, and in 1995 he made his television debut on The Dana Carvey Show, among a repertory cast that included Stephen Colbert, Steve Carell, and Robert Smigel. His most lasting contribution to the program was as the announcer for The Ambiguously Gay Duo, a series of animated shorts created by Smigel and J.J. Sedelmaier, which continued to be produced by J.J. Sedelmaier Productions for Saturday Night Live after the quick cancellation of "The Dana Carvey Show."
