He started with improvisational comedy in Soup Kitchen Saloon. He came into show business with a comedy troupe named as “The Second City”. He got a spot in “Saturday Night Live” in the year 1991. He was a cast member for a long time and appeared until the year 2000. He had a record of staying in the show for longest time i.e. 10 years, which was broken by Darrel Hammond in the year 2005. He was known for spoofing the celebrities in the show like Michael Jackson, Oprah Winfrey, Tiger Woods, Erykah Badu and O.J. Simpson. He got an original character with Leon Phelps, who was named “The Ladies man” and a host talk show. The character was revised in the movie “The Ladies man” in the year 2000. This portrayed the character’s aspiration to find love and a suitable place for his program on radio. The movie did not perform well and fail to impress the critics.

He had also made a guest appearance in Saturday Night Live for promotion of the movie. It became classic on TV and DVDs. He was seen in the movie “The Three Days” in the year 2001. He was seen in the role of Miles McDermott in the movie “The Even Stevens Movie” in the year 2003. He bagged a regular role in “The Michael Richards Show” which was a sitcom and aired for a short time on NBC. In 2004, he was seen in supporting role in the movie “The Cookout”. He made a guest appearance as a client in an episode of the second season of the comedy show “The Office”. He was seen in the role of Principal in the movie “Mean Girls”. This movie was written by another cast member of Saturday Night Live. He was part of an album named as “White People”. He had a supporting role in the movie “Walk Hard: The Dewey Cox Story” in the year 2007. He was also seen in movies: “Wayne’s World 2”, “Coneheads” and “Its Pat”. These movies were based on different characters on Saturday Night Live. In 2006, he was seen in the movie “The Benchwarmers”. He appeared as comic field reporter in “The Late Late show with Craig Ferguson”. He was seen as a co-star in “Marry Me” which was a short lived show on NBC. He still performs in improvisational comedy shows in Chicago and Los Angeles.

He married his long-time girlfriend Michelle Taylor in the year 1997. However the couple started having problems in their relationship and hence the couple headed for divorce in the year 2005. His biography can be found on sites like Wikipedia and IMDb. He is active on Twitter and he always tweets for his fans. His estimated net worth is $3 million.