[5] The DVD release When Standup Stood Out (2006) details Clarke's early career and affiliations with other famous Boston comics, such as Steven Wright and Denis Leary, his good friends.

[6] Clarke and Olson were roommates, and their apartment, known by comedians as "The Barracks", was a notorious "crash pad" for comics visiting Boston, per the film.

[citation needed] It was on this show that he announced he would be a regular on the 2009 Fox sitcom Brothers as the racist neighbor who is married to a black woman.

[citation needed] In the 2011-12 TV season, he landed a role as the main character's father on the NBC mid-season replacement sitcom Are You There, Chelsea?.

[citation needed] On the evening of January 19, 2010, Clarke appeared on stage at the victory speech of Republican Senator-elect from Massachusetts Scott Brown, who was elected to the U.S. Senate seat formerly held by Ted Kennedy.