He was the most famous "saloon comic" in Boston during the 1980s, the heyday of the Boston comedy scene. 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. In 1980, Clarke wrote and starred in a local television show Lenny Clarke's Late Show featuring Wright and Leary, in collaboration with Boston comedy writer Martin Olson] 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.
