 Olson and comedian Lenny Clarke became roommates in Harvard Square; comedians from all over the country stayed with them while performing in Boston comedy clubs.Olson wrote for Clarke, who was the most popular comedian in Boston.Their apartment became known as The Barracks, a legendary hub of comedy and depravity that was the subject of a television special on Boston comedy in the 1980s, and also of the award-winning documentary on the Boston comedy scene "When Standup Stood Out" (2006) directed by filmmaker-comedian Fran Solomita.