 Olson's friends Paul Barclay and Bil Downes started the first comedy club in Boston in 1977.There Olson became house piano player and performed as a comedian with an absurdist deadpan act, playing the guitar and hosting other comedians as his eccentric guests.Olson worked for and wrote with the comedians who became his friends – Sean Morey, Lenny Clarke, Bobcat Goldthwait, Joe Alaskey, Don Gavin, Barry Crimmins, Steven Wright, Jimmy Tingle, Denis Leary, Steve Sweeney, Kevin Meaney, Kevin Nealon, Kevin Rooney, and many other Kevins.