Guest Stars Joel Johnstone as Archie Cleary Bailey De Young as Imogene Cleary Brian Tarantina as Jackie Luke Kirby as Lenny Bruce Cynthia Darlow as Mrs. Moskowitz Jane Lynch as Sophie Lennon LeRoy McClain as Shy Baldwin Zachary Levi as Benjamin Ettenberg Max Casella as Michael Kessler David Aaron Baker as Charles Connelly Christopher Fitzgerald as Bobby Katrina Lenk as Cosma Co Starring Matteo Pascale as Ethan Nunzio Pascale as Ethan Steven Hauck as Dawes Karl Miller as Devlin James Lloyd Reynolds as Martin Cummings Andrew Keenan-Bolger as Perry Cadden Jones as Secretary Roy Farfel as Male Driver #2 Dave Konig as Comic Nikka Graff Lanzarone as Myrna Blaise Corrigan as Male Driver #1 Alicia Olatuja as Girl #1 Gabrielle Elisabeth as Girl #2 Yasmeen Sulieman as Girl #3 Ted Sperling as Steve Allen Uncredited Bob Leszczak as Maisel and Roth Supervisor