Guest Stars Kevin Pollak as Moishe Maisel Joel Johnstone as Archie Cleary Bailey De Young as Imogene Cleary Luke Kirby as Lenny Bruce David Paymer as Harry Drake Max Casella as Michael Kessler Joe Grifasi as Judge Hackett Co Starring Nunzio Pascale as Ethan Matteo Pascale as Ethan Matilda Szydagis as Zelda Cynthia Darlow as Mrs. Moskowitz Chris Chirdon as Don Gina Costigan as Officer Judy Adriana DeMeo as Trish Amanda Bruton as Vicki Ato Blankson-Wood as Lindsey Trent Borris York as Soundman Diallo A. House as Bass Player Stacy Dillard as Sax Player Ismail Lawal as Drummer Joey Stromberg as Palmer Witherspoon Chris Carfizzi as Ben David Mason as Mr. Cranmer Randall McNeal as Kenneth Steve Hamm as Court Officer