Guest Stars Kevin Pollak as Moishe Maisel Caroline Aaron as Shirley Maisel Joel Johnstone as Archie Cleary Bailey De Young as Imogene Cleary Brian Tarantina as Jackie Erin Darke as Mary Wallace Shawn as Herb Smith Co Starring Matteo Pascale as Ethan Nunzio Pascale as Ethan Matilda Szydagis as Zelda Holly Curran as Penny Pann Jack O'Connell as Jerry Peggy J. Scott as Verla Lilli Stein as Vivian Wakeema Hollis as Harriet Joanna Glushak as Mrs. O'Toole Frank Ridley as Sal Zac Jaffee as Passerby Dave T. Koenig as Darren Erin West as Affluent Woman #2 Mike Rosengarten as Banjo Player Allison Rogers as Affluent Woman #1 Jeremiah Wiggins as Mr. Stanyon Brian Berrebbi as Ronny Elizabeth Loyacano as Woman in Chair Phillip James Brannon as Customer Carly Zien as Young Housewife Kara Jackson as Mrs. Stapleton Ethan Lipton as Ethan Carter Dillon Geyselaers as Heckler Noah Gaynor as Arnie