Guest Stars Kevin Pollak as Moishe Maisel Caroline Aaron as Shirley Maisel Bailey De Young as Imogene Cleary Brian Tarantina as Jackie Jane Lynch as Sophie Lennon David Paymer as Harry Drake Katrina Lenk as Cosma Zach Appelman as David Blumenthal Co Starring Matilda Szydagis as Zelda Cynthia Darlow as Mrs. Moskowitz Steven Hauck as Dawes Bern Cohen as Rabbi Krinsky Adam B. Shapiro as Cantor Simon Feil as Curtis Bill Coelius as Lawrence Ned Van Zandt as Doug David Little as Chaim Lenny Palmieri as 13-Year-Old Joel Jaxon Folds as 10-Year-Old Boy David Scott Purdy as Man Stephanie Gould as Linda