Guest Stars Caroline Aaron as Shirley Maisel Will Brill as Noah Weissman Justine Lupe as Astrid Weissman Zachary Levi as Benjamin Ettenberg Brandon Uranowitz as Buzz Goldberg David Aaron Baker as Charles Connelly Nolan Gerard Funk as Josh Co Starring Connor Ratliff as Chester Jill Abramovitz as Stevie Karl Miller as Devlin Barbara Mailey as Goldie Jacob Kemp as Samuel Laura Dreyfuss as Deecy Ariana Venturi as Alya Feinberg James Lloyd Reynolds as Martin Cummings Molly Brown as Leah David Lavine as Dr. Fleischer William Geary as Around the World Dancer Allison Winn as Pearl Ester Steinberg as Sally Keith Herron as Lester Addie Weyrich as Laura Jake Silbermann as Marv Brad Heller as Phil Foster Ethan Dubin as Oliver Bentley Black as Around the World Dancer Christopher Babcock as Around the World Dancer Ian Gallagher Fitzgerald as Around the World Dancer Morgan Quinn as Around the World Dancer Taylor James Rosenberger as Around the World Dancer Amanda Mitchell as Around the World Dancer