Guest Stars Caroline Aaron as Shirley Maisel Luke Kirby as Lenny Bruce Will Brill as Noah Weissman Justine Lupe as Astrid Weissman Zachary Levi as Benjamin Ettenberg Brandon Uranowitz as Buzz Goldberg Bryan Batt as Dr. Stone Danny Burstein as Sewell Laura Osnes as Lizzie Bobby Steggert as Phipps Co Starring Andrew Polk as Fred Peggy J. Scott as Verla Connor Ratliff as Chester Joanna Glushak as Mrs. O'Toole Jill Abramovitz as Stevie Barbara Mailey as Goldie Jacob Kemp as Samuel Arielle Goldman as Eliana Allison Strong as Talia Goldstein Christopher Manning as Kent Cheryl Stern as Ida Lauren Blumenfeld as Gabi John Weigand as Mel Stephanie Rothenberg as Ruthie Lee Wilkof as Melvin Ben Graney as Robbie Rick Crom as Jerome Peter Linari as Zundee Annie Meisels as Operator Joseph LaRocca as Howie Misha Brooks as Bellhop #1 Tony Macht as Bellhop #2 Chara Kirkland as Cocktail Waitress Armand Reiser as Kitter