Guest Stars Charlie Thurston as Roland Judith Light as Blanche Knopf Adriane Lenox as Virginia Naman Tosin Morohunfola as Isaac Danny Burstein as Stanley Lipschitz Rachel Bloom as Elaine Levitch Lindsey Broad as Dorothy Zinberg Paul Guilfoyle as Frank Bludger John Rothman as Alfred A. Knopf Sr. Quincy Tyler Bernstine as Madeline Anderson John Ellison Conlee as Evan Jones Co Starring Michael Malvesti as Benny Matthew Malone as Ralph Matthew Delamater as Lloyd Henry Lynch as TBD Michael Barra as Butcher Sam O'Byrne as Seafood Waiter Allyn Burrows as Doctor