Special Guest Stars Jeannie Berlin as Ruth Heidelbaum Guest Stars Jonno Davies as Tobias Henry Hunter Hall as Cheeks Johnson Ebony Obsidian as Carol Lockhart Annie Hägg as Young Ruth Zack Schor as Young Meyer James Le Gros as Chief Harry Grimsby Caleb Emery as Arthur "Bootyhole" McGuigan Kenneth Tigar as Heinz Richter Jason Kravits as Rabbi Grossman Victor Williams as Detective Kennedy Groton Tramell Tillman as Detective Sommers Leigh Ann Larkin as Lottie Simpson Izabella Miko as Helen Hirsch Gordon Winarick as Dennis Duncan Veronika Nowag-Jones as Gretel Fischer Co Starring Cassidy Layton as Chava Apfelbaum James Rutledge as Edward / Butler Danny Doherty as Meyer's Driver Judy Rosenblatt as Mrs. Schlosstein David Sitler as King Lear Man Allison Wick as Chess Board Prisoner #8 Audrey Bennett as Trinity Simpson Manny Galan as Hell Devils Leader Kyle Leibovitch as Chess Board Prisoner #14 Zack Segel as Surly Waiter Anna Podolak as Angry Woman Ryan Welsh as Chess Board Prisoner #15 Calvin Knie as Young Heinz Richter Riley Galt as Chess Board Prisoner #9 Chloe Ava Bryan as Girl in Laundromat Sophia Gonzalez as Little Girl in Toy Shop Inna Yesilevskaya as Wailing Woman Mick Diflo as Skeezy Man Paul Grossman as Chess Board Prisoner #4 John Basedow as News Anchor #1 Brandon Elia as Rookie Cop Holly Grum as Chess Board Knight Ari Tomais as Chess Board Bishop Markus McClain as Chess Board Prisoner #2 Sara Tepper as Chess Board Prisoner #13 Alison Maddren as Chess Board Prisoner #12 Lesley Noyes as Chess Board Prisoner #3 Richard Ruskin as Chess Board Prisoner #6 Max MacKenzie as Markus Roth T. Ryder Smith as Ulysses F. O'Harrison Logan Crawford as News Anchor #2 Tracie Higgins as Judy Brown Karen Chmielnicki as Chess Board Prisoner #5 Bill Timoney as Congresman Marshall Vince Eisenson as Chess Board Prisoner #1 Joshua Alscher as Chess Board Prisoner #11 Musto Pelinkovicci as Rebbe Apfelbaum Jaxon Bartok as Sawyer Simpson Stephen D'Ambrose as Nasa Suit #1 Frank Bal as Terry Stephen Pilkington as Carl Hirsch Jack Sochet as Chess Board Prisoner #7 Julianna Pitt as Chess Board Prisoner #10 Andrew Rogers as Joe Brown Marc Schottner as Nazi Administrator Jeremy Lanuti as Biff Jr. Ava Eisenson as Lost Woman Brandon Engman as Teen Clerk