Guest Stars Gretchen Mol as Gillian Darmody Peter McRobbie as Supervisor Frederick Elliot Erik Weiner as Agent Eric Sebso Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody Lucy Gallina as Emily Schroeder Josie Gallina as Emily Schroeder Declan McTigue as Teddy Schroeder Rory McTigue as Teddy Schroeder Victor Verhaeghe as Damien Fleming Robert Clohessy as Alderman Jim Neary Adam Mucci as Deputy Halloran William Hill as Alderman George O'Neill Enid Graham as Rose Van Alden Stephen DeRosa as Eddie Cantor Anna Katarina as Isabelle Jeunet Nicholas Martino as Pius D'Alessio Lisa Joyce as Mary Dittrich Josiah Early as Robert Dittrich Jordan Gelber as Simon Barbara Tirrell as Edith Charleigh Parker as Lady Jean Sarah Skogland as Dancer Kenneth Tigar as Dentist Katie Henney as Young Woman Mark Lotito as Dr. Cuomo Dan Daily as Buck Douglas Ryan as Conductor Elizabeth Rose Sharp as German Child Fred Armstrong as Player #2 Joe Iacona as Elderly Patient Stephen Badalamenti as Player #1 Tuck Milligan as Dr. Brubaker Vic Noto as Hearse Clayton James Mackay as Boy Michele Tauber as Mrs. Fishbaum John Marinacci as Dealer