Guest Stars Gretchen Mol as Gillian Darmody Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Erik Weiner as Agent Sebso Peter McRobbie as Supervisor Elliot Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss O'Neill Adam Mucci as Deputy Halloran Enid Graham as Rose Van Alden Stephen DeRosa as Eddie Cantor Nicholas Martino as Pius D'Alessio Anna Katarina as Isabelle Jeunet Lisa Joyce as Mary Dittrich Josiah Early as Robert Dittrich Jordan Gelber as Simon Charleigh Parker as Lady Jean Barbara Tirrell as Edith Mark Lotito as Dr. Cuomo Katie Henney as Young Woman 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