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 Greg Antonacci as Johnny Torrio Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Erik Weiner as Agent Sebso Peter McRobbie as Supervisor Elliot Danny Burstein as Lolly Steinman Frank Crudele as Big Jim Colosimo Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody Edward McGinty as Alderman Al Boyd Peter Claymore as Grey-Haired Man Johnnie Mae as Louanne Julian Rozzell Jr. as Harlan Joseph Riccobene as Frankie Yale Nic Novicki as Carl Heely Jordan Gelber as Simon Allen Lewis Rickman as George Baxter Megan Ferguson as Claudia Bob Sorenson as Dale Lauren Champlin as Female Patient Kendel Ridgeway as Nurse Sam Guncler as Croupier Michael Warner as Klan Recruiter Ken Forman as Stage Manager Brent Bateman as Eddie Corrigan Bob Engel as Abe Klein Annie Paul as Showgirl #1 Allison Guinn as Capone's Whore Clem Cheung as Chinese Man