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