Guest Stars Gretchen Mol as Gillian Darmody Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder 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 Edoardo Ballerini as Ignacious D'Alessio Chris Mulkey as Boss Frank Hague Dana Ivey as Mrs. McGarry Co Starring William Hill as Ward Boss O'Neill Peter Claymore as Grey-Haired Man Enid Graham as Rose Van Alden Anna Katarina as Isabelle Jeunet Nicholas Martino as Pius D'Alessio Megan Reinking as Anabelle Barbara Tirrell as Edith Marcella Lentz-Pope as Mae Capone Mat Hostetler as Agent Keener Kylie Sanders as Ruby Jodie Sanders as Ruby Chris Cenatiempo as Bouncer Caleb Eckstein as Sonny Capone Ben Eckstein as Sonny Capone Alex Eckstein as Sonny Capone Frank Shattuck as Charlie Sheridan Faith Sandberg as Kitty Lauren Sharpe as Singer Johann Carlo as Teresina Capone Maranda Barskey as Singing Whore