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 Tom Aldredge as Ethan Thompson Dana Ivey as Mrs. McGarry Emily Meade as Pearl Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss O'Neill Edward McGinty as Alderman Al Boyd Nisi Sturgis as June Thompson Pearce Bunting as Bill McCoy David Aaron Baker as Bill Fallon John Rue as Mayor Harry Bacharach Nic Novicki as Carl Heely Susan Varon as Madam Regina Steven L. Barron as Vocal Reporter Faith Sandberg as Kitty Susan Blommaert as Irene Davis Mark Povinelli as Kevin Kiley John Keating as Celt #4 Edelen McWilliams as Bettyanne Mulhaney Margot Jewers as Temperance Singer Jack O'Connell as Celt #3 Mikey Post as Mike Green Nicole Lackey as Temperance Singer Raymond McAnally as Workman #1 Sean Allison as Boxer #1 Christopher J. Quinn as Reporter #2 Judson Jones as John #1 Lynne Valley as Temperance Singer Laurence Lowry as Celt #2 Kenneth Cavett as Drunken Celt John Treacy Egan as Duncan O'Connor John Joseph Gallagher as Celt #1 Fran Lieu as Temperance Singer Erin Mae Miller as Temperance Singer Cezary Skarzynski as Boxer #2 Austin Jones as Waiter Martin Anna Stone as Bridget Walsh