Guest Stars Gretchen Mol as Gillian Darmody Jack Huston as Richard Harrow Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Erik Weiner as Agent Sebso Lisa Joyce as Mary Dittrich Tom Aldredge as Ethan Thompson Josiah Early as Robert Dittrich Michael Badalucco as Harry Prince Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss O'Neill Adam Mucci as Deputy Halloran Edward McGinty as Alderman Al Boyd Kevin Henderson as Dr. Carl Surran Johnnie Mae as Louanne David Aaron Baker as Bill Fallon Megan Reinking as Anabelle Franklin Ojeda Smith as Deacon Lemuel Cuffy Charleigh Parker as Lady Jean Bill Buell as Donald Flance Remy Auberjonois as Theodore Hardeen Karen Walsh as Mrs. Boyd