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 Adam Mucci as Deputy Halloran William Hill as Ward Boss O'Neill Edward McGinty as Alderman Al Boyd Kevin Henderson as Dr. Carl Surran David Aaron Baker as Bill Fallon Johnnie Mae as Louanne Megan Reinking as Anabelle Franklin Ojeda Smith as Deacon Lemuel Cuffy Charleigh Parker as Lady Jean Remy Auberjonois as Theodore Hardeen Bill Buell as Donald Flance Karen Walsh as Mrs. Boyd