Guest Stars 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 Peter McRobbie as Supervisor Elliot Stephen DeRosa as Eddie Cantor Pearce Bunting as Bill McCoy Johnnie Mae as Louanne Danny Burstein as Lolly Steinman Dana Ivey as Mrs. McGarry Joseph Sikora as Hans Schroeder Frank Crudele as Big Jim Colosimo Billy Smith as Davey Murdoch 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 Tracy Middendorf as Babette John Rue as Mayor Harry Bacharach Samuel Taylor as Paddy Ryan Joseph Riccobene as Frankie Yale Nic Novicki as Carl Heely Jordan Gelber as Simon Kevin Carolan as Boardwalk Barker Chase Coleman as Billy Winslow Charleigh Parker as Lady Jean John Mainieri as Hotel Manager Vince Giordano as Bandleader Steve Witting as Funeral Director George R. Sheffey as Traymore Hotel Concierge Allen Jared as Crying Husband Jeanette Gould as Funeral Attendee Loyita Chapel as Crying Wife Noel Wilson as Ward Boss Prudence Wright-Holmes as Widow Randy Neumann as Referee Scott Jaeck as Ward Boss Jonathan Brody as Reporter