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 Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Geoff Pierson as Senator Walter Edge Chris Mulkey as Boss Frank Hague Emily Meade as Pearl 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 Anna Katarina as Isabelle Jeunet John Rue as Mayor Harry Bacharach Al Linea as Matteo D'Allessio William Ward as Babette's Dancer Mark Manley as Babette's Dancer Felicity Stiverson as Babette's Dancer Barbara Tirrell as Edith Susan Varon as Madam Regina Jennifer Bowles as Babette's Dancer Sean Weil as Liam Dieter Riesle as Babette's Dancer Frank Root as Babette's Dancer Frank Shattuck as Charlie Sheridan Nathan Williams as Harvey Tyler Ingram as Babette's Dancer Demosthenes Chrysan as George Anastos Alison Solomon as Babette's Dancer Cat Davis as Commodore's Whore Derek Milhem as Attendant Erin McGrath as Edith Day Jeffrey C. Wolf as Babette's Dancer Jimmie James as Klansman #1 John Lantz as Taylor Meredith Riley Stewart as Babette's Dancer Nikolas Kontomanolis as Chicago Patron Simone Assboeck as Babette's Dancer Scott Sowers as Joseph Earl Dinler