Guest Stars Gretchen Mol as Gillian Darmody Jack Huston as Richard Harrow Anatol Yusef as Meyer Lansky Lucy Gallina as Emily Schroeder Rory McTigue as Teddy Schroeder Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Greg Antonacci as Johnny Torrio Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Peter McRobbie as Supervisor Elliot Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Chris Mulkey as Boss Frank Hague 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 Rony Clanton as Langston Peter Claymore as Grey-Haired Man Kevin Henderson as Dr. Carl Surran Enid Graham as Rose Van Alden Stephen DeRosa as Eddie Cantor Johnnie Mae as Louanne Nicholas Martino as Pius D'Alessio Samuel Taylor as Paddy Ryan Megan Reinking as Anabelle Virginia Kull as Nan Britton Felicity Stiverson as Babette's Dancer Mark Manley as Babette's Dancer William Ward as Babette's Dancer Tracy Sallows as Katheryn Bader Allen Lewis Rickman as George Baxter Eric Schneider as Sixtus D'alessio Noah Racey as Babette's Dancer Doug Sheppard as Babette's Dancer Susan Wands as Mrs. O'Neil Fiana Toibin as Mrs. Neary Kenn Mann as Postal Worker Mat Hostetler as Agent Keener Vince Giordano as Bandleader Danielle Davenport as Chalky's Date Adam Zotovich as Babette's Dancer Amanda Suchy as Babette's Dancer Craig Geraghty as Voter #1 Galway McCullough as Voter #2 Gary Littman as Radio Announcer Remy Bennett as Floozy