Guest Stars Gretchen Mol as Gillian Darmody Jack Huston as Richard Harrow Anatol Yusef as Meyer Lansky Greg Antonacci as Johnny Torrio Peter McRobbie as Supervisor Frederick Elliot Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Chris Mulkey as Boss Frank Hague Co Starring Brady Noon as Tommy Darmody Connor Noon as Tommy Darmody Josie Gallina as Emily Schroeder Lucy Gallina as Emily Schroeder Rory McTigue as Teddy Schroeder Declan McTigue as Teddy Schroeder Kevin O'Rourke as Mayor Edward Bader Victor Verhaeghe as Damien Fleming Robert Clohessy as Alderman Jim Neary William Hill as Alderman George 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 Allen Lewis Rickman as George Baxter Felicity Stiverson as Babette's Dancer Mark Manley as Babette's Dancer William Ward as Babette's Dancer Tracy Sallows as Katheryn Bader Fiana Toibin as Mrs. Neary Eric Schneider as Sixtus D'alessio Noah Racey as Babette's Dancer Doug Sheppard as Babette's Dancer Susan Wands as Mrs. O'Neil Kenn Mann as Postal Worker Mat Hostetler as Agent Keener Vince Giordano as Bandleader Gary Littman as Radio Announcer 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 Remy Bennett as Floozy
