Guest Stars Anatol Yusef as Meyer Lansky Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Kevin O'Rourke as Mayor Edward Bader Greg Antonacci as Johnny Torrio Glenn Fleshler as George Remus Christopher McDonald as Harry Daugherty William Forsythe as Manny Horvitz Meg Steedle as Billie Kent Patrick Kennedy as Dr. Douglas Mason Stephen DeRosa as Eddie Cantor Michael Cumpsty as Father Brennan Arron Shiver as Dean O'Banion Lucas Caleb Rooney as Joe Miller Co Starring Connor Noon as Tommy Darmody Edward McGinty as Alderman Al Boyd Jacqueline Pennewill as Lillian Rony Clanton as Langston Christiane Seidel as Sigrid Ed Jewett as Jess Smith Matt Hobby as Phillip Emily Dorsch as Cornelia Predock Kerry O'Malley as Edwina Shearer Nick Wyman as Dr. Landau Joseph Riccobene as Frankie Yale William Ward as Babette's Dancer John Harrington Bland as Scotty Gulliver Joseph Caniano as Jake Guzik Mark Manley as Babette's Dancer Felicity Stiverson as Babette's Dancer Mike Houston as Ralph Jenna Gavigan as Evelyn Kevin Carolan as Boardwalk Barker Ned Noyes as Hank Ryan Woodle as Phil Paul Locke as Rosetti thug #1 Robin Madel as Prudence Tyler Ingram as Babette's Dancer Charlotte Maier as Mrs. Landau Erin Fogel as Mary Steven Hauck as Mr. Pendergast Suzanne Savoy as Mrs. Pendergast Yelena Shmulenson as Emma Horvitz Robin Hopkins as Housewife Robert C. Kirk as Mr. Johansen Richard Flight as Rosetti thug #5 Nick Stannard as Board dignitary #1 Margaret Daly as Greedy Party Guest Manuel Palazzo as Party Dancer Lee Zarrett as Nate Kiva Dawson as Party Dancer Kate Cullen Roberts as Gossipy Prostitute John Mondin as Carny James Rutledge as Hospital chairman Jacob Clemente as Delivery Boy Deanna Dys as Party Dancer Carolyn Doherty as Party Dancer Anthony Devito as Deuces Bouncer #1 Matthew Lawler as Mr. Posner