Guest Stars Anatol Yusef as Meyer Lansky Kevin O'Rourke as Mayor Edward Bader Victor Verhaeghe as Damien Fleming Julianne Nicholson as Esther Randolph Ivo Nandi as Joe Masseria Glenn Fleshler as George Remus Meg Steedle as Billie Kent Nick Sandow as Waxey Gordon Co Starring Brady Noon as Tommy Darmody Josie Gallina as Emily Schroeder Lucy Gallina as Emily Schroeder Connor Noon as Tommy Darmody Declan McTigue as Teddy Schroeder Rory McTigue as Teddy Schroeder Nisi Sturgis as June Thompson Chris Caldovino as Tonino Sandrelli Brandon Zumsteg as Brian Thompson Wrenn Schmidt as Julia Sagorsky Kevin Henderson as Dr. Carl Surran Curt Bouril as Clifford Lathrop Joseph Riccobene as Frankie Yale Marc D. Donovan as Sheriff Ramsey Jack Ferry as Gareth Murray Kate Loprest as Corrine Jenna Gavigan as Evelyn Jim Schubin as Phil Gardner Kate Harpootlian as Dancer KC Wright as Josephine Clem McIntosh as Wellman Bryant Carroll as "Wild Bill" Lovett Janet Anderson as Bible Camp Lady Stephanie Mas as Dancer Tommaso Antico as Dancer Susan Barnes Walker as Tabor Heights Librarian Rhett Henckel as Treasury Agent Morgan S. Smith as Wellman's date Michaela Sprague as Dancer Lindsay Roebuck as Dancer John Alix as Dancer Danielle Froelich as Dancer Colby Lindeman as Dancer Clifton Samuels as Dancer Christopher Cangero as Dancer Patrick Carroll as Peg Leg Lonergan