Guest Stars Gretchen Mol as Gillian Darmody Anatol Yusef as Meyer Lansky Peter McRobbie as Supervisor Frederick Elliot Erik Weiner as Agent Eric Sebso Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Lisa Joyce as Mary Dittrich Danny Burstein as Lolly Steinman Josiah Early as Robert Dittrich Co Starring Brady Noon as Tommy Darmody Connor Noon as Tommy Darmody Kevin O'Rourke as Mayor Edward Bader William Hill as Alderman George O'Neill Adam Mucci as Deputy Halloran Tracy Middendorf as Babette Johnnie Mae as Louanne Anna Katarina as Isabelle Jeunet Nicholas Martino as Pius D'Alessio Al Linea as Matteo D'Allessio John Rue as Mayor Harry Bacharach Virginia Kull as Nan Britton Tracy Sallows as Katheryn Bader Chase Coleman as Billy Winslow Louis Vanaria as Lucien D'Alessio Eric Schneider as Sixtus D'alessio Henry Stram as D.W. Fletcher Karen Chmielnicki as Maryska Kathy Brier as Sophie Tucker Shane Tunney as Local Spelman Beaubrun as Zulu Warrior Don Stitt as Boardwalk Barker
