Guest Stars Gretchen Mol as Gillian Darmody Anatol Yusef as Meyer Lansky Kevin O'Rourke as Mayor Edward Bader Erik Weiner as Agent Sebso Peter McRobbie as Supervisor Elliot 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 Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss 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 John Rue as Mayor Harry Bacharach Al Linea as Matteo D'Allessio 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