Special Guest Stars John Slattery as Roger Sterling Guest Stars Joel Murray as Fred Rumsen Talia Balsam as Mona Sterling Elizabeth Rice as Margaret Sterling Rosemarie DeWitt as Midge Daniels Ian Bohen as Roy Hazelitt Rebecca Creskoff as Barbara Katz Irene Roseen as Lily Meyer Co Starring Kiernan Shipka as Sally Draper Alexa Alemanni as Allison Brynn Horrocks as Abigail Whitman Brandon Killham as Dick Morgan Rusler as Mack Johnson Maxwell Huckabee as Robert Draper Sarah Jannett Parish as Donna Hrach Titizian as Hungarian Man Bruno Oliver as Nick Rodis Jennifer Fitzgerald as Judy Heather Fox as Ginger George Anthony Alvarez as Waiter Gordana Rashovich as Dr. Gretta Guttman Megan Duffy as Poetry Girl Danny Jacobs as Yoram Ben Shulhai