Guest Stars Robert Morse as Bertram Cooper Alison Brie as Trudy Campbell Mark Moses as Herman "Duck" Phillips Anne Dudek as Francine Hanson Andy Umberger as Dr. Arnold Wayne Joe O'Connor as Tom Vogel Sheila Shaw as Jeannie Vogel Katherine Boecher as Annie Gregory Wagrowski as Dr. Oliver James Keane as Night Manager Co Starring Kiernan Shipka as Sally Draper Deborah Lacey as Carla Aaron Hart as Robert Draper Marten Holden Weiner as Glen Bishop Maura Soden as Nurse Wilson Mandy McMillian as Rita Jonathan Spencer as Victor Manny Ross Mackenzie as Joe Harriman Lisa Lupu as Janet Richard Willgrubs as Lynn Taylor