Jon Hamm Don Draper Actor John Slattery Roger Sterling Actor Rich Sommer Harry Crane Actor Bryan Batt Salvatore Romano Actor Vincent Kartheiser Pete Campbell Actor Christina Hendricks Joan Holloway Actor January Jones Betty Draper Actor Elisabeth Moss Peggy Olson Actor Rosemarie DeWitt Midge Daniels Actor Maggie Siff Rachel Menken Actor Aaron Staton Ken Cosgrove Actor Michael Gladis Paul Kinsey Actor Robert Morse Bertram Cooper Guest Star Anne Dudek Francine Hanson Guest Star Katherine Boecher Annie Guest Star Alison Brie Trudy Campbell Guest Star James Keane Night Manager Guest Star Mark Moses Herman "Duck" Phillips Guest Star Joe O'Connor Tom Vogel Guest Star Sheila Shaw Jeannie Vogel Guest Star Andy Umberger Dr. Arnold Wayne Guest Star Gregory Wagrowski Dr. Oliver Guest Star Aaron Hart Robert Draper Guest Star Deborah Lacey Carla Guest Star Lisa Grady Janet Guest Star Ross Mackenzie Joe Harriman Guest Star Mandy McMillian Rita Guest Star Kiernan Shipka Sally Draper Guest Star Maura Soden Nurse Wilson Guest Star Jonathan Spencer Victor Manny Guest Star Marten Holden Weiner Glen Bishop Guest Star Richard Willgrubs Lynn Taylor Guest Star Matthew Weiner Writer, Director Robin Veith Writer