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 Kate Norby Carol McCardy Guest Star Shayna Rose Rosemary Guest Star Teddy Sears Kicks Matherton Guest Star Darby Stanchfield Helen Bishop Guest Star Andy Umberger Dr. Arnold Wayne Guest Star Gary Ballard Waiter Guest Star Alison Brie Trudy Campbell Guest Voice La Monde Byrd Hollis Guest Star Allison Fleming Round Mom Guest Star Susan Grace Delia Guest Star Doug Hale Charlie Guest Star Maxwell Huckabee Robert Draper Guest Star Julie McNiven Hildy Guest Star Flora Plumb Gaudy Hat Guest Star Kiernan Shipka Sally Draper Guest Star Bridget Bedard Writer Tim Hunter Director