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 John Cullum Lee Garner, Sr. Guest Star Talia Balsam Mona Sterling Guest Star Anne Dudek Francine Hanson Guest Star Rebecca Creskoff Barbara Katz Guest Star Aaron Hill Carl Winter Guest Star Adam Kaufman Bob Shaw Guest Star Joel Murray Fred Rumsen Guest Star Jay Paulson Adam Whitman Guest Star Andy Umberger Dr. Arnold Wayne Guest Star Aaron Hart Robert Draper Guest Star Julie McNiven Hildy Guest Star Brian Norris Mailroom Boy Guest Star Mario Piccirillo Waiter Guest Star Bess Rous Marjorie Guest Star Kiernan Shipka Sally Draper Guest Star Dominic Testa Vincent Guest Star Tim Hunter Director Tom Palmer Writer