Jon Hamm Don Draper Actor John Slattery Roger Sterling Actor Vincent Kartheiser Pete Campbell Actor January Jones Betty Draper Actor Christina Hendricks Joan Holloway Actor Elisabeth Moss Peggy Olson Actor Robert Morse Bertram Cooper Actor Rich Sommer Harry Crane Actor Aaron Staton Ken Cosgrove Actor Kiernan Shipka Sally Draper Actor Christopher Stanley Henry Francis Actor Jessica Paré Megan Draper Actor Jay R. Ferguson Stan Rizzo Actor Ben Feldman Michael Ginsberg Actor Kevin Rahm Ted Chaough Guest Star Mason Vale Cotton Bobby Draper Guest Star Alison Brie Trudy Campbell Guest Star Linda Cardellini Sylvia Rosen Guest Star Teyonah Parris Dawn Chambers Guest Star Charlie Hofheimer Abe Drexler Guest Star Brian Markinson Dr. Arnold Rosen Guest Star Yaani King Mondschein Phyllis Guest Star Stephen Mendel Morris Ginsberg Guest Star Harry Hamlin Jim Cutler Guest Star Lennon Parham Ginny Hunt Guest Star Nicole Hayden Beverly Farber Guest Star William Mapother Randall Walsh Guest Star Ross Marquand Paul Newman Guest Star Timi Prulhiere Nan Chaough Guest Star Henry LeBlanc Emcee Guest Star Rodney J. Hobbs Usher Guest Star Matthew Weiner Executive Producer, Writer Scott Hornbacher Executive Producer Tom Smuts Writer Chris Manley Director