Jon Hamm Don Draper Actor, Director John Slattery Roger Sterling Actor, Director 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 Linda Cardellini Sylvia Rosen Guest Star James Wolk Bob Benson Guest Star Teyonah Parris Dawn Chambers Guest Star Harry Hamlin Jim Cutler Guest Star Matthew Weiner Executive Producer, Writer, Director Scott Hornbacher Executive Producer, Director Semi Chellas Writer Erin Levy Writer Jason Grote Writer Jonathan Igla Writer Andre Jacquemetton Writer Tom Smuts Writer Carly Wray Writer Janet Leahy Writer Jennifer Getzinger Director Michael Uppendahl Director Maria Jacquemetton Writer Phil Abraham Director Chris Manley Director