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 Linda Cardellini Sylvia Rosen Guest Star James Wolk Bob Benson Guest Star Teyonah Parris Dawn Chambers Guest Star Beth Hall Caroline Guest Star Charlie Hofheimer Abe Drexler Guest Star Michael Gaston Burt Peterson Guest Star Tyler Francavilla Lawrence Guest Star Pamela Dunlap Pauline Francis Guest Star Trevor Einhorn John Mathis Guest Star Brian Markinson Dr. Arnold Rosen Guest Star Ray Abruzzo Jonesy Guest Star David Starzyk Bob Grange Guest Star Kalani Queypo Master of Ceremonies Guest Star Loanne Bishop Barb Guest Star Patrick Mapel PFC Dinkins Guest Star Rob Brownstein Dr. Levy Guest Star Pat Skipper Tom Pruitt Guest Star Michael Bunin Photographer Guest Star Kerris Dorsey Sandy Guest Star Matthew Weiner Executive Producer, Writer Scott Hornbacher Executive Producer, Director