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 Harry Hamlin Jim Cutler Guest Star Talia Balsam Mona Sterling Guest Star Teyonah Parris Dawn Chambers Guest Star Allan Havey Lou Avery Guest Star Trevor Einhorn John Mathis Guest Star H. Richard Greene Jim Hobart Guest Star Derek Ray Brooks Hargrove Guest Star Josh McDermitt George Payton Guest Star Kellie Martin Carolyn Glaspie Guest Star Elijah Nelson Neil Glaspie Guest Star Beth Hall Caroline Guest Star Evan Londo Gene Draper Guest Star Ryder Londo Gene Draper Guest Star Stephanie Drake Meredith Guest Star Jordan Fiderio Ellery Hargrove Guest Star Sammy Fiderio Ellery Hargrove Guest Star Jacob Guenther Julio Guest Star Michael Patrick McGill Dean Evans Guest Star Scott Allen Rinker Edwin Reed Guest Star Charlie DePew Sean Glaspie Guest Star Barry W. Levy Richard Glaspie Guest Star Joe Pistone Nick Guest Star Timothy Douglas Todd Guest Star Matthew Weiner Executive Producer, Writer, Director Scott Hornbacher Executive Producer Carly Wray Writer