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 Maggie Siff Rachel Menken Guest Star Elizabeth Reaser Diana Baur Guest Star Trevor Einhorn John Mathis Guest Star Rebecca Creskoff Barbara Katz Guest Star Sola Bamis Shirley Guest Star Ray Wise Ed Baxter Guest Star Jon Manfrelotti Art Garten Guest Star Jay Seals Marvin Woodman Guest Star Larisa Oleynik Cynthia Cosgrove Guest Star Greg Cromer Dennis Ford Guest Star Joshua LeBar Will Scully Guest Star Paul Johansson Ferg Donnelly Guest Star Devon Gummersall Stevie Wollcott Guest Star Nick Toren Tilden Katz Guest Star Stephanie Drake Meredith Guest Star Kirstin Ford Tricia Guest Star Rainey Qualley Cindy Guest Star Maliabeth Johnson Audrey Guest Star Carmela Corbett Charlotte Guest Star Stevie Nelson Lori Guest Star Dale Waddington Lillian Baxter Guest Star Alison Martin Viola Guest Star Sam Buchanan Libby Guest Star Matthew Weiner Executive Producer, Writer Scott Hornbacher Executive Producer, Director