Jon Hamm Don Draper Actor, Director 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 James Wolk Bob Benson Guest Star Brian Markinson Dr. Arnold Rosen Guest Star Gary Basaraba Herb Rennet Guest Star Trevor Einhorn John Mathis Guest Star Yaani King Mondschein Phyllis Guest Star Morgan Rusler Mack Johnson Guest Star Julie Alexander Ernestine Guest Star Megan Ferguson Ms. Swenson Guest Star Kip Pardue Tim Jablonski Guest Star John Sloman Raymond Geiger Guest Star Collette Wolfe Brenda Guest Star Katie Walder Sherry Guest Star Oliver Muirhead John Echolls Guest Star Stephanie Drake Meredith Guest Star Kit Williamson Ed Guest Star Brandon Killham Young Dick Whitman Guest Star Brynn Horrocks Abigail Whitman Guest Star Keenan Henson Doug Guest Star Bryan Chesters Bill Guest Star Toni Torres Lucy Guest Star Peter Arpesella Waiter Guest Star Martin Dew Hugh Hibbert Guest Star Matthew Weiner Executive Producer, Writer Scott Hornbacher Executive Producer Jonathan Igla Writer