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 Alison Brie Trudy Campbell Guest Star Julia Ormond Marie Calvet Guest Star Bruce Greenwood Richard Burghoff Guest Star Caity Lotz Stephanie Guest Star Christine Estabrook Gail Holloway Guest Star Amy Ferguson Maureen Guest Star Fiona Gubelmann Eve Guest Star Spencer Treat Clark Kelly Guest Star Anna Osceola Clementine Guest Star Brett Gelman Daniel Guest Star Jeffrey Vincent Parise Vince Guest Star Helen Slater Sheila Guest Star Evan Arnold Leonard Guest Star Beth Hall Caroline Guest Star Evan Londo Gene Draper Guest Star Ryder Londo Gene Draper Guest Star Stephanie Drake Meredith Guest Star Caiden Milick Kevin Guest Star Aria Lyric Leabu Tammy Campbell Guest Star Brian F. Durkin Pilot Guest Star Ryan Ahern Brian Guest Star Francesca Ferrara Lorraine Guest Star Joey Honsa Angie Guest Star Matthew Weiner Executive Producer, Writer, Director Scott Hornbacher Executive Producer