Guest Stars Kiernan Shipka as Sally Draper Jared Harris as Lane Pryce Alison Brie as Trudy Campbell Christopher Stanley as Henry Francis Mark Moses as Herman "Duck" Phillips Peyton List as Jane Siegel Talia Balsam as Mona Sterling Elizabeth Rice as Margaret Sterling Laura Regan as Jennifer Crane Judy Kain as Olive Healy Carla Gallo as Karen Ericson Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Deborah Lacey as Carla Julie McNiven as Hildy Edin Gali as Kurt Derek Ray as Brooks Hargrove Anthony Burch as Marty Faraday Patrick John Hurley as Bruce Pike Jennifer Dawson as Ethel Shannon Welles as Nellie Veronica Taylor as Eleanor Francis Sewell Whitney as Bandleader
