Guest Stars Kiernan Shipka as Sally Draper Jared Harris as Lane Pryce Talia Balsam as Mona Sterling Elizabeth Rice as Margaret Sterling Embeth Davidtz as Rebecca Pryce Abigail Spencer as Miss Farrell Ryan Cutrona as Gene Hofstadt Eric Ladin as William Hofstadt Megan Henning as Judy Hofstadt James Immekus as Charlie Kevin Cooney as Edgar Raffit Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Derek Ray as Brooks Hargrove Mark Brandon as Man #1 Jeremy Scott Johnson as Ralph Buckland Austin Trace as Scott Brian Carpenter as Arnold Merriman Billy Finnigan as College Boy