Guest Stars Kiernan Shipka as Sally Draper Jared Harris as Lane Pryce Alison Brie as Trudy Campbell Christopher Stanley as Henry Francis Patrick Cavanaugh as Smitty Chelcie Ross as Connie Charles Shaughnessy as Saint John Powell Ryan Cartwright as John Hooker Joseph Culp as Archie Whitman J. Patrick McCormack as Kenneth Dillon Co Starring Jared S. Gilmore as Bobby Draper Alexa Alemanni as Allison Deborah Lacey as Carla Edin Gali as Kurt Brynn Horrocks as Abigail Whitman Brandon Killham as Dick Leonard Kelly-Young as Cooperative Head Bobby Hall as Farmer 1 Kevin Scott Allen as Farmer 2