Special Guest Stars John Slattery as Roger Sterling Guest Stars Kiernan Shipka as Sally Draper Robert Morse as Bertram Cooper Anne Dudek as Francine Hanson Joel Murray as Fred Rumsen Julie McNiven as Hildy Talia Balsam as Mona Sterling Aaron Hart as Robert Draper Andy Umberger as Dr. Arnold Wayne Jay Paulson as Adam Whitman Rebecca Creskoff as Barbara Katz Adam Kaufman as Bob Shaw Bess Rous as Marjorie Aaron Hill as Carl Winter Brian Norris as Mailroom Boy Dominic Testa as Vincent Mario Piccirillo as Waiter