Guest Stars Allison Tolman as Winzola "Winnie" McLendon Hamish Linklater as Jeb Magruder Chris Bauer as James McCord J.C. MacKenzie as Howard Hunt Martha Kelly as Rose Mary Woods Anne Dudek as Diana Oweiss Nat Faxon as Bob Haldeman Chris Messina as Agent Angelo Lano John Carroll Lynch as Acting Director L. Patrick Gray Carlos Valdés as Agent Paul Magallanes Patton Oswalt as Chuck Colson Kat Foster as Barbara Walters John Ventimiglia as Judge John Sirica Chris Conner as John Ehrlichman Nelson Franklin as Dick Moore Adam Ray as Ron Ziegler Vincent Di Paolo as Vito Reed Diamond as Mark Felt Johnny Berchtold as Jay Jennings Virginia Gardner as Sharon Ahna O'Reilly as Gail Magruder Beth Hall as Helen Thomas Beth Malone as Maria Co Starring Scott Michael Morgan as Bernard Barker Jordi Caballero as Eugenio Martinez Don DiPetta as Frank Sturgis Oscar Torre as Virgilio Gonzalez Forte Rodriguez as Marshall Edmund Korbin Marum as Raymond Liddy Angela Sprinkle as Tour Guide Aaron Goddard as Tom Snyder River Drosche as James Liddy Amelia Gray as Feminist #1 Benjamin Mackey as Tom Liddy Michael Paul King as Mike Douglas Aubree Bowen as Other Parent Christopher Mychael Watson as Chubby Checker Kenneth Hodges as Robert Jordan Hendricks as Young Republican Dominic Daniel as Bernard Shaw Alan Heitz as Crew Cut & Glasses Pat Asanti as Grumpy Gus Ericka Kreutz as Frances Liddy Lisa Carswell as Haldeman's Secretary Jay Jackson as Robert