Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Chris Messina as Reese Lansing Marcia Gay Harden as Rebecca Halliday Grace Gummer as Hallie Shea Jane Fonda as Leona Lansing B.J. Novak as Lucas Pruit Jimmi Simpson as Jack Spaniel Brian Howe as Barry Lasenthal Derek Webster as Rodger Hutchinson Mary McCormack as Molly Levy Clea DuVall as Lilly Hart Keith Powell as Wyatt Geary Paul Lieberstein as Richard Westbrook A. Leslie Kies as Alex Thacker Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Thomas Matthews as Martin Stallworth Riley Voelkel as Jennifer "Jenna" Johnson Victoria Garcia-Kelleher as Millie John Hawkinson as Rudy Emily Wilson as Shannon Bryer Matthew Rocheleau as White House Staffer Amy Vorpahl as Gwen Michael Hyland as Bartender Patrick Birkett as Elderly Man Angela Fornero as White House Staffer Nick Marcucci as Eli Shapiro Jane Runnalls as FBI Tech