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 Mary McCormack as Molly Levy Derek Webster as Rodger Hutchinson Keith Powell as Wyatt Geary Clea DuVall as Lilly Hart 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 Patrick Birkett as Elderly Man Michael Hyland as Bartender Angela Fornero as White House Staffer Nick Marcucci as Eli Shapiro Jane Runnalls as FBI Tech