Guest Stars Clea DuVall as Malvina "Tommy" Thompson Cailee Spaeny as Anna Eleanor Roosevelt Ellen Burstyn as Sara Delano Roosevelt Jackie Earle Haley as Louis McHenry Howe Saniyya Sidney as Sasha Obama Lexi Underwood as Malia Obama Judy Greer as Nancy Howe Rhys Wakefield as Dick Cheney Derek Cecil as Donald Rumsfeld Rosalind Chao as Tina Tchen Co Starring Evan Parke as Secret Service Agent Allen Taylor Opal Alladin as Robin Roberts Jenna Kanell as Activist 1 Cory Scott Allen as Secret Service Agent Austin Bill Winkler as Secret Service Agent Alan Wells as J. Edgar Hoover Amber Erwin as Housekeeper Jia Patel as Malia's School Friend 6 Caitlyn Mclaughlin as Malia's School Friend 5 Madison Alsobrook as Malia's School Friend 1 Matthew Sean Blumm as Special Agent Richard Keiser Zoe Browning as Malia's School Friend 2 Solina Galo as Malia's School Friend 3 Mimi Kelley as Malia's School Friend 4 Kelley Pereira as ERA Telethon Caller 2 Morgan Petersen as First Lady's Executive Assistant Madison Hatfield as ERA Telethon Caller 3 Alexandria Benford as ERA Telethon Caller 1 Jill Ginsberg as Decorator Wes Jetton as Activist 3 Jana Allen as Missy LeHand Brenna Palughi as Jill Ruckelshaus Jason Jamal Ligon as Activist 2