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