Guest Stars Clea DuVall as Malvina "Tommy" Thompson Ellen Burstyn as Sara Delano Roosevelt Cailee Spaeny as Anna Eleanor Roosevelt Kristine Frøseth as Young Betty 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 Michael Aronov as Rahm Emanuel Co Starring Evan Parke as Secret Service Agent Allen Taylor Donna Lynne Champlin as Mel Winter Cayden Boyd as Michael Ford Kelvin John Davis as Wilson Roosevelt Jerman Marc Hills as Jack Ford Eryn Rea as Gayle Ford Ben Cook as Steven Ford Judy Gold as Elizabeth Read Bernadette Quigley as Esther Lape John Connor as Radio Operator Aya Cash as Shirley Liebowitz Paprika Steen as Hortense Bloomer James J. Fuertes as Earl Miller Roslyn Ruff as Marian Anderson Tywayne Wheatt as Nathaniel Pendleton Sr. Jennifer Schottstaedt as Reporter Erik Bello as Secret Service Agent Ronnie Robert Bryan Davis as Sol Hurok Hope Brown as Walter Francis White Robert Frederick as Stump Speaker Anthony M. Bertram as Mr. Ferrar Tom Key as Funeral Guest Peyton Jackson as Nathaniel Pendleton Jr. Travon McEntyre as Alfred Anderson Andrew Fincham as Tuskegee Reporter 1 Ahmad Ghafouri as Tuskegee Reporter 2 Luke Sanderford as White House Tour Guide LeeAnn Ross as Hadiya Pendleton Jacob Dickey as Tony Orlando Charlotte Townsend as Malia's Science Teacher Rosemarie Lateefah Holder as Cleopatra Pendleton Jay DeVon Johnson as Philip Randolph