Guest Stars Clea DuVall as Malvina "Tommy" Thompson Jayme Lawson as Young Michelle Cailee Spaeny as Anna Eleanor Roosevelt Kristine Frøseth as Young Betty Saniyya Sidney as Sasha Obama Lexi Underwood as Malia Obama Robert Sean Leonard as Harry S. Truman Co Starring Evan Parke as Secret Service Agent Allen Taylor Ben Cook as Steven Ford Eryn Rea as Gayle Ford Marc Hills as Jack Ford Kelvin John Davis as Wilson Roosevelt Jerman Cayden Boyd as Michael Ford Elizabeth Cappuccino as Meg Maria Dizzia as Lucy Mercer Tory Trowbridge as Trudie Leslie Kritzer as Martha Graham Joe Chrest as Dr. Pursch Ashley LeConte Campbell as Nicky Firestone Hannah Aslesen as Reporter 2 (LB Naval Hospital) Bernard Bell as Dance Partner Maurice P. Kerry as Cassius Emily Paige Hogan as Reporter 1 (LB Naval Hospital) Mark Zeisler as Leonard Firestone Caitlin O'Connell as Meri Bell John Newberg as Dr. Cruse Dennis Friebe as Reporter 3 (LB Naval Hospital) Abby Glover as Cindy Boudreux A'Zaria Carter as Edgy Female Student John Schmedes as George H.W. Bush Fran Tabor as Diane Logan Siu as Curious Male Student Kai Turé as Angelina Melissa Oulton Haas as Assistant Architect Summer Menkee as Adult Cindy Boudreux Layla Walker as Lexi Karen Ragan-George as Leonore Annenberg Mary Meyer as Joan Anya Koné as Younger Woman 1 Bobbie Elzey as Barbara Bush Maddie Cravens as Starstruck Girl Tomecia Bradley as Zoe's Mother Adama Elder as Adama Nicole Lamb as Excited Female Student Tom Clark as Architect Holly Morris as Mrs. Audrey Boudreux Kaysi Bradley as Zoe Byron Baudo as Walter Annenberg Sicily Ranieri as Resident Advisor Natasha Liu as Younger Woman 2