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