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 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 Ashley LeConte Campbell as Nicky Firestone Bernard Bell as Dance Partner Leslie Kritzer as Martha Graham Joe Chrest as Dr. Pursch Hannah Aslesen as Reporter 2 (LB Naval Hospital) John Newberg as Dr. Cruse Mark Zeisler as Leonard Firestone Caitlin O'Connell as Meri Bell Emily Paige Hogan as Reporter 1 (LB Naval Hospital) Dennis Friebe as Reporter 3 (LB Naval Hospital) Maurice P. Kerry as Cassius Abby Glover as Cindy Boudreux A'Zaria Carter as Edgy Female Student Summer Menkee as Adult Cindy Boudreux John Schmedes as George H.W. Bush Logan Siu as Curious Male Student Holly Morris as Mrs. Audrey Boudreux Kaysi Bradley as Zoe Adama Elder as Adama Tom Clark as Architect Nicole Lamb as Excited Female Student Maddie Cravens as Starstruck Girl Tomecia Bradley as Zoe's Mother Bobbie Elzey as Barbara Bush Anya Koné as Younger Woman 1 Mary Meyer as Joan Karen Ragan-George as Leonore Annenberg Layla Walker as Lexi Byron Baudo as Walter Annenberg Kai Turé as Angelina Natasha Liu as Younger Woman 2 Sicily Ranieri as Resident Advisor Melissa Oulton Haas as Assistant Architect Fran Tabor as Diane