Ana de Armas Norma Jeane Adrien Brody The Playwright Bobby Cannavale The Ex-Athlete Garret Dillahunt Sara Paxton Miss Flynn Lucy DeVito Ex-Athlete's Niece Julianne Nicholson Gladys Scoot McNairy Tom Ewell / Richard Sherman Xavier Samuel Cass Chaplin Caspar Phillipson The President Evan Williams Eddy G. Robinson Jr. Rebecca Wisocky Yvet Toby Huss Whitey Catherine Dent Jean Haley Webb Brooke Dan Butler I.E. Shinn Tygh Runyan Father David Warshofsky Mr. Z Michael Masini Tony Curtis / Josephine Chris Lemmon Jack Lemmon / Daphne Ned Bellamy Doc Fell Sonny Valicenti Casting Director Tatum Shank Dick Tracy Andrew Thacher Jiggs Lidia Sabljic Sweet Sue Isabel Dresden Doc Fell's Nurse Ravil Isyanov Billy Wilder Tim Ransom Rudy Judy Kain Severe Woman Time Winters George Sanders Rob Brownstein The Acting Coach Emil Beheshti Brentwood Doctor