Ana de Armas Norma Jeane Adrien Brody The Playwright Bobby Cannavale The Ex-Athlete 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 Norma Jeane's Father David Warshofsky Mr. Z Michael Masini Tony Curtis Chris Lemmon Jack Lemmon Ned Bellamy Doc Fell Sonny Valicenti Casting Director Tatum Shank Dick Tracy Andrew Thacher Jiggs Ravil Isyanov Billy Wilder Tim Ransom Rudy Rob Brownstein The Acting Coach Rob Nagle Radio Announcer Jeremy Shouldis Tuxedo #2 Ethan Cohn Assistant to the Director Scott Hislop Diamonds Dancer Michael Drayer Deputy Will Bonnie Seth Meriwether 5th Helena Messenger