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 Tommy 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 (Flight Attendant) Dan Butler I.E. Shinn Tygh Runyan Norma Jeane's 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 Ravil Isyanov Billy Wilder Tim Ransom Rudy Rob Brownstein Acting Coach Rob Nagle Radio Announcer Ethan Cohn Assistant to the Director Mike Ostroski The Writer Christopher Kriesa Joe E. Brown Eric Matheny Joseph Cotten Kiva Jump Ward Nurse at Norwalk Patrick Brennan Joe (Photo Shoot Photographer) Ryan Vincent Uncle Clive Vanessa Lemonides Marilyn Singing Voice (voice) Michael Drayer Deputy Will Bonnie Mary-Pat Green Tracey Ron West Dr. Spindel (Abortion Doctor) Scott Wilder Chloroform Man #1 Sal Landi Chloroform Man #2 Seth Meriwether 5th Helena Messenger Julián Rebolledo Trailer Announcer / Newsreel Announcer Allan Havey Dr. Greenson Tereza Rizzardi Ex-Athlete's Momma Mia McGovern Zaini Young Norma Jeane (voice) (uncredited) Garret Dillahunt Producer (uncredited) Judy Kain Severe Woman (uncredited)