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 Steve Bannos Brentwood Doctor Mike Ostroski The Writer Christopher Kriesa Joe E. Brown Eric Matheny Joseph Cotten Scott Hislop Diamonds Dancer Dieterich Gray Photographer's Assistant Patrick Brennan Joe Chris Moss Diamonds Dancer Ryan Vincent Uncle Clive Michael Drayer Deputy Will Bonnie Mary-Pat Green Tracey Ron West Dr. Spindel 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 Garret Dillahunt Producer (uncredited) 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 Steve Bannos Brentwood Doctor Mike Ostroski The Writer Christopher Kriesa Joe E. Brown Eric Matheny Joseph Cotten Scott Hislop Diamonds Dancer Dieterich Gray Photographer's Assistant Patrick Brennan Joe Chris Moss Diamonds Dancer Ryan Vincent Uncle Clive Michael Drayer Deputy Will Bonnie Mary-Pat Green Tracey Ron West Dr. Spindel 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 Garret Dillahunt Producer (uncredited) 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 Steve Bannos Brentwood Doctor Mike Ostroski The Writer Christopher Kriesa Joe E. Brown Eric Matheny Joseph Cotten Scott Hislop Diamonds Dancer Dieterich Gray Photographer's Assistant Patrick Brennan Joe Chris Moss Diamonds Dancer Ryan Vincent Uncle Clive Michael Drayer Deputy Will Bonnie Mary-Pat Green Tracey Ron West Dr. Spindel 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 Garret Dillahunt Producer (uncredited) 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 Steve Bannos Brentwood Doctor Mike Ostroski The Writer Christopher Kriesa Joe E. Brown Eric Matheny Joseph Cotten Scott Hislop Diamonds Dancer Dieterich Gray Photographer's Assistant Patrick Brennan Joe Chris Moss Diamonds Dancer Ryan Vincent Uncle Clive Michael Drayer Deputy Will Bonnie Mary-Pat Green Tracey Ron West Dr. Spindel 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 Garret Dillahunt Producer (uncredited)