Suggestions by @paulcoolman2

Martin Scorsese

as Producer in A Million-Dollar Wound For Heller

Score: +2

James Mangold

as Director in A Million-Dollar Wound For Heller

Score: +3

Jonah Hill

as Willie Bioff in A Million-Dollar Wound For Heller

Score: +2

Stephen Graham

as Edward J. O'Hare in A Million-Dollar Wound For Heller

Score: +3

Vincent Kartheiser

as Westbrook Pegler in A Million-Dollar Wound For Heller

Score: +3

Harris Dickinson

as Robert Montgomery in A Million-Dollar Wound For Heller

Score: +3

Samantha Robinson

as Estelle Carey in A Million-Dollar Wound For Heller

Score: +3

Margot Robbie

as Sally Rand in A Million-Dollar Wound For Heller

Score: +3

David Dastmalchian

as Frank Nitti in A Million-Dollar Wound For Heller

Score: +3

Josh O'Connor

as Barney Ross in A Million-Dollar Wound For Heller

Score: +3

David Corenswet

as Nathan Heller, P.I. in A Million-Dollar Wound For Heller

Score: +2

Jessica Chastain

as Julie Nichols in Tootsie (2012)

Score: +1

Alice Pagani

as Isabella Torrisi in Mafia: The Old Country (2025)

Score: +3

Timothy Dalton

as Napoleon Solo in The Man from U.N.C.L.E. (1975)

Score: +3

Matt Damon

as Officer Jack Traven in Speed (2004)

Score: +1

Austin Butler

as Detective Lieutenant Edmund "Shotgun Ed" Exley in Denis Villeneuve's L.A. Confidential

Score: +3

Patricia Arquette

as Ma Barker in A True Crime For Heller

Score: +3

Austin Butler

as Ben in Anyone But You (Alternate Cast)

Score: +2

Marlon Brando

as Kasper Gutman in The Maltese Falcon (1981)

Score: +2

Harrison Ford

as Sam Spade in The Maltese Falcon (1981)

Score: +2