Leonardo DiCaprio has played several real-life figures throughout his remarkable career, including Jim Carroll in The Basketball Diaries, Frank Abagnale Jr in Catch Me If You Can, Howard Hughes in The Aviator and Jordan Belfort in The Wolf of Wall Street. Despite that success though, one project slipped through the net when DiCaprio once came close to portraying the legendary actor James Dean.

Dean remains a cultural touchstone of American teenage disillusionment following his excellent performances in Rebel Without a Cause, East of Eden, and Giant. However, at just the age of 24, Dean tragically died in a car crash.

DiCaprio, who at some point in his early life bore a striking physical resemblance to Dean, considered the legendary actor one of his heroes and very nearly portrayed him in a film set to be directed by Michael Mann in the 1990s.

James Dean biopic scrapped over Leonardo DiCaprio's age

“It was a brilliant screenplay,” Mann once told Deadline. “And then it’s [the question of] who the hell could play James Dean? And I found a chap who could play James Dean, but he was too young. It was Leo. We did a screen test that’s quite amazing.”

At the time, DiCaprio was just 19 years old, five years younger than Dean had been when he died in a fiery car crash. The problem for the young actor was that he just looked too young. There was indeed a resemblance with Dean, but his still-boyish looks meant he wasn’t quite right for the role.

“From one angle, he totally had it with him. I mean, it’s brilliance. He would turn his face in one direction, and we see a vision of James Dean,” Mann remembered of the screen test DiCaprio gave. “Then he’d turn his face another direction, and it’s no, that’s a young kid.”

Mann went on to admit that DiCaprio would have been perfect for the role around three years later. However, by that point, both the director and actor had moved on to different projects, and Mann couldn’t imagine bringing in a different actor. He noted, “He respectfully undid the James Dean bio for me.”

DiCaprio has proven that he’s capable of being an actor playing an actor, having given one of his best-ever performances as Rick Dalton in Quentin Tarantino’s Once Upon a Time in Hollywood. Cinema fans will never know whether he’d been able to quite stand up to Dean’s legacy, especially at such a young age, and the project has fallen into unknown annals of American film history.