Director Michael Mann and Leonardo DiCaprio came very close to working together on "The Aviator" in the aughts, only for Mann to hand the project over to Leo's pal Martin Scorsese instead. But as it happens, Mann and DiCaprio had a previous close call in the 1990s, back when the latter was still just a whipper-snapper coming into his own after early career roles on the sitcoms "Parenthood" and "Growing Pains."

For as much as Mann is known for directing movies about careerists fueled by their obsessions (be they the type who makes an honest living or, as is more often the case, not), he also has a soft spot for biographical films that attempt to paint a complicated portrait of their subjects. At times he gets to combine these interests with projects like "Public Enemies" or "The Insider," both of which are as much character studies as they are dramatic thrillers based on real-world events.

It was seemingly his interest in films about real-life people's struggles with their personal demons that pushed Mann to attach himself to a James Dean biopic in 1993. DiCaprio, who was only 19 at that time, would make waves that same year by starring in the drama "What's Eating Gilbert Grape?" (the movie that earned him his first Oscar nod). And while Mann would test other actors to play the tragically short-lived star of "Rebel Without a Cause" and "East of Eden," it didn't taken long for him to settle on DiCaprio as his top pick for the role.

There was just one problem: Mann felt DiCaprio looked a little too kid-like to play the grown-up Dean.

You're Tearing Me Apart, Leo!

Leonardo DiCaprio is old enough now that it's easy to forget there was a time when he was commonly criticized for being too youthful-looking for many of the films he made as a young adult. To quote /Film's Josh Spiegel, "DiCaprio had been both blessed and cursed with the kind of cherubic face that turned him into a teenage heartthrob."

In an interview with Deadline, Michael Mann similarly cited DiCaprio's young appearance as the factor that "respectfully undid" his James Dean biopic:

"That was so weird about James Dean. It was a brilliant screenplay. And then it's 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. I think he must've been 19 at the time. And 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, and then he'd turn his face another direction and it's no, that's a young kid. I found the absolutely perfect act of the play, in about three years from that."

Not wanting to wait around for DiCaprio to "age" into the role, Mann wound up leaving the film. The Dean biopic would eventually come to fruition as the made-for-TV movie "James Dean" in 2001, with James Franco starring. It received polite if restrained applause from critics, with The Washington Post writing it re-creates Dean's life "with what might be called stunning adequacy."

Would Mann's "James Dean" have been better? Very possibly, but given what the director went and made in its place (a little film called "Heat"), perhaps it all worked out for the best.

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The post Michael Mann Almost Made a James Dean Biopic with a Young Leonardo DiCaprio appeared first on /Film.