The three roles Leonardo DiCaprio “didn’t feel ready” to play: “I took the meeting”

Leonardo DiCaprio has had an extraordinary career, the kind most aspiring actors hardly dare to dream of when they first feel the pull toward the profession. It already feels massive, powerful and almost too good to be true – yet somehow, it could have been even bigger.

The key thing to note about DiCaprio is that he has not only been successful but also remarkably careful in his choices. He’s a self-taught talent, and while that can allow for raw brilliance untouched by tradition or structure, it can just as easily result in poor decisions when people panic and start saying yes to everything. DiCaprio never did that.

Even his first projects feel considered as he showed his potential across the board from dramas to comedies to even a western. By the time he was cast to play Romeo, his leading man power was obvious and locked in, but even beyond that point, he’s very clearly only said yes to things he’s excited by, and the things he can do.

Maybe, to some degree, DiCaprio’s self-made lingering insecurity saves him. Especially in the earlier days, there was still some doubt in him as he didn’t want to take on a role and find himself drowning in the deep end, diving in somewhere that he actually couldn’t tread water to make it work. He seemed to have the foresight that getting into something too big too quick could be the death of him, leading him to turn down huge offers.

In particular, he turned down three major propositions, all in quick succession, and all at a very particular moment in his career. The first came in 1995, when the topic of his offer to play Robin in Batman Forever came up, about which he recalled to Shortlist, “I had a meeting with Joel Schumacher”, but he said no.

“I took the meeting, but didn’t want to play the role. Joel Schumacher is a very talented director, but I don’t think I was ready for anything like that,” he said, and that word ‘ready’ is the essential one. DiCaprio seemed to realise that a movie of that scale would be too much too soon. He didn’t want to dive into the mass world of comic book adaptations when he wasn’t even done establishing himself yet, or figuring himself out.

The other two rejections followed suit. “I did have a meeting with George Lucas about that,” he said, skirting around his other ‘no’, which was in response to the offer to play Anakin Skywalker in the Star Wars prequel movies, in the late 1990s and early 2000s. The reason was the same as he said he “just didn’t feel ready to take that dive. At that point”.

Finishing the hat-trick was Spider-Man. In the early 2000s, DiCaprio was called in for the role Tobey Maguire would become famous for, reiterating like a broken record, “That was another one of those situations, similar to Robin, where I didn’t feel ready to put on that suit yet”.

Maybe this is DiCaprio being shy and nervous to step into such lofty roles. However, it could also be the sly way he’s avoided falling into any kind of ‘cinematic universe’, rejecting superhero roles or big sci-fi productions to instead stick to the projects that he feels passionate about.

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