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Leonardo DiCaprio is an acclaimed, Oscar-winning actor who basically has his pick of roles. But early in his career, he had to fight for the parts that earned him his reputation as one of the most talented actors in Hollywood.
When director Baz Luhrmann was casting his modern Shakespearean drama, Romeo + Juliet, DiCaprio was already making a name for himself. He had already been nominated for an Oscar (in 1993 for What's Eating Gilbert Grape?) and was building an impressive post-Growing Pains resume. Even so, Luhrmann hadn't heard of the then up-and-coming actor, Vanity Fair (opens in new tab) reports.
"When I saw Leonardo I thought, God, that's how he should look. But can he act?" the director told iHeart Radio (opens in new tab). "Then I found out he was the pre-eminent young actor."
But it wasn't DiCaprio's reputation or resume that got him the coveted part of Romeo in Luhrmann's adaptation. It was his friends and knack for grand gestures.
DiCaprio enlisted several of his famous friends (who, at the time rather infamously included (opens in new tab) the likes of Tobey Maguire, Lukas Haas, and Kevin Connolly), and filmed a short version of the play. Oh, and as if that weren't enough, he flew to Luhrmann's home in Australia to personally deliver his very creative audition.
"He came down to Australia and he brought all these friends and we made a whole video of the show with other actors," Luhrmann said. "I won't say who, it will never be seen; I realized that I couldn't make it without him."
So basically, it was DiCaprio's triple threat combination of looks, talent, and good old fashioned gumption that landed him the iconic role—and we're glad it did. We couldn't imagine a more perfect '90s Romeo.

Kayleigh Roberts is a freelance writer and editor with more than 10 years of professional experience. Her byline has appeared in Marie Claire, Cosmopolitan, ELLE, Harper’s Bazaar, The Atlantic, Allure, Entertainment Weekly, MTV, Bustle, Refinery29, Girls’ Life Magazine, Just Jared, and Tiger Beat, among other publications. She's a graduate of the Medill School of Journalism at Northwestern University.
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