Check out the All-Star Cast for Romeo + Juliet Now and Then

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When Romeo + Juliet came out, DiCaprio admitted that he didn’t know how the concept—Elizabethan language in a hyper-modern setting—would be received, no matter how timeless the material.

But “I have to say,”He 1997 i-D interview? “the first time I knew it was working was the first day of work. It actually seemed more natural, more ‘meant to be’ than a traditional version.”

“Even though it’s a fantasy world,”He explained that “it has a lot of modern references in it, especially with the violence and gang warfare, so it made me feel a lot closer to home. I think Shakespeare probably would have wanted his work to live on through the years, become a timeless piece that could adapt to the future.”

And of playing Romeo, DiCaprio said, “It was interesting once I really started to research him, because you have this pre-planned idea of what Romeo’s supposed to be, just some fluffy romantic type of guy, but then you sort of realize that he was a hopeless romantic, and then he meets Juliet. Juliet responds, “Alright, look, if I’ve got any balls, you should marry me now, and risk everything.”

“So he risks everything—his whole life, his whole family, everything—and he marries this girl, which is such an honorable thing to do if you really believe in somebody, if you believe in love like that, especially at that age, especially to risk your life. It’s the ultimate tragedy and the ultimate love story.”