When director Baz Luhrmann took on the artistic challenge of modernizing Shakespeare's 16th-century play "Romeo and Juliet" for the grunge-listening youth of the '90s, he understood the importance of selecting the ideal actors for the leading roles. Hot off his Oscar nomination for "What's Eating Gilbert Grape," the young and charming Leonardo DiCaprio was an obvious choice for the love-struck Romeo. His Juliet, on the other hand, was a more difficult find. Although we now know the role eventually went to "My So-Called Life" star Claire Danes, she wasn't the first or even second choice.

Originally, Luhrmann had cast then-14-year-old Natalie Portman. The age was fitting for the original character, but when a 21-year-old DiCaprio came into the picture, the problematic age gap quickly became apparent. "[20th Century] Fox said it looked like Leonardo DiCaprio was molesting me when we kissed," Portman told The New York Times in 1996. Luhrmann agreed, saying in a 2022 interview with The New York Times, "She was 14. And when you see Leo in the flesh, he's a tall, young man and you just realized, she was too young. Natalie was amazing in the footage, but it was too much of a burden for her at that age." Luhrmann went through several more months of auditions before finding Danes. Although DiCaprio still had some years on the 17-year-old actress, DiCaprio spoke glowingly of his "Romeo + Juliet" co-star, saying, "She was the only girl that looked me in the eye in auditions" (via the New Yorker). It was a match made in Verona.