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Madonna rose to fame as a pop music superstar in the 1980s. In the 1990s, she was known around the world, but she sought to make an even bigger name for herself — not as a singer, but as an actor.

Madonna in 'Evita
Madonna in ‘Evita’ | Getty Images

Madonna acting in ‘Evita’ was her crossover from music to movies

Madonna had appeared in movies in the 1980s and ’90s including Shanghai Surprise and Dick Tracy. But when it was revealed that Andrew Lloyd Webber’s famed stage musical Evita was being made into a movie, Madonna felt called to the role.

Madge kept a diary of her experiences throughout the process of making the movie, which was published in Vanity Fair in November 1996, one month before the movie’s release. In it, she reflected on her journey from being cast to the movie hitting the theaters.

“I remember sitting down during Christmas of ’94 and writing an impassioned letter to the director, Alan Parker, listing the reasons why I was the only one who could portray her, explaining that only I could understand her passion and her pain,” Madonna wrote. “I can honestly say that I did not write this letter of my own free will. It was as if some other force drove my hand across the page.”

Evita was well-received, particularly with Madonna’s portrayal of former Argentinian First Lady Eva Perón. After attempting to break into the film industry for years, Madonna had made her mark.

Madonna singing and playing guitar
Madonna performs during her “Sticky and Sweet” world tour at Olympic Stadium on September 6, 2008 in Rome, Italy | Elisabetta Villa/Getty Images

Madonna felt ‘lonely and alienated’ while filming ‘Evita’

Even though Evita was a fulfilling experience for Madonna in the end, it was a long way to get there. While filming the movie in Argentina, she didn’t feel connected to the people and places around her at all.

“As I descend further into this labyrinth called moviemaking I am stunned by the number of possibilities for feeling lonely and alienated,” she wrote in her diary. “While I have become more and more accepted by the Argentinians, I feel increasingly cut off from the rest of the world. I rarely speak to my friends and when I do I find it impossible to share what I am experiencing.”

“In the beginning I received letters and care packages all the time. Now I come home and my fax machine is empty and there are no phone messages,” she continued. “My family and friends are the people in the movie. They have seen me bare my soul and yet they know nothing about me. There is a kind of shyness that occurs when someone is required to be extremely vulnerable in front of complete strangers.”

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Madonna was committed to portraying Eva Perón

Madonna immersed herself in Argentinian culture to prepare for the role. She took tango lessons and began working with a vocal coach to improve her singing since all of Evita‘s dialogue is sung.

Madonna even changed her appearance to look as much like Perón as possible. She wore brown contact lenses and had a bridge put on her teeth to hide her iconic tooth gap.

She was committed to the role, but that didn’t mean it was fun for her. “I’m still trying to get used to my brown contacts, which make me feel dizzy, nauseated, and permanently in the dark. Or maybe this is what happens when you stay in your hotel room all day,” she wrote. “I’ve got to get out more — I’m starting to talk to my dog too much.”