Who’s That Girl?

Who’s That Girl is an American comedy movie released in 1987. The movie follows the story of a girl who’s falsely accused of murdering her boyfriend and is later on sent to jail.

Madonna had to convince Warner Bros and the producers of the movie that she’s ready for a project like that after her previous acting attempt failed.

Even though the movie itself wasn’t that big of a hit, its soundtrack went on to sell six million copies worldwide and it became a commercial success. Three of Madonna’s songs, Who’s That Girl, Love Commotion and The Look of Love took in popularity, with the movie soundtrack becoming her sixth number one single on the US Billboard Hot 100.

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Evita

Evita is a 1996 American musical drama movie that depicts the life of Eva Perón, showing her beginnings, rise to fame, her political career and death only at the mere age of 33. Madonna was playing Eva, the leading role in the movie, something she’d always wanted to do – in fact, she even wrote to the director herself, explaining why she’d be perfect for the role!

Madonna has released three singles from the Evita soundtrack album out of which two got widely popular: Don’t Cry for Me Argentina and You Must Love Me, a song that won an Academy Award for Best Original Song in 1997.

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Dick Tracy

Dick Tracy is an action comedy movie from 1990. The plot is about a detective’s love relationships as well as his conflicts and interactions with a big crime boss. Madonna starred in the role of Breathless Mahoney and to accompany her role in the movie, she released I’m Breathless, a soundtrack album inspired by the film setting.

Even though the movie got mixed reviews, it was a success both at the box office and at awards time. It got nominated for seven Academy Awards and won three: Best Original Song, Best Makeup and Best Art Direction.

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A League of Their Own

A League of Their Own is a sports comedy drama movie released in 1992. It tells a fictionalized side of the real-life All-American Girls Professional Baseball League: two sisters join it and struggle to help the league succeed.

In the movie, Madonna plays the part of Mae Mordabito, a baseball player on an all-women’s team alongside other big movie stars such as Geena Davis and Tom Hanks. Madonna recorded the theme song, This Used to Be My Playground that instantly became a Hot 100 number-one hit.

In 2012, A League of Their Own was selected for preservation in the United States National Film Registry due to its cultural and historical significance.

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Desperately Seeking Susan

Desperately Seeking Susan is a comedy-drama movie that was released in 1985. The story is about two women, who come of two very different backgrounds that somehow manage to connect with one another by their interaction in a personal newspaper column.

Madonna first recorded a song specifically meant for the movie – she titled it Desperately Seeking Susan though in the end, Into the Groove was used instead.

The movie was the first major screen role of Madonna and it was pretty well received among the critics. The New York Times named Desperately Seeking Susan as one of the 10 best movies of 1985.

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Swept Away

Swept Away is a romantic comedy movie that was written and directed with Madonna’s then-husband Guy Ritchie. The movie was released in 2002 and it was supposed to be a remake of a 1974 movie with the same name.

Madonna plays Amber Leighton, an arrogant 40 year-old that nothing makes happy – not even a vacation on a private cruise. However, once stuck on a deserted island with the ship’s first mate, things start to change for the two of them.

The movie received mostly negative reviews and it is considered to be a box office bomb.

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Shanghai Surprise

Shanghai Surprise is a 1986 British comedy movie directed by Jim Goddard in which Madonna starred alongside her then-husband Sean Penn.

The screenplay was adapted from Tony Kenrick’s 1978 novel Faraday’s Flowers. The story revolves around Glendon Wasey, a fortune hunter and Gloria Tatlock, a missionary nurse who’d like to try opium to ease the sufferings of her patients.

Shanghai Surprise didn’t go very well with the global audience nor with the critics, as it received mostly poor reviews.

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