Madonna’s Best Films

By Rick Gonzales | Published

Madonna’s Best Films

As the world awaits the status of Madonna’s recovery from a near-fatal bacterial infection, they also are awaiting word on her upcoming Celebration tour, which was to kick off on July 15, 2023. With all of this waiting going on (and we do wish Madonna a speedy recovery to full health), we thought we’d take a look at her career as a movie star.

Madonna actually has some acting chops, and she has shown over her career that she knows how to use them. Perhaps her movie choices could have been better, but she did find the occasional decent film. Here are seven of her best films.

The Next Best Thing

The Next Best Thing is a 2000 dramedy starring Madonna as Abbie Reynolds, a heterosexual yoga instructor who decides to have a child with her gay best friend, Robert (Rupert Everett). They decide to raise the baby together and for five years all is fine. Then Abbie finds herself falling in love with a heterosexual man and wants to move away with him and take her son with them. Let the nasty court fight begin.

Shanghai Surprise

You might be able to call this Madonna movie a cult classic. It at least has a cult following. The Material Girl stars in this adventure-comedy alongside Sean Penn in Shanghai Surprise, a film set in 1930s China.

Penn plays Glendon Wasey, a con man who is finding times tough. Madonna is Gloria Tatlock, a missionary nurse who is looking to score a supply of opium to ease the pain and suffering of her patients.

Glendon decides to help her and together they meet up with a large amount of stolen opium. Unfortunately, they aren’t the only ones who want the drug.

Swept Away

Swept Away is a rom-com fish-out-of-water story directed by Guy Ritchie, who was married to Madonna at the time. Madonna plays Amber Leighton, the snooty, spoiled wife of a millionaire. The couple are on a private cruise from Italy to Greece and it doesn’t take long for Amber to reveal her claws.

She constantly berates deckhand, Giuseppe, even though she wants him to take her out on the ocean on the dinghy. He finally does, but a storm forces them to a deserted island. Roles reverse as Giuseppe’s survival skills take charge.

Truth or Dare

While not a feature film, Truth or Dare is a documentary that shows the life of Madonna while out on her 1990 Blonde Ambition World Tour. The documentary was a Madonna brainstorm and she tapped on director Alek Keshishian’s shoulder to make it happen.

The film follows Madonna through all the ups and downs of touring, but also gives an intimate and controversial look behind the scenes at Madonna and the entourage she travels with.

Dick Tracy

Of course, Madonna was going to play the bad girl in this comic book adaptation of Dick Tracy. Warren Beatty stars as the title character, a police detective whose sole purpose is to do away with organized crime. Madonna is Breathless Mahoney, a singer at Club Ritz who has her eyes on Dick and wants to steal him from his girlfriend, Tess Trueheart (Glenne Headly).

A League of Their Own

Although Madonna is just a part of an amazing ensemble cast in A League of Their Own, she makes the most out of it when she is on the screen. She plays “All the Way” Mae Moradabito, the centerfielder for the Rockford Peaches and the queen of troublemaking.

The movie is set during World War II and tells the story of the all-women’s baseball league. Madonna shines in her comedic performance which is highlighted by a raucous dance bar dance scene where she jumps, jives, and wails with two men.


Not going to lie here, we all knew that Madonna was talented, but her portrayal of Eva Perón in Evita was simply amazing. The musical biopic saw Madonna play Perón to such a perfect pitch that the material Girl earned serious critical acclaim and a feather in her cap – the Golden Globe award for Best Actress in a Musical or Comedy.