From ‘Swept Away’ to ‘Desperately Seeking Susan,’ see where your favorites rank!
Left: ‘Dick Tracy’ (1990); Right: ‘Desperately Seeking Susan’ (1985)Sunset Boulevard/Corbis via Getty (2)
Madonna has been many things in her 40-year reign as a pop culture icon. More than just a pop star, she’s long been known as a fashion plate, a boundary pusher and a constantly evolving force of feminine strength. She’s also been known as an actress, though to put it mildly, she hasn’t always been called a very good one.
While we’ll definitely admit that not every Madonna movie has been a masterpiece, there’s no denying that the diva’s film career has been a major part of her ever-changing image. From classic documentaries to musicals to comic book adaptations to rom-coms, here’s our ranked list of Madonna movies from worst to best.
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11. Swept Away (2002): Worst Madonna movies
Madonna in Swept Away (2002)Sony Pictures Releasing/MovieStillsDB
On paper, a remake of a provocacative ’70s art film from a trailblazing woman director would seem to be a natural fit, but Swept Away, adapted from Lina Wertmüller‘s 1974 film of the same name, ended up being one of the biggest flops of Madonna’s career.
Directed by Madonna’s then-husband, Guy Ritchie, and starring her as a wealthy woman who ends up stranded on an island with a handsome Italian man, Swept Away generated much tabloid buzz thanks to Madonna’s high-profile marriage, but made back just a fraction of its budget and was met with universally negative reviews.
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10. Shanghai Surprise (1986)
Madonna in Shanghai Surprise (1986)Dave Hogan/Getty
When it came to being in her husbands’ movies, Madonna never had the best luck. She starred in Shanghai Surprise opposite her first husband, Sean Penn, playing a ’30s-era missionary nurse who gets caught up in a sticky situation involving stolen opium.
Like Swept Away, Shanghai Surprise, which was produced by none other George Harrison, received a lot of attention in the media but didn’t do well at the box office and was panned by critics.
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9. The Next Best Thing (2000)
Madonna and Rupert Everett in The Next Best Thing (2000)Paramount Pictures/MovieStillsDB
Madonna played a woman who decides to have a 𝚋𝚊𝚋𝚢 with her gay best friend in this rather far-fetched comedy. Inevitably, the situation becomes even more complicated when she later falls for a hetero𝓈ℯ𝓍ual man, leading to a custody battle.
While The Next Best Thing was poorly reviewed, the cover of “American Pie” Madonna recorded for the movie became a hit.
8. Body of Evidence (1993)
Madonna in Body of Evidence (1993)Murray Close/Sygma/Sygma via Getty
Following the blockbuster success of Basic Instinct in 1992, erotic thrillers were all the rage and Madonna starred in one of her own, the widely derided Body of Evidence.
Madonna played a devious femme fatale who lives on a houseboat and manipulates everyone in her orbit, and while the film was poorly reviewed and dismissed as a vanity project (complete with plenty of nudity), it has its so-bad-it’s-good moments, thanks to Madonna’s glamorous posturing and the ridiculous plot twists.
7. Dangerous Game (1993)
Madonna in Dangerous Game (1993)MGM/MovieStillsDB
Released not long after Body of Evidence, Dangerous Game is a gritty drama that stars Madonna as an actress appearing in a film-within-the-film. Soon enough, things start to break down, making this one of the darker movies in Madonna’s filmography.
Reviews were mixed, and Madonna herself trash talked the film, but it makes for somewhat intriguing viewing since it goes against her typically glamorous image.
6. Who’s That Girl (1987): Comedy Madonna movies
Madonna in Who’s That Girl (1987)Oscar Abolafia/TPLP/Getty
In this comedy, Madonna played a woman who gets framed for murder and convinces an unsuspecting man to help her track down the real 𝓀𝒾𝓁𝓁ers. Along the way, they pick up a cougar (just go with it) and fall in love.
Who’s That Girl, like many other Madonna movies, didn’t do particularly well, but its modern take on classic screwball humor combined with the star’s sassy style makes it better than some of her other films. The title sequence, featuring an adorable animated version of Madonna, is particularly memorable.
5. Dick Tracy (1990)
Madonna and Warren Beatty in Dick Tracy (1990)Sunset Boulevard/Corbis via Getty
Dick Tracy, directed by and starring Warren Beatty, Hollywood’s legendary ladies’ man and Madonna’s boyfriend at the time, was one of Madonna’s biggest films.
The adaptation of the classic ’30s comic stands out for its over-the-top style and eye-popping color palette. Madonna earned praise for her performance as a 𝓈ℯ𝓍y nightclub singer, and performed a number of memorable songs on the movie’s soundtrack. She won an Oscar for Best Original Song for her jazzy number “Sooner or Later,” and the movie still feels fresh today, thanks to its bold aesthetic and Madonna’s sizzling performance.
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4. Evita (1996): Musical Madonna movies
Madonna in Evita (1996)Buena Vista Pictures/MovieStillsDB
In this lavish historical musical, Madonna played Eva Perón, the First Lady of Argentina who lived a tumultuous life before she passed away at just 33 in 1952.
Madonna fought hard to get the role and gave it her all, showing a more serious side of herself as an actress and belting it out like never before on the soundtrack. Her vocal training for Broadway style singing paid off, as she won her second Best Original Song Oscar for her performance of “You Must Love Me.”
3. A League of Their Own (1992)
Madonna in A League of Their Own (1992)Columbia Pictures/MovieStillsDB
A League of Their Own boasts a star-studded cast, including Geena Davis, Tom Hanks and Rosie O’Donnell; a fascinating real-life story; a warm sense of humor and an inspiring message, making it one of the only Madonna movies that’s genuinely crowd-pleasing and fun for the whole family.
Based on the story of the All-American Girls Professional Baseball League, which formed during World War II to keep America’s Pastime going while men were fighting, the film was a hit, and Madonna was well-cast as a sassy and streetwise dancer who becomes the team’s center fielder.
2. Truth or Dare (1991)
Madonna with her dancers in Truth or Dare (1991)Michael Ochs Archives/Getty
For someone with such a larger than life presence, it makes sense that one of the best Madonna movies features her playing herself.
Truth or Dare, a documentary following Madonna on her Blond Ambition tour, captured the singer at the height of her powers. Shot in elegant black-and-white, the film shows Madonna to be alternately funny, glam, exasperating and maternal — sometimes all in one scene!
The film is eternally captivating, thanks in large part to Madonna’s rapport with her background dancers and the complex questions it raises about celebrity and the nature of performance. Is this the “real” Madonna? Who knows, but it’s fun to watch her no matter what.
1. Desperately Seeking Susan (1985): Best Madonna movies
Rosanna Arquette and Madonna in Desperately Seeking Susan (1985)Sunset Boulevard/Corbis via Getty
Desperately Seeking Susan is the ultimate Madonna movie. This comedy, which stars Rosanna Arquette as a bored New Jersey housewife who becomes obsessed with a cool, fashionable New York layabout (Madonna, obviously) is filled to the brim with fabulous ’80s style, and provides the ideal showcase for Madonna’s charisma.
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The movie gave Madonna her first starring role, and Like a Virgin, the album that shot her into the pop stratosphere, came out just before it was released, elevating her from a scrappy rising star to a worldwide phenomenon.
Written and directed by women, Desperately Seeking Susan perfectly mixes breezy humor and feminist empowerment, and nearly 40 years after it was first released the film, and Madonna’s performance, remain absolutely delightful.
