Madonna’s 10 Best Movies, According To Rotten Tomatoes

Over the past four decades, no single pop star has reinvented themselves more often and effectively than Madonna. Since her eponymous debut album in 1983, Madonna has gone to make 14 albums and win seven Grammy Awards, becoming the wealthiest woman in the music business during that span.

In addition to her music career, Madonna has also starred in roughly 20 feature films to date. She’s worked with some of the finest film directors in her career, including Warren Beatty, Woody Allen, Penny Marshall, Abel Ferrera, and more. She’s even directed two features, Filth and Wisdom and W.E. For more, here are Madonna’s 10 Best Movies, according to Rotten Tomatoes.

10 Shadows And Fog (1992) 50%

Woody Allen’s black and white comedy Shadows and Fog concerns a murderous strangler on the loose in a small village. When accountant Kleinman (Allen) is rousted out of bed by an angry mob on the hunt for the killer, he gets swept up in terrifying murder mystery.

Madonna plays Marie in the film, a seductive artist prone to adulterous affairs. When clown-artist Paul (John Malkovich) has an affair with Marie, the act prompts his wife Irmy (Mia Farrow) to have sex with Student Jack (John Cusack) while the killer continues to lurk.

9 Vision Quest (1985) 57%

Although she’s credited as Singer at the Club, it doesn’t change the fact that Vision Quest marks the second feature film of Madonna’s movie career behind the 1979 title A Certain Sacrifice.

Directed by Harold Becker, Vision Quest is a coming-of-age sports drama in which a young student-athlete named Louden Swain (Matthew Modine) dedicates himself to becoming the greatest athlete he can be. To do so, Louden rids all distractions from his life to focus on athletic improvement. But when a drifter named Carla (Linda Fiorentino) rents a vacant room in his home, he falls head over heels in love with her.

8 Die Another Day (2002) 57%

Madonna not only sang the iconic theme song for the 007 film Die Another Day, but she also appeared in the film as the uncredited Verity. She earned a Golden Globe nomination for Best Original Song.

Starring Pierce Brosnan as James Bond and Halle Berry as his reluctant sidekick Jinx Johnson, the plot of the film revolves around a diamond magnate who may be involved with a North Korean terrorist out to create an intergalactic weapon. Madonna also made a four-minute music video for the title track Die Another Day.

7 Dick Tracy (1990) 62%

In Warren Beatty’s comic-book crime picture Dick Tracy, Madonna plays the role of Breathless Mahoney. Her character is not only the chief entertainer at Club Ritz, but she’s also the lone eyewitness to many of Caprice’s (Al Pacino) criminal endeavors.

For her singing performance in the film, Beatty hired acclaimed theatrical songwriter Stephen Sondheim to write five new songs that Madonna could deliver on stage. One of Sondheim’s songs, “Sooner or Later,” was nominated for an Academy Award.

6 Evita (1996) 63%

In Alan Parker’s musical biopic Evita, Madonna portrays the real-life figure Evita Duarte de Peron, an Argentian actress who rose to prominence upon marrying the nation’s President, Juan Peron (Jonathan Pryce).

The stage-to-screen adaptation of the hit Broadway musical won an Oscar Award for Andrew Lloyd Weber’s original song “You Must Love Me.” Plot-wise, Eva Peron endures a love-hate relationship from her fellow nationals as her husband’s political career becomes more and more complicated.

5 The Universe Of Keith Haring (2008) 68%

The life work of gay New York street artist Keith Haring is the celebrated subject of Christina Clausen’s 2008 documentary. Several fellow artists from New York and elsewhere pay tribute to the lasting legacy Haring left behind, whose life was cut short of AIDS-related complications in 1990. He was 31 years old.

In addition to Madonna appearing in archival footage, participants include Yoko Ono, Fab 5 Freddy, Bill T. Jones, and Keith’s parents, Joan and Allen Haring.

4 A League Of Their Own (1992) 78%

In Penny Marshall’s sports comedy about the first female professional baseball organization, Madonna plays the sexually-liberated center-fielder Mae Mordabito, aka “All the way Mae.”

RELATED: 10 Hidden Things Everyone Missed In A League Of Their Own

The crux of the drama centers on Dottie Hinson (Geena Davis), star catcher and team captain of the Rockford Peaches, one of four all-female baseball teams. Along with her kid sister Kit (Lori Petty), Dottie leads her team to the championship game with the help of drunken manager Jimmy Dugan (Tom Hanks).

3 Unzipped (1995) 80%

In the 1995 documentary Unzipped, the work of high-fashion designer Isaac Mizrahi is chronicled in great detail ahead of his 1994 autumn collection rollout. Several high-profile fashionistas appear in the film, including Madonna, Naomi Campbell, Cindy Crawford, Helena Christensen, and more.

For his work, director Douglas Keeve earned an Audience Award for Best Documentary at the 1995 Sundance Film Festival. The film shared the honor with Ballot Measure 9.

2 Desperately Seeking Susan (1985) 83%

Madonna’s first starring role on the big screen came in the 1985 musical rom-com Desperately Seeking Susan, directed by Susan Seidelman.

Co-starring Rosanna Arquette in a Golden Globe-nominated performance, the film follows Roberta Glass (Arquette), an unhappy housewife in the suburbs who spontaneously responds to a personal ad in the newspaper. Her response leads her to bustling New York, where she has an accident in the street that leaves her with amnesia. When she awakes, Roberta finds herself mistaken for Susan (Madonna), a cool city girl with a unique fashion sense.

1 Madonna: Truth Or Dare (1991) 87%

Madonna’s candid sexuality is on full display in the 1991 documentary Truth or Dare, an explicit account of her controversial 1990 tour Blonde Ambition.

The globetrotting doc spans from Japan to Detroit and Canada as Madonna exposes her daily routine ahead of a global music tour. The artist’s personal and professional life is detailed in vivid fashion, with several of Madonna’s band members, backup singers, and dancers weighing in. Despite portraying herself in the film, Madonna received a Razzie nomination for worst actress in 1992. In 2012, the film was nominated as Best Documentary at the 20/20 Awards.