Madonna Movies: From Best to Worst (Yes, There Are Some Best)

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'W.E.,' the highly anticipated Wallis Simpson biopic directed by Madonna, is about to make its North American debut at the Toronto International Film Festival -- and much like most of her previous film work, it's not exactly 'Citizen Kane.' At best, Madge's film career is a perplexing beast. As a pop star, her talent is undeniable. But disaster seems to strike once the material girl touches a script. With few exceptions, her cinematic forays have been uniformly ill-advised and critically savaged. 'W.E.' took a beating at the Venice Film Festival earlier this month and, if early reviews are any indication, the film is about to get similar treatment on this side of the pond. In anticipation of the critical bloodbath to come, we bring you this look at Her Madgesty's hit-and-miss history on the silver screen.

'Desperately Seeking Susan'

The Best

Things began promisingly enough for Miss Ciccone. With only two credits to her name, Madonna earned a starring role in this madcap comedy that was named one of the ten best movies of 1985 by The New York Times, earned co-star Rosanna Arquette a Golden Globe nomination for Best Actress and has become a prime example of feminist cinema in film schools the world over.

'Madonna: Truth or Dare'

The Best

As her pop star self, Madonna truly shines on the big screen. This semi-scandalous and fully entertaining look at 1990's 'Blonde Ambition' tour is often heralded as one of the best music films ever made and remains one of the top 10 grossing docs of all time. Its influence on pop culture can still be seen today, in everything from parodies of the notorious bottle scene to Lady Gaga's recent HBO special.

'A League of Their Own'

The Best

A supporting role amongst a star-studded cast that included Geena Davis, Tom Hanks, Lori Petty and Rosie O'Donnell helped to keep Madonna's Madonna-ness in check in this sentimental favourite about the All-American Girls Professional Baseball League. As "All the Way" Mae Mordabito, she gives viewers just the right dose of charm and cheekiness. She also contributed the heartbreaking 'This Used to Be My Playground' to the soundtrack.

'Evita'

The Middle of the Road

On one hand, this luscious adaptation of Andrew Lloyd Webber's musical received largely positive critical attention and even scored Madonna a Golden Globe for her work. On the other, it does mark the point at which her cultural appropriation skills became so strong that she was almost able to make an historical biopic about Argentinian First Lady Eva Peron somehow all about Madonna, a talent that is perfected in 'W.E.'

'Dick Tracy'

The Middle of the Road

Madonna was so eager to get the part of Breathless Mahoney in then-boyfriend Warren Beatty's pulpy labour of love that she agreed to work for scale. It wasn't the best choice she ever made in pictures, but it was also far from the worst. While the comic book movie failed to live up to its considerable marketing hype, it was praised for its style and writing. Playing Mahoney also gave Madge the chance to perform original numbers by the celebrated songwriter Stephen Sondheim, including the Oscar-winning 'Sooner or Later.'

'Shanghai Surprise'

The Worst

A terrible and infamous film starring a terrible and infamous couple. A dumb plot about a pair of do-gooders stealing opium in 1930s Shanghai is made even worse by its actors, including Madonna's then-husband Sean Penn in a confused and mumbling performance. The pop queen's efforts as a missionary nurse actually earned her first (but certainly not last) Razzie for Worst Actress.

'Body of Evidence'

The Worst

Sort of a poor man's 'Basic Instinct,' 'Body of Evidence' stars Madonna as a stone-cold seductress who seduces her lawyer after she's accused of murdering her millionaire lover. Although the movie tries it's best to be shocking with its graphic love scenes, the only really offensive thing about it is its weak story and even weaker acting. 'Body' was bad enough to garner Madonna her third Razzie for Worst Actress. She would go on to win Worst Actress of the Century at the 1999 edition of the awards.

'The Next Best Thing'

The Worst

Madonna stars as Abbie, a woman who gets pregnant with her gay best friend's baby after a one-night stand in this well-intentioned but tone-deaf dramadey about a custody battle. The film was, once again, savaged by critics, with our beleaguered actress shouldering much of the blame. It was enough to earn Madonna her fourth trophy for Worst Actress.

'Swept Away'

The Worst

The creative relationship between Madonna and her then-husband Guy Ritchie began promisingly enough with the controversial video for 'What It Feels Like for a Girl,' but all of that danger and mystery disappeared when the two teamed up for a remake of an Italian shipwreck comedy from the '70s. 'Swept Away' swept the 2002 Razzies with wins for Worst Picture, Worst Screen Couple, Worst Remake or Sequel, Worst Director and, yes, Worst Actress. Madonna also picked up a Worst Supporting Actress for 'Die Another Day' that year.

'W.E.'

Madonna's second effort as a writer and director isn't entirely without promise or style, and she could probably make one heck of a music video, but her vision isn't substantial or sustainable enough for a feature-length film. The Wallis Simpson portion of the film is well-acted and semi-capably portrayed, but the modern day half about a Wallis-obsessed woman named Wally is about as deep and elegant as an episode of 'Dawson's Creek' when whatever book the kids are studying in English is shoehorned into a parable about their lives. Worst of all, though, is that 'W.E.' can never totally shake the suspicion that it is actually about another publicly hounded and misunderstood American woman who once married a Brit.