Possessing one of the most distinctive voices in pop music and one of the most distressing résumés on the big screen, Madonna has proven that whatever the role -- screwball seductress, martyred Argentinian first lady, embittered single mom-cum-yoga instructrix -- her abilities as a performer will manage to undermine any production whose credits bear her name. Like Elvis before her, Madonna has proven that no matter how sterling a pop reputation an artist may have, success on the Billboard Top 100 does not translate into similar plaudits at the box office.
Born Madonna Ciccone in Bay City, MI, in 1958, Madonna was raised in a strict Roman Catholic household. She attended the University of Michigan as a dance student for a brief period before dropping out to move to New York City in 1977. There, she quickly became a habitué of various downtown gay discos; spurred on by her dance teacher and her deejay pals, she embarked on a singing career. Before releasing her debut album, however, she made a debut of another kind in an all-but-forgotten, micro-budgeted date-rape melodrama entitled A Certain Sacrifice (1979). In an omen of things to come, Madonna later tried to halt the theatrical release of the film after her musical career took off.
The artist's proper screen debut came courtesy of Susan Seidelman's Desperately Seeking Susan. The 1985 release featured Madonna in a supporting role as a funky girl/object of desire around which the film's screwball plot revolved. Her rising star helped to make Susan a minor hit; aided by Seidelman, she was able to capitalize on her effervescent comic charm and her kooky, uber-Soho, Material Girl persona.
Unfortunately, Madonna's relationship with volatile young actor Sean Penn led her to accept a role opposite him, both in real life as well as onscreen in Shanghai Surprise (1986). The retro-styled, George Harrison-produced debacle endured a brief and mercilessly lambasted life at the box office; Madonna's marriage to Penn didn't last much longer. Next up for the indefatigable entertainer was Who's That Girl? (1987), a stillborn, flimsy imitation of the Melanie Griffith/Jeff Daniels vehicle Something Wild, released just one year prior. Notable only for its hit title track, the ostensible homage to Howard Hawks starred a pained Griffin Dunne opposite a bubbly, impetuous Madonna, apparently performing in the style of her semi-controversial "Open Your Heart" video. Needless to say, their chemistry did little to ignite box-office fireworks.
Madonna's next vehicle was undoubtedly her most high profile to date; cast opposite Warren Beatty in Dick Tracy (1990), she received lavish amounts of pre-film hype, particularly as she was involved at the time with long-in-the-tooth, alpha-stud Beatty. However, the much-anticipated feature failed to make good on the promise that surrounded its production, and Madonna herself came away with only a few choice Steven Sondheim production numbers to her credit. However, the "inspired by the motion picture" soundtrack album did help spark one of the singer's most enduring cause celebres -- "voguing."
It took director Alex Keshishian to (literally) strip some of the veneer from the Madonna mystique with his tell-all documentary Truth or Dare the following year. The feature's risqué subject matter -- including the songstress' unabashed fellating of an Evian bottle -- created a ratings stink with the MPAA and revealed some previously unexposed dimensions of Madonna's relationship with Beatty, such as his incessant ridicule of her.
Madonna next courted the best reviews of her film career to date playing a feisty baseball player in the 1992 A League of Their Own, in which she starred amongst a talented ensemble cast that included Tom Hanks, Geena Davis, and offscreen gal-pal Rosie O'Donnell. Those favorable reviews were soon overshadowed, however, by the maelstrom of negative publicity just a few months later, when she formed a troika of artistic shame with her starring role in the pseudo-S&M thriller Body of Evidence (1993), her show-and-tell photo book Sex, and her subpar dance album Erotica.
Madonna kept a relatively low profile during the next three years, popping up occasionally for cameos in Blue in the Face and Four Rooms as well as a leading part in Abel Ferrera's barely-released Dangerous Game, co-starring Harvey Keitel. Instead, she spent much of her free time hounding director Alan Parker to cast her in the title role of the long-gestating film version of Andrew Lloyd Weber's Evita. Madonna's efforts eventually paid off when she won the part in the Christmas 1996 release; although critics responded with mixed opinions, the singer/actress managed to garner a Golden Globe for her performance.
Just when it seemed the actress had written off Hollywood for good, fate came calling in the form of boy-toy gal pal Rupert Everett and his script idea titled The Next Best Thing. Billed as a romantic comedy, the John Schlesinger-helmed vehicle was in actuality an uneasy melange of The Object of My Affection, My Best Friend's Wedding, and, improbably, Kramer vs. Kramer. Critics responded to the film with primal screams of derision, many of which were aimed at Madonna's balsa wood-inspired and deeply schizophrenic performance. Around this time, insult was indeed added to injury when, in early 2000, the erstwhile thespian was dubbed the Worst Actress of the Century at the Razzie Awards, beating out such notables as Bo Derek, Pia Zadora, and Elizabeth Berkley.
The stage was set for another of the actress' many career reinventions, and it seemed as though she might do just that with her marriage to film director Guy Ritchie, the father of her second child, Rocco. Though she had not yet appeared in one of the Brit's testosterone-laden heist films (including 1998's Lock, Stock, and Two Smoking Barrels and 2000's Snatch) she did play a starring role in their lavish Scottish Highlands' nuptials in December of 2000.
It wouldn't be long before Madonna collaborated artistically with her new beau. Subscribing to the age-old Hollywood dictum that a couple can't truly be in love without an accompanying vanity project, the Material Girl and Ritchie dusted off Italian director Lina Wertmuller's 1974 post-feminist chestnut Swept Away... By an Unusual Destiny in the Blue Sea of August for a lavish remake, albeit one without the original film's rape scene and communist subtext. Though many reviewers pointed out Madonna's natural adeptness at portraying a spoiled, shrewish heiress who engages in dominant/submissive sex games with a lusty Italian seaman, they were less convinced of the positive emotional "transformation" her character underwent over the course of the film. True to form, audiences avoided Swept Away like the plague, as it struggled to crack seven digits at the box office, making it one of the least-profitable films of 2002. In March of 2003, the Razzie Awards responded in kind, showering Swept Away and its star with 5 wins including Worst Picture of the year. Unfortunately, Madonna had to share her award for Worst Actress with her acolyte, another pop star trying to segue into film, Britney Spears.
Madonna would continue to work in film, making her directorial debut 2008 with the indie film Filth and Wisdom and following this up with the period biopic W.E. in 2012.