Madonna: 50 Looks We Can't Forget

As the Material Girl celebrates a half-century, trace her every fashion reinvention. By Aaron Parsley and Cara Lynn Shultz

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AMERICAN GIRL

For the movie The Next Best Thing, which starred Madonna and Rupert Everett, the singer recorded a cover of Don McLean's classic "American Pie." The remake, released in February 2000, would became her first single of the new millennium. The video had a simple concept: an all-American Madonna dancing around with a U.S. flag in blue jeans and a tiara.