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Madonna’s 50 Greatest Songs

Definitive guide to more than three decades of dance-pop anthems, confessional ballads and boundary-breaking self-expression

Our list of the Madonna‘s 50 greatest songs is a fitting tribute to the 2008 Rock and Roll Hall of Fame inductee, whose gift to songwriting is matched only by her skill for finding the right partners to unlock her creativity: Prince, William Orbit, Diplo, Justin Timberlake and more. The stories behind Madonna’s songs reveal the evolution of the only artist in the world who’s equally at home in the club, in the church and on the catwalk; there are psychosexual dramas, disco reveries, tear-jerking ballads and pop songs that unite the globe – all by an artist who has never risked making the same album twice. “I don’t think about my old stuff,” she told Rolling Stone in 2015. “I just move forward.” Madonna is as restless as she is relentlessly imaginative – and we just can’t look away.

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12

“Express Yourself” (from ‘Like a Prayer,’ 1989)

Madonna's great girl-power anthem springboards off the Staple Singers' 1971 "Respect Yourself" into Eighties dancepop heaven. Madonna urges ladies to be more assertive with their men ("If you don't say what you want, then you're not going to get it," she testified). It hit Number Two in the U.S., and resulted in the most expensive music video ever made at the time, directed by a young David Fincher. It's a song so iconic, Lady Gaga basically reupholstered it for "Born This Way." "When I heard [it] on the radio… I said, 'That sounds very familiar,'" Madonna quipped. And no surprise, it sounded just as grand.

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11

“Crazy for You” (from ‘Vision Quest’, 1985)

Madonna's second Number One single was a carbonated ballad with propulsive production by Jellybean Benitez. To some, it was a surprise: Upon hearing she'd be recording it, the song's co-writer John Bettis' response was, "Excuse me? Madonna? Really? Can she sing a song like that?" The single was the highlight of the film Vision Quest, soundtracking high school wrestler Matthew Modine falling for art-girl Linda Fiorentino in a perfect reflection of mainstream America falling for arty-underground club kid Madonna Louise Ciccone. The movie even features Madge belting it out in her first screen appearance.