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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.

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10

“Burning Up” (from ‘Madonna’, 1983)

Part of a four-song one fateful New York night, this club banger was re-recorded with producer Reggie Lucas and then remixed by Eighties club genius Jellybean Benitez. The upshot is a freestyle electro-jam spiked with horndog rock guitar. "Burning Up" came with a steamy-stylish video in which Madonna writhes in a short skirt and crucifix earrings on a dark suburban road, and ended up scaling the dance charts. "I knew she was gonna be big," Benitez said. "That her album could go gold. I never thought it could go six-times platinum."

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9

“Music” (from ‘Music’, 2000)

After years spent making albums that bridged boundaries of race, gender and sexual orientation, Madonna finally wrote a tune explicitly devoted to the democratizing power of music itself. But her inspiration for this glitchy disco throwdown didn't come from her early days in New York's wild club scene – it emerged at a Sting concert where fans were well-behaved until the musician played old Police hits. "Everyone was practically holding hands… I mean, it really moved me," she told Rolling Stone in 2000. "And I thought, 'That's what music does to people.'" The track, propelled by French dance music producer Mirwais' pounding beat, was a Number One smash, and its video (featuring a little-known Sacha Baron Cohen) showed Madonna skillfully uniting the bourgeoisie and the rebel, even as she was five-and-a-half months pregnant.

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8

“Ray of Light” (from ‘Ray of Light,’ 1998)

Before William Orbit and Madonna began collaborating on her 1998 album, Ray of Light, the producer mailed over a DAT with 13 songs, including an interpolation of Clive Maldoon and Dave Curtiss' Seventies psych-folk epic "Sepheryn." Madonna adjusted the lyrics to capture more of a sense of "wonderment," the feeling of "looking at the world finally with your eyes open… A ray of light to me is hope. We are zooming forward, but that doesn't mean you can lose touch with the spiritual side of things." Sonically, the song was more than just a leap into futuristic electronica – its complex breakbeats, clanging guitars and grooved-out organs were topped with Madonna's most powerfully sung vocals to date, the result of vocal training she'd done for her role in the 1996 movie Evita. "I learned how to sing in a way that I never did before, so it really influenced my songwriting," she said. Said Orbit of working on Ray of Light, "Madonna's production involvement was a major factor in this record, and it's something that shouldn't be overlooked