Madonna's 50 Greatest Songs - Rolling Stone
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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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13

“Material Girl” (from ‘Like a Virgin,’ 1984)

Madonna didn’t write the song and in time didn’t feel it represented her (“I am not a materialistic person…[things] are not mandatory for my happiness,” she told Rolling Stone in 2009). But she liked its gawky swagger, which, combined with producer Nile Rodgers’ clipped, New Wave robo-funk sheen, equaled another major chart hit. “I didn’t think ‘Like a Virgin’ was going to be the song that did it for us,” recalled Rodgers. “I thought it was going to be ‘Material Girl.’ ‘Material Girl’ to me was cool, and to this day what do people call Madonna? They call her the Material Girl. They don’t call her the Virgin.”

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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."

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7

“Live to Tell” (from ‘True Blue,’ 1986)

"Live to Tell" introduced a new side of Madonna – a moody, confessional ballad, with an unconventional structure and a haunting lyric about a woman living with traumatic secrets she has to hide. "Live to Tell" was unlike anything else she'd written; she composed the lyrics to co-writer Patrick Leonard's track quickly and recorded the vocal in one take. The unorthodox song seemed like commercial suicide when it was released as the lead single from True Blue. But all her risks were validated when it became her third Number One hit. Fans had different interpretations of the chorus: "Hope I live to tell the secret I have learned/ Till then it will burn inside of me." Was it about a breakup? Some kind of sexual abuse? But Madonna wasn't telling. "I could say that 'Live to Tell' was about my childhood, my relationship with my parents, my father and my stepmother. But maybe not. It could be about something in an F. Scott Fitzgerald novel or a story that I heard once. It's true, but it's not necessarily autobiographical."

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6

“Hung Up” (from ‘Confessions on a Dance Floor,’ 2005)

"My first album was a total aerobics record," Madonna declared in 1985. "I make records with aerobics in mind." Twenty years later, she was still on top of the aerobics-disco game – "Hung Up" remains one of her most seductive and surprising hits, a pure-energy workout coming long after the point where most people had begun expecting her to coast. Like the rest of her 2005 album, Confessions on a Dance Floor, "Hung Up" was recorded in the two-room London apartment of producer Stuart Price, reviving the stripped-down electro-sleaze momentum of her earliest records. For the coup de grâce, "Hung Up" samples a long-forgotten synth hook from deep in the ABBA catalog – their 1979 Eurodisco cashin, "Gimme! Gimme! Gimme! (A Man After Midnight)." Her voice gets looped until she sounds like an out-of-breath party commando. "Time goes by so slowly," Madonna chants over the spedup ticking-clock sound effects – but the whole song is a dance-floor time warp.

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5

“Like a Virgin” (from ‘Like a Virgin,’ 1984)


Even if the word "virgin" is the only sexual reference in the lyrics, "Like a Virgin" still sounds saturated in lust – it's all in the way Madonna sings it over that Nile Rodgers funk throb. The song was written by Billy Steinberg and Tom Kelly, who were told they might have to change the title to get it recorded. But Madonna loved it. ("They're so geeky, they're cool," she said of the lyrics.) She gave "Like a Virgin" a memorable debut at the 1984 MTV Video Music Awards, a moment as indelible as the Beatles on Ed Sullivan – the song is forever linked with the image of Madonna, in a wedding gown, brazenly humping the stage. "I was surprised with how people reacted to 'Like a Virgin,'" Madonna told Rolling Stone in 1987, perhaps a tad disingenuously. "Because when I did the song, to me, I was singing about how something made me feel a certain way – brand-new and fresh – and everyone else interpreted it as, 'I don't want to be a virgin anymore. Fuck my brains out!' That's not what I sang at all."

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4

“Borderline” (from ‘Madonna,’ 1983)

In March 1984, Madonna went with producer Nile Rodgers to see Duran Duran at Madison Square Garden, where she sat in the audience unrecognized. A few months later, she was headlining. "Borderline" was the reason why – the breakthrough hit propelled her from urban-radio contender to pop queen. She made "Borderline" with R&B writer-producer Reggie Lucas while she was apartment-sitting for artist Jean-Michel Basquiat. Lucas, a jazz cat who played guitar on Miles Davis' Dark Magus, wasn't fazed by Madonna's boho-punk style. "She wasn't the weirdest person I'd ever met, you know?" he said. "I'd worked with Sun Ra! So after hanging out with the Heliocentric Worlds of Sun Ra, Madonna didn't seem particularly avant-garde." "Borderline" mixed up various styles of downtown cool to become Madonna's first Top 10 hit, and its video (an interracial love story filmed in Los Angeles) offered MTV viewers a key lesson in early-Madonna style. For a nightly highlight of her 2008 tour, Madonna picked up an electric guitar to crash out a punk rock version.

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3

“Vogue” (from ‘I’m Breathless,’ 1990)


When the late Lauren Bacall died in 2014, it was a sad day for Madonna fans – Bacall was the last surviving star name-checked in "Vogue." The 1990 smash is Madonna's most audacious manifesto, a roll call of old-school Hollywood glam with lavish house beats that went to Number One in over a dozen countries. She celebrates the politics of dancing, where anyone can become a star just by striking a pose, because "beauty's where you find it." "Vogue" pays tribute to New York's gay ball culture (later famed around the world via the classic 1991 documentary Paris Is Burning). As she told Rolling Stone years later, "I was going to Sound Factory and checking out these dancers who were all doing this new style of dancing called 'voguing.' And Shep Pettibone, who co-produced 'Vogue' with me, used to DJ there." She didn't soft-pedal the political provocation of such an explicitly pro-queer song in the Reagan-Bush "Silence = Death" years – that autumn she turned "Vogue" into a Rock the Vote ad, with new lyrics: "Dr. King, Malcolm X, freedom of speech is as good as sex."

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2

“Into the Groove” (Non-album single, 1985)


"Into the Groove" is the streetwise beatbox anthem Madonna kept trying to write when she was down and out in New York, the days when she squatted and ate out of garbage cans. As she explained in 1985, "It was the garbage can in the Music Building on Eighth Avenue, where I lived with Steve Bray, the guy I write songs with. He's Useful Male #2 or #3, depending on which article you read." Madonna and Bray – the ex-drummer in her punk band – knocked off "Into the Groove" as an eight-track demo. (Bray later said he came up with the "rib cage" and "skeleton" of the music, with Madonna writing lyrics and adding her own touches – in this case, the song's bridge.) Her movie Desperately Seeking Susan used it for the scene where Madonna hits Danceteria, but then it unexpectedly blew up on the radio. It still sounds like a low-budget demo – those breakbeats, the desperate edge in her voice when she drones, "Now I know you're mine" – but that raw power is what makes it her definitive you-can-dance track. "Into the Groove" has ruled the radio ever since.

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1

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

Ever since her early days, Madonna has been obsessed with the taboo connection between sex and spirituality. She tapped into that idea for her greatest song, the 1989 gospel-disco smash "Like a Prayer." When Madonna testifies, "I'm down on my knees/I wanna take you there," she could be singing about praying or oral sex or – most likely – both. As she told Rolling Stone at the time, "I pray when I'm in trouble or when I'm happy. When I feel any kind of extreme." It wouldn't be Madonna's style to drop such a personal song without a huge scandal to go with it. But even by her standards, "Like a Prayer" stirred up some controversy. The song debuted as a soft-drink ad – except the entire ad campaign was instantly torpedoed once the world got a look at the video. It's a cleavage-and-blasphemy cocktail where Madonna visits a Catholic church, has hot sex with a black-saint statue, dances in front of burning crosses and experiences stigmata. Yet somehow, the video is nowhere near as shocking as the song itself – all of Madonna's musical and emotional extremes, packed into five roof-shaking minutes.

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