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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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34

“4 Minutes” (from ‘Hard Candy,’ 2008)

Madonna’s 2008 album Hard Candy saw her return to the sexually charged pop of her earlier days. After years of working with producers from the world of dance music, she collaborated with R&B and hip-hop stars like Timbaland, Pharrell Williams and Kanye West. “They’re good,” she said, “and I like their shit.” The album’s raucous, Timbaland-helmed lead single paired her alongside Justin Timberlake for a marching-band-led throwdown with an insistent “tick-tock-tick-tock-tick-tock” refrain. “It’s kind of a funny paradox, like we’re saying, ‘We’re running out of time – people, wake up,'” Madonna said. “‘But if we are going to save the world, can we please have a good time while we’re doing it?'” The singer was focused on raising awareness for children in Malawi, and she clicked with Timberlake when the two started sessions by “talking about something we cared about.” The result: a track that’s half protest song, half party. “I like his phrasing when he writes music,” Madonna said of Timberlake. “I like his approach. He’s playful but at the same time really professional.” Said Timberlake of working with Madonna, “We went down into the valleys together and we came out on top of mountains.”

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33

“True Blue” (from ‘True Blue,’ 1986)


From its quaint shuffle rhythm and its twinkling chimes to its charming video, "True Blue" found Madonna sounding blissfully smitten. At the time, she was. The singer had married Sean Penn the year before, and she named this girl-group-steeped song (and the album it appeared on) after a favorite expression of Penn's. By the end of the Eighties, Madonna would both divorce Penn and stop performing the song in concert, but she still looked back at it fondly; in 1998, when an interviewer asked her what the words "true blue" reminded her of, she answered, "Romance."

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32

“I Deserve It” (from ‘Music,’ 2000)


According to Madonna, "I Deserve It" is a love song, but a lonely one. The curiously earnest Music track couples searching lyrics with acoustic strumming and increasingly dissonant keyboards. "The juxtaposition of the acoustic guitar and then that synth siren sound, to me, that strange combination makes it a little bit uncomfortable," she said. But what makes the tune a standout is Madonna's vocals, which producer Mirwais chose to leave unsullied by digital processing. "At first, I was disturbed because I hadn't done that in a long time," Madonna said. "But then I started to see the purity of it."

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31

“Gambler” (from ‘Vision Quest,’ 1985)

Madonna recorded two songs for the 1985 flick Vision Quest – "Crazy for You" and this urgent-sounding dance track. She'd written the song herself and recorded it with Jellybean Benitez around the time her debut album was being released. The song's assertive feel jelled well with the movie's theme, especially the story of its hard-to-get heroine (played by Linda Fiorentino). "'The Gambler' is really the girl's point of view, because she's, like, an unstoppable person," Madonna said. "She doesn't really need this guy." Offscreen, it became a Virgin Tour staple despite never being released as a single.

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30

“Take a Bow” (from ‘Bedtime Stories,’ 1994)

Madonna ended Bedtime Stories in grand style with this Shakespeare-quoting ballad, in which she tells a no-good lover, "Take a bow, the night is over/The masquerade is getting older." Madonna wrote the song with Kenneth "Babyface" Edmonds, then on a roll thanks to R&B hits by TLC and Toni Braxton. "She came to me for lush ballads, so that's where we went," Edmonds recalled years later. "I wasn't so much thinking about the charts. I think I was more in awe of the fact that I was working with Madonna. It was initially surreal. Then you get to know the person a little bit and you can calm down."

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29

“Frozen” (from ‘Ray of Light,’ 1998
)

Cold and cinematic, the electro-inflected ballad "Frozen" was designed to express Madonna's feelings of "retaliation, revenge, hate [and] regret." She had drawn inspiration from the 1990 Debra Winger movie The Sheltering Sky, about a couple attempting to save their marriage during a difficult trip in North Africa. The film informed both the song's love-under-pressure theme and its Moroccan-influenced beats. As she wrote it, Madonna became so entranced that her original demo stretched to 10 minutes. In the video, filmed in California's Mojave Desert, she strove to portray the "embodiment of female angst."

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28

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

"Cherish" is one of Madonna's most optimistic love songs, a tune about a romance inspired by Romeo and Juliet's. By her own account, it came from a pure place. "[I wrote it] in a superhyper-positive state of mind that I knew was not going to last," she said. The tune itself had staying power, making it to Number Two, thanks in part to a sleek, playful video directed by fashion photographer Herb Ritts. The success of "Cherish" surprised Madonna. "The songs that I think are the most retarded songs I've written, like 'Cherish'… end up being the biggest hits," she once said.

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27

“Don’t Tell Me” (from ‘Music,’ 2000)

Madonna surprised listeners with this twangy take on electro pop. But the song originated in another genre entirely. "Don't Tell Me" began as a tango written by her brother-in-law, singer-songwriter Joe Henry, that Madonna and French producer Mirwais reworked during sessions in London for Music. The singer says she was initially drawn in by "the sentiment of it, the defiance, the attitude of it – 'Don't tell me to stop,'" she said. "Just loved that." In talking about the differences between his version and hers, Henry said, "I realized that, you know, groove is everything."

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26

“Beautiful Stranger” (from ‘The Spy Who Shagged Me,’ 1999)

In 1993, Madonna told actor Mike Myers, "We should do a remake of Some Like It Hot, only with you and Garth playing the Tony Curtis/Jack Lemmon parts. Sharon Stone should play the Marilyn Monroe part, and I'm gonna play the bandleader." That never came to pass. But Madonna did end up recording a hit for the soundtrack to 1999's Austin Powers sequel, The Spy Who Shagged Me. Madonna and producer William Orbit married the electronica of Ray of Light and Sixties psych-pop. Introducing the video on the U.K. show Top of the Pops, she gave the song a simple review: "It's groovy, baby."

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25

“Where’s the Party” (from ‘True Blue,’ 1986)

“I want to free my soul,” Madonna sang on “Where’s the Party,” an ode to weekend good times that recalled the energetic escapism of “Everybody” and “Holiday.” It might’ve seemed a little like a light afterthought on True Blue, amid ambitious songs like “Papa Don’t Preach” and “La Isla Bonita.” But it had a deeper meaning, serving as a veiled response to her mean-spirited press coverage. Speaking with The New York Times around the release of True Blue, she called the song “my ultimate reminder to myself that I want to enjoy life and not let the press get to me, because every once in a while it does.”

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24

“Physical Attraction” (from ‘Madonna,’ 1983)

This flirty early track offered a subtle suggestion of the more provocative statements she had in store. "Physical Attraction" was the killer B-side to "Burning Up," a Number Three dance hit that promised huge potential for Sire Records' new signee. "Reggie [Lucas] wrote two of the songs: 'Borderline' and 'Physical Attraction,'" recalled Sire's Michael Rosenblatt. "The rest were Madonna songs." Lucas summed up the freedom of those early sessions: "There was no committee rendering judgment from on high," he said, "because she was brand new and frankly nobody cared about her that much."

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23

“Who’s That Girl” (from ‘Who’s That Girl,’ 1987)

When Madonna needed music for her third movie, tentatively titled Slammer, she quickly came up with a hit. “I had this chorus,” co-writer Patrick Leonard recalled. “She went in the back room with a cassette of that. I worked out the rest of the parts and she finished the melody and the lyrics. She said, ‘We’ll call it “Who’s That Girl,” and I think that’s a better title than Slammer, so we’ll change the title of the movie, too.'” Loosely based around her character in Who’s That Girl (“feisty femme” Nikki Finn), the song is a bright dance-popper that fared much better than the lackluster film it was tied to.

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22

“Holiday” (from ‘Madonna,’ 1983)

Madonna was nearing the final stages of production on her debut album when Sire Records A&R rep Michael Rosenblatt decided it needed one more surefire pop song. "Something much more uptempo," he recalled. "I needed to get more money to finish the record. So [Sire president] Seymour [Stein] said, 'Take her down to L.A., have her meet the executives at Warner Bros.' Once she got out to L.A., everybody started buzzing." After securing the $10,000 he needed to finance the new track, Rosenblatt returned to New York, where he met with Madonna's co-producers Jellybean Benitez and Reggie Lucas, telling them, "Whoever comes up with an uptempo dance song gets to produce it." Three days later, Benitez brought him "Holiday." Written by Curtis Hudson and Lisa Stevens of the group Pure Energy, and revamped by Benitez and Madonna (who played cowbell on it), "Holiday" was first released as the B-side to a 12-inch version of "Lucky Star," serviced to club DJs. It would soon become Madonna's first Top 20 single. "I knew that as soon as DJs saw John 'Jellybean' Benitez on the 'Holiday' side, that was it," Benitez recalled, "because DJs stick together."

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21

“Human Nature” (from ‘Bedtime Stories,’ 1994)

"The song is basically saying, 'Don't put me in a box, don't pin me down, don't tell me what I can and can't say,'" Madonna said of this pointed response to conservative scolds. "It's about breaking out of restraints." The lyrics directly take on the media firestorm Madonna started with her Erotica album and tour and her 1992 photo book, Sex. "Did I say something wrong?/Oops, I didn't know I couldn't talk about sex," she sings matter-of-factly. Musically, the song is a foray into hip-hop and R&B, sampling a jazzy beat from Main Source and biting some vocal phrasing from A Tribe Called Quest's "Electric Relaxation."

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20

“Drowned World/ Substitute for Love” (from ‘Ray of Light,’ 1998)

Between 1994’s Bedtime Stories and 1998’s Ray of Light, Madonna became a mother, giving birth to her daughter Lourdes. She addressed that life-changing moment on Ray of Light‘s opening track, a ballad exploring epiphanies about fame and family. “I got pregnant, and the whole idea of giving birth and being responsible for another life put me in a different place,” she said in 1998. “People have been obsessed with the idea that I am always reinventing myself, [but] I’d rather think that I’m slowly revealing myself.”

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19

“What It Feels Like for a Girl” (from ‘Music’, 2000)

Guy Ritchie's violent video for this woozy track was Madonna's second clip to be banned by MTV. The song opens with a clip of singer-actress Charlotte Gainsbourg's meditation on gender from the 1993 film The Cement Garden, making Madonna's point crystal-clear. "Our generation has been encouraged to grab life by the balls, be superindependent," Madonna said in 2001, "and I realized that smart, sassy girls who accomplish a lot are really frightening to men… That's also what that song is about: swallowing that bitter pill."

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18

“Angel” (from ‘Like a Virgin,’ 1984)

“I think it’s important to call angels to you to protect you,” Madonna once said. “That’s part of the ritualistic moment. The calling of angels.” That side of Madonna’s Catholicism came out on the third single from Like a Virgin, an ode to a heavenly love “full of wonder and surprise” complete with the sound of her giggling voice on the intro. “Angel” began as a demo written with Stephen Bray. When it was released, Madonna chose not to shoot a video for the song (probably because so many of her other videos were still in heavy rotation at the time), but Sire Records created one by stitching together bits of existing clips

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17

“Justify My Love” (from ‘The Immaculate Collection,’ 1990)

With its spare, submerged groove (based around a Public Enemy sample) and breathless vocal, "Justify My Love" is one of Madonna's most understated hits. The song was written by Lenny Kravitz and Prince-collaborator Ingrid Chavez, who culled most of the original lyrics from a love letter she wrote (but didn't mail) to Kravitz. When MTV banned its dreamy, erotic video, Madonna went on Nightline to explain her intentions. "We're dealing with sexual fantasies," she said. "And being truthful and honest with our partner, and these feelings exist. I'm just dealing with the truth here."

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16

“Open Your Heart” (from ‘True Blue,’ 1986)

"Open Your Heart" was originally a rock tune called "Follow Your Heart" by songwriters Gardner Cole and Peter Rafelson, who intended the song to be recorded by Cyndi Lauper. The Temptations were also in the running to cut the track. "The original didn't fit what Madonna was doing at the time," Cole recalled. But Madonna and Patrick Leonard flipped the arrangement, added a bass line and turned it into a quintessential clipped-beat Eighties dance-pop jam. Hooked to a stunning peep-show-themed video, "Open Your Heart" became Madonna's third Number One single off True Blue.

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15

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


The PG-rated fifth hit off of Like a Virgin is a snappy love pledge that might be Nile Rodgers' funkiest production on the album, was mystifyingly flagged, alongside W.A.S.P.'s "Animal (Fuck Like a Beast)," in 1985 by the media watchdog group Parents Music Resource Center in its "Filthy Fifteen." The song became a style anthem for a generation of young Madonna wannabe's. You can see them in the song's video – a live performance from The Virgin Tour – a pop army in lace gloves and shades. As Rodgers wrote in his memoir: "In a low-res world, she was high-definition hyperrealism."

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14

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


A piano ballad with a lush string backdrop, Madonna's great tearjerker was written (with help from wingman Patrick Leonard) about her mother, Madonna Fortin Ciccone, who died of breast cancer when her daughter was five years old. "Little girl don't you forget her face/Laughing away your tears/When she was the one who felt all the pain," Madge sings, channeling multiple voices. "It's my father talking to me," she said in 1989, and "it's me talking to me." The song soundtracks Madonna's visit to her mom's grave in Truth or Dare, and remains her most vulnerable emoting on record.

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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 o