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.
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.
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 Susanused 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.
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.”
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.
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 Stonein 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.”
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.
7. “Live to Tell” (from ‘True Blue,’ 1986)
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.”
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 democratising 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.
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.”
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.
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.
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.”
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.
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.”
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.
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 onNightline 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.”
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
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.”
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.”
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.”
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.”
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.
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.”
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.”
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.”
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 realised that, you know, groove is everything.”
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.
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.”
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.”
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 VirginTour staple despite never being released as a single.
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.”
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.”
34. “4 Minutes” (from ‘Hard Candy,’ 2008)
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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.”
35. “Lucky Star” (from ‘Madonna,’ 1983)
With its shimmery synth intro and an inspired double-entendre about a lover’s “heavenly body,” “Lucky Star” makes for the perfect opening track on Madonna’s first album. She originally wrote the tune for Mark Kamins – the New York club DJ who produced her first single, “Everybody” – in the hope he’d play it in his sets at Danceteria. After recording an R&B-leaning demo with Reggie Lucas, she turned to Jellybean Benitez for guidance. He in turn polished it off with a funky, jittering guitar line. After MTV put the song’s video in rotation, hair ribbons and cut-off gloves became a must-have teenage fashion.
36. “Hanky Panky” (from ‘I’m Breathless,’ 1990)
On her Blond Ambition Tour in 1990, Madonna said of “Hanky Panky,” “You may not know this song, but you know the pleasures of a good spanking.” She based this jazzy ode to the rough stuff on a line from Breathless Mahoney, the character she played in the film Dick Tracy (“You don’t know if you want to hit me or kiss me”). “Some girls, they like candy, and others, they like to grind,” she sang. “I’ll settle for the back of your hand somewhere on my behind.” For Madonna, the concept was tongue-in-cheek. When some people took her seriously, she shot back, “Try it and I’ll knock your fucking head off.”
37. “Deeper and Deeper” (from ‘Erotica,’ 1992)
“Deeper and Deeper” is a house-flavored track complete with a reference to Madonna’s soon-to-be dance-floor classic “Vogue” – “Let your body move to the music,” she sings. “We got to that point, and we’re like, ‘What the hell. Let’s have fun with it,'” producer Shep Pettibone recalled. Pettibone, who also produced “Vogue,” wasn’t as excited about Madonna’s request to throw in a flamenco guitar solo midway through the track but acquiesced to the woman in charge: “I didn’t like the idea of taking a Philly house song and putting ‘La Isla Bonita’ in the middle of it. But that’s what she wanted, so that’s what she got.”
38. “Keep It Together” (from ‘Like a Prayer,’ 1989)
“Family is everything. Family comes first,” Madonna once said. “It’s not what I expected it to be, but nothing ever is.” 1989’s Like a Prayer had heavy meditations on this theme like “Promise to Try” and “Oh Father.” This more upbeat track recalls Sly and the Family Stone’s “Family Affair” and Sister Sledge’s “We Are Family,” with Madonna singing, “Brothers and sisters hold the key… Don’t forget that your family is gold.” She called “Keep It Together” a tribute to Sly, adding, “The overall emotional context of the album is drawn from what I was going through when I was growing up – and I’m still growing up.”
39. “Bitch I’m Madonna” (from ‘Rebel Heart,’ 2015)
Thirteen albums into her career, Madonna issued the ultimate kiss-off: a frantic, grinding jam stocked with tempo changes and attitude for days. Many songs on 2015’s Rebel Heart react to ageism and sexism in the music industry. “Women, when they reach a certain age, have accepted that they’re not allowed to behave a certain way,” she told Rolling Stone. “But I never follow the rules. I never did, and I’m not going to start.” Diplo produced the track and Nicki Minaj contributed a biting rap. “It’s a back-and-forth until she gets it right,” Madonna said of teaming with Minaj. “It’s a total collaboration.”
40. “La Isla Bonita” (from ‘True Blue,’ 1986)
“La Isla Bonita” was unlike anything Madonna had recorded before, a Latin-tinged uptempo ballad complete with Spanish guitar, Cuban percussion and lyrics that explored dreams of exotic San Pedro. Madonna wrote the song with Patrick Leonard and Bruce Gaitsch. “She’s very good at finding a lyrical theme that fits the mood of the music,” Leonard recalled. He originally penned “La Isla Bonita” for Michael Jackson (whom he’d previously worked with on the Jacksons’ Victory tour and album). But Jackson didn’t like the title, so Leonard tried it out on Madonna, who tailored the lyrics to fit her own idea of “the beauty and mystery of Latin American people.” “I don’t know where that came from,” she told Rolling Stone years later, in reference to the song’s specific imagery. “I don’t know where San Pedro is. At that point, I wasn’t a person who went on holidays to beautiful islands. I may have been on the way to the studio and seen an exit ramp for San Pedro.” The video, in which she played a flamenco dancer, was one of her most theatrical Eighties clips, and its drama has impacted many of her inheritors – Lady Gaga famously ripped it off for her 2009 hit “Alejandro.”
41. “Everybody” (from ‘Madonna,’ 1983)
When Madonna handed her friend Mark Kamins her cheaply recorded four-song demo one night at New York’s Danceteria, one song immediately grabbed him. “She brought [‘Everybody’] up to the booth,” Kamins recalled. “I listened to it, played it and got a great reaction.” The song ended up getting her a contract with Sire Records. As Sire president Seymour Stein remembered, “I was in the hospital, hooked up to a penicillin drip. I listened to ‘Everybody,’ and I loved it. It was a deal for three singles and an option for albums afterward. I would have gone down to the bank and withdrawn my own money to sign her if I had to.”
42. “Bad Girl” (from ‘Erotica,’ 1992)
“Bad Girl” is a somber, guilt-ridden ballad sung from the perspective of a woman pursuing a series of unsatisfying one-night stands: “Drunk by six/ Kissing someone else’s lips,” she sings. “I’m not happy when I act this way.” Cowriter and producer Shep Pettibone later recalled how amazed he was at Madonna’s ability to write and record quickly: “Madonna has an incredible mind. She locks the melody into her head and memorizes the words immediately. Madonna’s stories were getting a lot more serious and intense, driving the creative direction of the songs into deeply personal territory.”
43. “Ghosttown” (from ‘Rebel Heart,’ 2015)
This lush standout from Rebel Heart is about sticking with a partner after civilisation has fallen apart. “At the end of the day, if we run out of oil and we don’t have electricity and we don’t have all the modern conveniences, and we have no phones and computers, all we’re going to have is each other,” Madonna said. “That song’s about recognising that.” She wrote the track in three days with a team that included Sean Douglas (the son of actor Michael Keaton), whose work on the 2014 Jason Derulo hit “Talk Dirty” had caught Madonna’s ear. “I basically checked it off my life bucket list,” Douglas said.
44. “Hollywood” (from ‘American Life,’ 2003)
After a pair of well-received albums (1998’s Ray of Light and 2000’s Music), 2003’s American Life was an artistic and commercial disappointment. Still, nobody could deny the power of “Hollywood,” where an acoustic-guitar riff locks into a strict beat as Madonna sings about the pleasures and pains of America’s dreamiest city. “Hollywood,” Madonna mused on the set of the song’s video, is “the city of dreams, the city of distraction, the city of superficiality. It’s the place to go get distracted from what’s really important in life. And you can lose your memory… You can lose everything. You can lose yourself.”
45. “This Used to Be My Playground” (from ‘Barcelona Gold,’ 1992)
Madonna co-starred with Tom Hanks and Rosie O’Donnell in the baseball movieA League of Their Own and penned this darkly sentimental song for its soundtrack. She threw it together in two frenzied days toward the end of the sessions for 1992’s Erotica – coming up with the melody by humming over computer-generated chords and rewriting a string arrangement while an orchestra waited patiently in the studio. The song became a huge hit, breaking her tie with Whitney Houston to become the female singer with the most Number One singles at the time.
46. “Papa Don’t Preach” (from ‘True Blue,’ 1986)
“Papa Don’t Preach” was the only song on True Blue that Madonna didn’t have a significant hand in writing. “When I first heard this song, I thought it was silly,” she told The New York Times. “But then I thought, ‘Wait a minute, this song is really about a girl…[who] has a very close relationship with her father and wants to maintain that closeness.’ To me, it’s a celebration of life.” Though conservatives tried to grasp onto the song as a pro-life anthem, Madonna was clear it was all about a woman’s autonomy. “Ronald Reagan is one papa who shouldn’t preach,” she told Rolling Stone in 1987.
47. “Bedtime Story” (from ‘Bedtime Stories,’ 1994)
Icelandic pop innovator Björk has long been a Madonna fan. “I’m not going to get into the things she’s done for women,” Björk told Rolling Stone in 1994. “You’d fall asleep, there are so many.” She wasn’t sure how to approach her contribution to Bedtime Stories: “I couldn’t really picture me doing a song that would suit her. But on second thought, I decided… to write the things I’ve always wanted to hear her say.” What emerged was an atmospheric, house-tinged exploration of feelings so powerful they transcend language – “Traveling, leaving logic and reason,” Madonna sings. It helped pave the way for future EDM experiments.
48. “Me Against the Music” (from ‘In the Zone,’ 2003)
Madonna and Britney Spears made history when they kissed at the 2003 MTV Video Music Awards. But they did more that night than merely swap spit: Spears played the Queen of Pop a new song from her upcoming LP, In the Zone, and Madonna offered to make it a duet. Cowritten by The-Dream and Tricky Stewart, “Me Against the Music” is a propulsive ode to dance-floor revelation with a beloved music video in which the singers tussle and taunt each other with impressive gymnastic moves.
49. “Act of Contrition” (from ‘Like a Prayer,’ 1989)
The final song on “Like a Prayer” is the perfect way to cap off one of the most Catholic albums ever. Over a searing (uncredited) Prince solo and a backward tape loop of the Andraé Crouch Choir’s performance on “Like a Prayer,” Madonna recites the Roman Catholic prayer of confession and repentance – which just happened to be in her head at the time. “That was totally conceived of in the studio,” she said. “I just started fooling around. Whatever was in my head. It’s totally unedited.”
50. “Die Another Day” (from ‘Die Another Day,’ 2002)
Madonna made a cameo as Pierce Brosnan’s saucy fencing instructor in the James Bond flick Die Another Day and recorded its theme song. Madonna and Mirwais brought in French composer Michel Colombier after MGM execs told them to make their demo more in line with the Bond vibe. Colombier went in a “film-score-esque” direction. “Sixty real strings, played live, became audio files in his computer,” said Colombier, “chopped like pieces of fabric.” It was the biggest Bond theme in ages.
