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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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45

“This Used to Be My Playground” (from ‘Barcelona Gold,’ 1992)

Madonna co-starred with Tom Hanks and Rosie O'Donnell in the baseball movie A 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.

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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."

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43

“Ghosttown” (from ‘Rebel Heart,’ 2015)

This lush standout from Rebel Heart is about sticking with a partner after civilization 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 recognizing 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.

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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."

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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.”

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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."

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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."

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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."

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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."

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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."

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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.

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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."