Madonna, inducted into the Rock and Roll Hall of Fame in 2008, stands as a testament to artistic evolution and groundbreaking songwriting. Her genius lies not only in her innate musicality but also in her collaborations with visionaries like Prince, William Orbit, Diplo, and Justin Timberlake. Madonna’s discography is a vibrant tapestry reflecting her chameleonic persona – equally comfortable commanding a dance floor, captivating a church congregation, or owning a fashion runway. Her songs are narratives of psychosexual exploration, euphoric disco nights, heart-wrenching ballads, and global pop anthems, all crafted by an artist who consistently defies repetition. As Madonna herself stated in a 2015 Rolling Stone interview, “I don’t think about my old stuff. I just move forward.” This relentless forward motion, coupled with boundless creativity, ensures Madonna remains an eternally captivating force in music.
“Die Another Day” (from ‘Die Another Day,’ 2002)
Madonna in Die Another Day movie, performing the theme song, highlighting her versatility as a singer and actress.
Madonna’s foray into the James Bond universe with “Die Another Day” showcased her ability to blend into diverse artistic landscapes. Beyond her cameo as a fencing instructor in the Pierce Brosnan Bond film, Madonna, alongside Mirwais, engineered a theme song that became a significant Bond anthem. Initially, MGM executives sought a more traditional “Bond vibe,” leading Madonna and Mirwais to collaborate with French composer Michel Colombier. Colombier steered the track towards a cinematic direction, incorporating “sixty real strings, played live,” which he digitally manipulated to create texture. This fusion of live instrumentation and digital techniques resulted in a Bond theme that resonated with contemporary audiences while maintaining the franchise’s grandeur.
“Act of Contrition” (from ‘Like a Prayer,’ 1989)
Madonna's "Act of Contrition" song from 'Like a Prayer' album, demonstrating her artistic depth and musical experimentation.
Closing out the intensely personal and Catholic-themed album, “Like a Prayer,” “Act of Contrition” serves as a powerful and unconventional finale. Layered with an uncredited, searing guitar solo by Prince and a reversed loop of the Andraé Crouch Choir from the album’s title track, Madonna recites the Roman Catholic prayer of confession and repentance. This spontaneous studio creation emerged from Madonna’s stream of consciousness. “That was totally conceived of in the studio,” she explained. “I just started fooling around. Whatever was in my head. It’s totally unedited.” The track encapsulates the album’s themes of spirituality, introspection, and raw emotion, solidifying its place as a unique entry in Madonna’s song catalog.
“Me Against the Music” (from ‘In the Zone,’ 2003)
Madonna and Britney Spears performing "Me Against the Music" at the MTV VMAs, a iconic duet showcasing Madonna's collaborative spirit.
The 2003 MTV Video Music Awards became legendary not just for Madonna and Britney Spears’ kiss, but also for the genesis of their duet, “Me Against the Music.” Spears played Madonna a track from her upcoming album, In the Zone, and Madonna proposed a collaboration. Co-written by The-Dream and Tricky Stewart, the song is a high-energy dance anthem celebrating the liberating power of the dance floor. The music video, equally iconic, features Madonna and Spears engaging in a playful cat-and-mouse game, showcasing impressive choreography and solidifying the song’s status as a pop culture moment.
“Bedtime Story” (from ‘Bedtime Stories,’ 1994)
Madonna's "Bedtime Story" era, an experimental song highlighting her artistic evolution and Björk collaboration.
“Bedtime Story,” from the album of the same name, marked a significant artistic collaboration with Icelandic innovator Björk. A long-time admirer of Madonna, Björk contributed lyrics that explored themes she felt aligned with Madonna’s persona. “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,” Björk revealed in a 1994 Rolling Stone interview. The result is an ethereal, house-infused track delving into powerful emotions that transcend verbal expression. With lyrics like “Traveling, leaving logic and reason,” the song foreshadowed Madonna’s future explorations into electronic dance music (EDM).
“Papa Don’t Preach” (from ‘True Blue,’ 1986)
Madonna in "Papa Don't Preach" music video, a controversial yet iconic song exploring themes of teenage pregnancy and family relationships.
“Papa Don’t Preach,” a standout track from True Blue, remains one of Madonna’s most debated and impactful songs. Uniquely, Madonna had limited involvement in its songwriting. Initially dismissive, she later connected with the song’s narrative of a young woman’s close bond with her father and her assertion of autonomy. “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.” While conservative groups attempted to interpret it as a pro-life anthem, Madonna emphasized its message of female agency.
“This Used to Be My Playground” (from ‘Barcelona Gold,’ 1992)
Madonna in "A League of Their Own," the movie soundtrack featuring her sentimental song "This Used to Be My Playground".
For the soundtrack of A League of Their Own, where she co-starred with Tom Hanks and Rosie O’Donnell, Madonna crafted the deeply nostalgic “This Used to Be My Playground.” Created in a whirlwind two-day session amidst the Erotica album production, Madonna developed the melody by humming over computer-generated chords and refined the string arrangement with a live orchestra waiting in the studio. The song’s rapid creation belied its significant impact, becoming a major hit and marking Madonna’s record-breaking achievement as the female artist with the most Number One singles at the time, surpassing Whitney Houston.
“Hollywood” (from ‘American Life,’ 2003)
Madonna performing "Hollywood," a song from her "American Life" album reflecting on fame and superficiality of Hollywood culture.
While American Life (2003) marked a departure and a commercial dip after the successes of Ray of Light and Music, “Hollywood” remained a powerful and insightful track. Its acoustic guitar riff and steady beat underscored Madonna’s reflections on the allure and pitfalls of Hollywood. “Hollywood,” Madonna explained on the video set, “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.” The song serves as a commentary on fame, illusion, and the potential for self-loss in pursuit of the “American Dream.”
“Ghosttown” (from ‘Rebel Heart,’ 2015)
Madonna in "Ghosttown" music video, a song about resilience and human connection in a post-apocalyptic world, from her "Rebel Heart" album.
“Ghosttown,” a standout ballad from Rebel Heart, explores themes of enduring love and human connection amidst societal collapse. The song envisions a world stripped of modern conveniences, emphasizing the primal need for companionship. “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 elaborated. Co-written with Sean Douglas, whose work on Jason Derulo’s “Talk Dirty” impressed Madonna, the song was created in just three days, becoming a testament to spontaneous creativity and profound thematic resonance.
“Bad Girl” (from ‘Erotica,’ 1992)
Madonna in "Bad Girl" music video, a melancholic ballad from "Erotica" album exploring themes of guilt and self-destructive behavior.
“Bad Girl,” from the Erotica album, offers a somber and introspective look at self-destructive patterns and emotional dissatisfaction. Sung from the perspective of a woman trapped in a cycle of fleeting encounters, the lyrics convey a sense of guilt and unhappiness. “Drunk by six/ Kissing someone else’s lips,” Madonna sings, “I’m not happy when I act this way.” Producer Shep Pettibone noted Madonna’s rapid songwriting and recording process and her increasing depth of lyrical content during this period. “Madonna’s stories were getting a lot more serious and intense, driving the creative direction of the songs into deeply personal territory.”
“Everybody” (from ‘Madonna,’ 1983)
Madonna's debut single "Everybody," marking the beginning of her iconic music career in the early 80s.
“Everybody” marked Madonna’s entry into the music scene, a demo track that caught the ear of DJ Mark Kamins at New York’s Danceteria. Kamins’ enthusiastic reaction led to him playing the song, which in turn garnered attention and ultimately secured Madonna a contract with Sire Records. Sire president Seymour Stein, upon hearing “Everybody” while hospitalized, was immediately convinced of Madonna’s potential. “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.” The song’s raw energy and danceable rhythm became foundational to Madonna’s early sound.
“La Isla Bonita” (from ‘True Blue,’ 1986)
Madonna in "La Isla Bonita" music video, showcasing her Latin-inspired style and flamenco dancer persona.
“La Isla Bonita” was a stylistic departure for Madonna, embracing Latin influences with Spanish guitar, Cuban percussion, and lyrics evoking dreams of a beautiful island, San Pedro. Co-written with Patrick Leonard and Bruce Gaitsch, the song was originally intended for Michael Jackson, who rejected it due to the title. Madonna embraced the track, tailoring the lyrics to her vision of “the beauty and mystery of Latin American people.” Despite not knowing the real San Pedro, Madonna’s imagination brought the exotic locale to life in the song and its theatrical music video, which features her as a flamenco dancer, influencing artists like Lady Gaga.
“Bitch I’m Madonna” (from ‘Rebel Heart,’ 2015)
Madonna performing "Bitch I'm Madonna" with Nicki Minaj, an assertive track from "Rebel Heart" challenging ageism in the music industry.
“Bitch I’m Madonna,” from Rebel Heart, is an unapologetic and defiant anthem, directly addressing ageism and sexism prevalent in the music industry. Thirteen albums into her career, Madonna delivered a bold statement of enduring relevance. “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.” Produced by Diplo and featuring a rap verse by Nicki Minaj, the song is a high-energy track with shifting tempos, embodying Madonna’s continued artistic rebellion.
“Keep It Together” (from ‘Like a Prayer,’ 1989)
Madonna in "Keep It Together" music video, a song from "Like a Prayer" album celebrating family bonds and inspired by Sly & the Family Stone.
“Keep It Together,” from Like a Prayer, is an upbeat celebration of family bonds, influenced by Sly and the Family Stone’s “Family Affair” and Sister Sledge’s “We Are Family.” Amidst the album’s heavier themes, this track offers a message of familial solidarity. “Family is everything. Family comes first,” Madonna stated, emphasizing the song’s core message. She called “Keep It Together” a tribute to Sly Stone, reflecting on her upbringing and personal growth. “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.”
“Deeper and Deeper” (from ‘Erotica,’ 1992)
Madonna performing "Deeper and Deeper," a house-flavored track from "Erotica" album referencing her hit "Vogue".
“Deeper and Deeper,” from Erotica, is a house-infused track that playfully references Madonna’s iconic dance hit “Vogue.” Producer Shep Pettibone recalled the spontaneous creative process, leading to the inclusion of the “Vogue” lyric. “We got to that point, and we’re like, ‘What the hell. Let’s have fun with it,'” he said. Despite Pettibone’s initial reservations about incorporating a flamenco guitar solo, Madonna’s vision prevailed, resulting in a unique blend of house and Latin sounds, showcasing her willingness to experiment and push genre boundaries.
“Hanky Panky” (from ‘I’m Breathless,’ 1990)
Madonna in "Dick Tracy," the movie inspiring her jazzy and playful song "Hanky Panky" from "I'm Breathless" album.
“Hanky Panky,” from I’m Breathless, is a jazzy, tongue-in-cheek ode to spanking, inspired by Madonna’s character Breathless Mahoney in the film Dick Tracy. During her Blond Ambition Tour in 1990, Madonna playfully introduced the song, highlighting its playful and provocative nature. The lyrics, “Some girls, they like candy, and others, they like to grind,” encapsulate the song’s flirtatious and slightly risqué theme, delivered with Madonna’s characteristic wit and confidence.
“Lucky Star” (from ‘Madonna,’ 1983)
Madonna's early look in "Lucky Star" music video, a shimmering synth-pop song from her debut album "Madonna".
“Lucky Star,” the opening track of Madonna’s debut album, is a shimmering synth-pop gem that solidified her early sound and image. Originally written for DJ Mark Kamins, the song’s catchy melody and suggestive lyrics about a lover’s “heavenly body” made it an instant hit. After initial R&B-leaning demo, Jellybean Benitez refined the track with a funky guitar line, enhancing its dance-pop appeal. The song’s music video, frequently aired on MTV, cemented Madonna’s fashion influence, popularizing hair ribbons and cut-off gloves.
“4 Minutes” (from ‘Hard Candy,’ 2008)
Madonna and Justin Timberlake performing "4 Minutes," a high-energy collaboration from "Hard Candy" album.
“4 Minutes,” from Hard Candy, marked Madonna’s return to sexually charged pop, collaborating with R&B and hip-hop producers Timbaland, Pharrell Williams, and Justin Timberlake. The track, featuring Timberlake, is a high-energy, marching band-inspired song with a “tick-tock” refrain, symbolizing urgency and awareness. Madonna described the song as a paradox, “like we’re saying, ‘We’re running out of time – people, wake up,’ but ‘if we are going to save the world, can we please have a good time while we’re doing it?'” The collaboration with Timberlake was sparked by shared concerns for children in Malawi, blending social consciousness with danceable pop.
“True Blue” (from ‘True Blue,’ 1986)
Madonna in "True Blue" music video, a charming and romantic song from the "True Blue" album, named after Sean Penn's expression.
“True Blue,” the title track from the album of the same name, exudes a blissful and romantic sentiment, reflecting Madonna’s personal life at the time. Married to Sean Penn, she named the song and album after his favorite expression. The song’s girl-group influences, quaint rhythm, and charming video captured a moment of romantic happiness in Madonna’s life. Despite later divorcing Penn and ceasing to perform the song, she fondly recalled “True Blue” as representing “romance.”
“I Deserve It” (from ‘Music,’ 2000)
Madonna performing "I Deserve It," a unique blend of acoustic and electronic sounds from "Music" album.
“I Deserve It,” from Music, is described by Madonna as a “lonely love song,” blending earnest lyrics with acoustic guitar and dissonant synth elements. The track’s unusual combination of acoustic and electronic sounds creates a sense of unease, which Madonna found intriguing. “The juxtaposition of the acoustic guitar and then that synth siren sound, to me, that strange combination makes it a little bit uncomfortable,” she explained. Producer Mirwais intentionally left Madonna’s vocals unprocessed, highlighting their raw purity and emotional depth.
“Gambler” (from ‘Vision Quest,’ 1985)
Madonna in "Vision Quest," the movie featuring her energetic dance track "Gambler".
“Gambler,” recorded for the film Vision Quest, is an assertive and energetic dance track written by Madonna and produced by Jellybean Benitez around the time of her debut album. The song’s confident and independent spirit aligns with the film’s heroine. “‘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.” Despite not being released as a single, “Gambler” became a staple of her Virgin Tour, showcasing its enduring popularity with fans.
“Take a Bow” (from ‘Bedtime Stories,’ 1994)
Madonna in "Take a Bow" music video, a grand and theatrical ballad from "Bedtime Stories" album, quoting Shakespeare.
“Take a Bow,” concluding Bedtime Stories, is a dramatic ballad, quoting Shakespeare and signaling the end of a relationship. Co-written with Kenneth “Babyface” Edmonds, known for R&B hits, the song aimed for a lush and emotional sound. Edmonds focused on creating a grand ballad rather than chart-focused pop. “She came to me for lush ballads, so that’s where we went,” Edmonds recalled. “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.” The song’s theatricality and emotional depth made it a powerful album closer.
“Frozen” (from ‘Ray of Light,’ 1998 )
Madonna in "Frozen" music video, a cold and cinematic ballad from "Ray of Light" album inspired by "The Sheltering Sky" movie.
“Frozen,” from Ray of Light, is a cold, cinematic, electro-infused ballad expressing themes of “retaliation, revenge, hate [and] regret.” Inspired by The Sheltering Sky, the song explores love under pressure and incorporates Moroccan-influenced beats. Madonna’s demo version stretched to ten minutes, reflecting her deep immersion in the song’s creation. The music video, filmed in the Mojave Desert, aimed to visually embody “female angst,” enhancing the song’s intense emotional atmosphere.
“Cherish” (from ‘Like a Prayer,’ 1989)
Madonna in "Cherish" music video, an optimistic and upbeat love song from "Like a Prayer" album.
“Cherish,” from Like a Prayer, stands out as one of Madonna’s most optimistic love songs, inspired by Romeo and Juliet. Madonna described its creation as coming from a “superhyper-positive state of mind.” The song’s upbeat tempo and playful video, directed by Herb Ritts, contributed to its Number Two chart success. Madonna expressed surprise at the song’s popularity, noting, “The songs that I think are the most retarded songs I’ve written, like ‘Cherish’… end up being the biggest hits.”
“Don’t Tell Me” (from ‘Music,’ 2000)
Madonna performing "Don't Tell Me," a country-electro fusion song from "Music" album.
“Don’t Tell Me,” from Music, surprised listeners with its twangy, country-infused take on electro-pop. Originating as a tango written by her brother-in-law, Joe Henry, Madonna and producer Mirwais transformed it during sessions in London. Madonna was drawn to the song’s defiant sentiment, “‘Don’t tell me to stop.'” Joe Henry noted the transformation of his tango into Madonna’s groove-centric version, highlighting the song’s genre-bending evolution.
“Beautiful Stranger” (from ‘The Spy Who Shagged Me,’ 1999)
Madonna in "Austin Powers," the movie featuring her groovy song "Beautiful Stranger" on the soundtrack.
“Beautiful Stranger,” from The Spy Who Shagged Me soundtrack, blends electronica with Sixties psych-pop, a collaboration with producer William Orbit. The song’s creation had a backstory involving Mike Myers and a hypothetical remake of Some Like It Hot. While that film project didn’t materialize, Madonna contributed this hit track to the Austin Powers sequel. Introducing the video, Madonna simply described the song as “groovy, baby,” capturing its lighthearted and catchy nature.
“Where’s the Party” (from ‘True Blue,’ 1986)
Madonna performing "Where's the Party," an energetic and escapist track from "True Blue" album.
“Where’s the Party,” from True Blue, is an ode to weekend escapism, reminiscent of Madonna’s early tracks like “Everybody” and “Holiday.” While seemingly lighter in tone compared to other True Blue songs, it held personal significance for Madonna. It served as a response to negative press coverage. Speaking to The New York Times, she described it as “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.” The song embodies a desire for joy and resilience against external pressures.
“Physical Attraction” (from ‘Madonna,’ 1983)
Madonna's early days, featuring "Physical Attraction" from her debut album, a flirty track hinting at her provocative persona.
“Physical Attraction,” from Madonna’s debut album, is a flirty and suggestive early track that hinted at her future provocative image. The B-side to “Burning Up,” it showcased Madonna’s dance-oriented sound and growing appeal. Sire Records executive Michael Rosenblatt highlighted Reggie Lucas’ contribution, noting he wrote “Borderline” and “Physical Attraction.” Lucas emphasized the creative freedom of those early sessions, stating, “There was no committee rendering judgment from on high, because she was brand new and frankly nobody cared about her that much.”
“Who’s That Girl” (from ‘Who’s That Girl,’ 1987)
Madonna in "Who's That Girl" movie, the film and soundtrack featuring her hit song of the same name.
“Who’s That Girl,” the title track from her third movie soundtrack, was a quickly conceived hit. Co-writer Patrick Leonard recalled Madonna arriving with the chorus idea. “I had this chorus,” Leonard said. “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 on her “feisty femme” character Nikki Finn, the song is upbeat dance-pop, outperforming the film it accompanied.
“Holiday” (from ‘Madonna,’ 1983)
Madonna in "Holiday" music video, her breakthrough hit from debut album "Madonna", an anthem of escapism and joy.
“Holiday,” from Madonna, became Madonna’s first Top 20 single and a career-defining track. Sire Records A&R rep Michael Rosenblatt sought an uptempo pop song to complete her debut album. Jellybean Benitez delivered “Holiday,” written by Curtis Hudson and Lisa Stevens of Pure Energy and revamped by Benitez and Madonna. Initially released as a B-side, its infectious energy and message of escapism resonated widely. Benitez recognized its immediate appeal to DJs, stating, “I knew that as soon as DJs saw John ‘Jellybean’ Benitez on the ‘Holiday’ side, that was it, because DJs stick together.”
“Human Nature” (from ‘Bedtime Stories,’ 1994)
Madonna in "Human Nature" music video, a defiant response to media criticism from "Bedtime Stories" album.
“Human Nature,” from Bedtime Stories, is a direct and defiant response to media backlash following her Erotica era. Madonna described it as saying, “‘Don’t put me in a box, don’t pin me down, don’t tell me what I can and can’t say. It’s about breaking out of restraints.'” The lyrics directly address the controversy surrounding her Erotica album and Sex book. Musically, it incorporates hip-hop and R&B elements, sampling Main Source and referencing A Tribe Called Quest, reflecting Madonna’s genre fluidity.
“Drowned World/ Substitute for Love” (from ‘Ray of Light,’ 1998)
Madonna with daughter Lourdes, inspiring "Drowned World/Substitute for Love" from "Ray of Light" album, reflecting on motherhood and fame.
“Drowned World/ Substitute for Love,” the opening track of Ray of Light, reflects on motherhood and evolving perspectives on fame. Between albums, Madonna gave birth to her daughter Lourdes, a life-changing event that deeply influenced Ray of Light. “I got pregnant, and the whole idea of giving birth and being responsible for another life put me in a different place,” she explained. The song explores personal epiphanies, shifting focus from external reinvention to internal revelation.
“What It Feels Like for a Girl” (from ‘Music’, 2000)
Madonna in "What It Feels Like for a Girl" music video, a controversial track from "Music" album exploring gender stereotypes.
“What It Feels Like for a Girl,” from Music, features a controversial video directed by Guy Ritchie, banned by MTV. The song opens with a Charlotte Gainsbourg monologue on gender roles, setting the stage for Madonna’s exploration of female empowerment and societal expectations. “Our generation has been encouraged to grab life by the balls, be superindependent,” Madonna said, “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.” The track challenges gender stereotypes and celebrates female strength.
“Angel” (from ‘Like a Virgin,’ 1984)
Madonna in "Angel" era, a song from "Like a Virgin" album exploring themes of heavenly love and spiritual connection.
“Angel,” from Like a Virgin, delves into spiritual themes, reflecting Madonna’s Catholic upbringing. “I think it’s important to call angels to you to protect you,” Madonna stated. The song is an ode to a heavenly love, “full of wonder and surprise,” with Madonna’s giggling intro adding a playful touch. Co-written with Stephen Bray, “Angel” became a hit without a dedicated music video due to the heavy rotation of her other videos at the time.
“Justify My Love” (from ‘The Immaculate Collection,’ 1990)
Madonna in "Justify My Love" music video, an understated and sensual hit from "The Immaculate Collection" album.
“Justify My Love,” from The Immaculate Collection, is an understated yet sensual hit with a spare groove built around a Public Enemy sample. Written by Lenny Kravitz and Ingrid Chavez, the lyrics originated from an unmailed love letter Chavez wrote to Kravitz. MTV banned its erotic video, prompting Madonna to defend her artistic intentions on Nightline. “We’re dealing with sexual fantasies,” she explained. “And being truthful and honest with our partner, and these feelings exist. I’m just dealing with the truth here.” The song and video challenged censorship and explored themes of sexuality and truth.
“Open Your Heart” (from ‘True Blue,’ 1986)
Madonna in "Open Your Heart" music video, a quintessential 80s dance-pop hit from "True Blue" album.
“Open Your Heart,” from True Blue, was originally a rock song intended for Cyndi Lauper or The Temptations. Songwriters Gardner Cole and Peter Rafelson created “Follow Your Heart,” which Madonna and Patrick Leonard transformed into a quintessential 80s dance-pop anthem. They flipped the arrangement, added a bass line, and created a clipped-beat jam. Paired with a peep-show-themed video, “Open Your Heart” became Madonna’s third Number One single from True Blue, showcasing her ability to reinvent and popularize songs.
“Dress You Up” (from ‘Like a Virgin,’ 1984)
Madonna performing "Dress You Up" on Virgin Tour, a snappy and funky hit from "Like a Virgin" album.
“Dress You Up,” from Like a Virgin, is a snappy and playful love pledge with production by Nile Rodgers. Despite its PG-rated lyrics, it was controversially flagged by the Parents Music Resource Center as part of the “Filthy Fifteen.” The song became a style anthem, particularly evident in its live video from The Virgin Tour, showing fans emulating Madonna’s fashion. Rodgers described Madonna’s impact: “In a low-res world, she was high-definition hyperrealism,” highlighting her revolutionary presence in pop culture.
“Promise to Try” (from ‘Like a Prayer,’ 1989)
Madonna in "Truth or Dare," featuring "Promise to Try" a tearjerker ballad from "Like a Prayer" album about her mother.
“Promise to Try,” from Like a Prayer, is a deeply emotional piano ballad about Madonna’s mother, who died when Madonna was five. Co-written with Patrick Leonard, the song is a poignant tearjerker. “Little girl don’t you forget her face/Laughing away your tears/When she was the one who felt all the pain,” Madonna sings, channeling multiple perspectives. She described it as “my father talking to me, and it’s me talking to me.” The song is featured in Truth or Dare during Madonna’s visit to her mother’s grave, underscoring its personal and vulnerable nature.
“Material Girl” (from ‘Like a Virgin,’ 1984)
Madonna in "Material Girl" music video, an iconic song from "Like a Virgin" album ironically defining her "Material Girl" persona.
“Material Girl,” from Like a Virgin, ironically became Madonna’s defining moniker, despite her not identifying with its materialistic message. While she didn’t write the song and later expressed it didn’t represent her values, she appreciated its “gawky swagger.” Nile Rodgers’ New Wave production amplified its appeal, making it a major hit. Rodgers initially thought “Material Girl,” not “Like a Virgin,” would be the bigger hit, and indeed, the “Material Girl” label stuck with Madonna, becoming a lasting part of her image.
“Express Yourself” (from ‘Like a Prayer,’ 1989)
Madonna in "Express Yourself" music video, a girl-power anthem from "Like a Prayer" album inspired by Staple Singers.
“Express Yourself,” from Like a Prayer, is a powerful girl-power anthem, drawing inspiration from the Staple Singers’ “Respect Yourself.” Madonna encourages female assertiveness, singing, “If you don’t say what you want, then you’re not going to get it.” The song reached Number Two and its David Fincher-directed video was the most expensive ever made at the time. Its iconic status is such that Lady Gaga’s “Born This Way” drew direct comparisons. Madonna herself quipped, “When I heard [it] on the radio… I said, ‘That sounds very familiar,'” acknowledging its lasting impact and influence.
“Crazy for You” (from ‘Vision Quest’, 1985)
Madonna performing "Crazy for You" in "Vision Quest," a breakthrough ballad showcasing her vocal versatility.
“Crazy for You,” from Vision Quest, was Madonna’s second Number One single, a ballad produced by Jellybean Benitez. Initially, songwriter John Bettis questioned Madonna’s ability to sing such a song. The single became the highlight of Vision Quest, soundtracking a romance and mirroring Madonna’s own mainstream breakthrough. The movie features Madonna performing the song in her first screen appearance, linking her image to mainstream appeal.
“Burning Up” (from ‘Madonna’, 1983)
Madonna's early rebellious look in "Burning Up" music video, an electro-rock club banger from her debut album "Madonna".
“Burning Up,” from Madonna, is an early club banger that showcased Madonna’s raw energy and edgy style. Initially a demo, it was re-recorded with Reggie Lucas and remixed by Jellybean Benitez, resulting in an electro-jam with rock guitar elements. The song’s steamy video and Madonna’s rebellious image helped it climb the dance charts. Jellybean Benitez recognized her potential early on, though even he underestimated her ultimate level of success. “I knew she was gonna be big,” Benitez said. “That her album could go gold. I never thought it could go six-times platinum.”
“Music” (from ‘Music’, 2000)
Madonna in "Music" music video with Sacha Baron Cohen, a democratizing anthem celebrating the power of music.
“Music,” the title track from Music, explicitly celebrates the unifying power of music. Ironically, inspiration came from a Sting concert, where fans only became truly engaged during Police hits. “Everyone was practically holding hands… I mean, it really moved me,” Madonna told Rolling Stone. “And I thought, ‘That’s what music does to people.'” Produced by Mirwais, the glitchy disco track became a Number One hit. Its video, featuring Sacha Baron Cohen, visually represented music’s ability to unite diverse groups, even as Madonna was pregnant, emphasizing themes of unity and universal appeal.
“Ray of Light” (from ‘Ray of Light,’ 1998)
Madonna in "Ray of Light" music video, a futuristic electronica track from "Ray of Light" album, showcasing vocal power and spiritual themes.
“Ray of Light,” the title track from Ray of Light, is a futuristic electronica song that marked a significant sonic evolution for Madonna. Producer William Orbit sent Madonna a DAT with tracks, including an interpolation of “Sepheryn.” Madonna adapted the lyrics to convey “wonderment” and spiritual awakening. “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.” The song’s complex production and Madonna’s powerful vocals, honed during Evita vocal training, showcased her artistic growth. Orbit emphasized Madonna’s integral role in the album’s production, highlighting her often-overlooked creative input.
“Live to Tell” (from ‘True Blue,’ 1986)
Madonna in "Live to Tell" music video, a moody and confessional ballad from "True Blue" album, exploring hidden secrets.
“Live to Tell,” from True Blue, introduced a new, introspective side of Madonna with its moody, confessional ballad style. Its unconventional structure and lyrics about hidden secrets marked a departure from her earlier work. Madonna wrote the lyrics quickly to Patrick Leonard’s track and recorded the vocal in a single take. Initially considered commercially risky, it became her third Number One hit, validating her artistic risks. The song’s ambiguous lyrics invited varied interpretations, with Madonna intentionally keeping its true meaning veiled, adding to its mystique and emotional resonance.
“Hung Up” (from ‘Confessions on a Dance Floor,’ 2005)
Madonna performing "Hung Up," a high-energy disco track from "Confessions on a Dance Floor" album, sampling ABBA.
“Hung Up,” from Confessions on a Dance Floor, is a high-energy disco revival track that reaffirmed Madonna’s dance-floor dominance decades into her career. Returning to her “aerobics record” roots, “Hung Up” was recorded in producer Stuart Price’s London apartment, echoing the stripped-down energy of her early records. The song famously samples ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight),” adding a layer of Eurodisco nostalgia. Madonna’s looped vocals and sped-up clock sound effects enhance the track’s frenetic energy, creating a dance-floor time warp that remains one of her most seductive and surprising hits.
“Like a Virgin” (from ‘Like a Virgin,’ 1984)
Madonna in "Like a Virgin" music video, an iconic song from "Like a Virgin" album defining her provocative image and MTV breakthrough.
“Like a Virgin,” the title track from Like a Virgin, became a defining song for Madonna, saturated with implied sensuality despite minimal overt sexual references in the lyrics. Written by Billy Steinberg and Tom Kelly, Madonna embraced the song despite suggestions to change its title. Her iconic performance at the 1984 MTV VMAs, in a wedding dress, humping the stage, cemented the song’s and her image’s indelibility. Madonna expressed surprise at the reaction, stating she intended to convey feelings of freshness and newness, while public interpretation leaned towards more explicit sexual themes, highlighting the power of her performance and persona to shape meaning.
“Borderline” (from ‘Madonna,’ 1983)
Madonna in "Borderline" music video, her breakthrough hit from debut album "Madonna", blending pop and R&B styles.
“Borderline,” from Madonna, was Madonna’s breakthrough hit, propelling her from urban radio to mainstream pop stardom. Produced by Reggie Lucas, the song blended pop and R&B elements, creating a unique downtown cool vibe. Lucas, unfazed by Madonna’s bohemian style due to his diverse musical background, helped craft a track that resonated widely. “Borderline” became Madonna’s first Top 10 hit, and its music video, featuring an interracial love story, further defined her early style for MTV audiences. Madonna revisited the song in a punk rock style on her 2008 tour, demonstrating its enduring versatility.
“Vogue” (from ‘I’m Breathless,’ 1990)
Madonna in "Vogue" music video, her iconic house track from "I'm Breathless" album, celebrating dance and LGBTQ+ culture.
“Vogue,” from I’m Breathless, is Madonna’s most audacious manifesto, celebrating dance, fashion, and LGBTQ+ culture. The 1990 smash hit pays tribute to old Hollywood glamour and New York’s gay ball culture, later popularized by Paris Is Burning. Madonna frequented Sound Factory, observing voguing dancers, inspiring the song. Co-producer Shep Pettibone was a DJ at Sound Factory, further grounding the song in authentic ball culture. Madonna used “Vogue” for a Rock the Vote ad, changing lyrics to include social justice icons, underscoring its political and cultural significance during the Reagan-Bush era.
“Into the Groove” (Non-album single, 1985)
Madonna in "Desperately Seeking Susan," the movie featuring her iconic dance track "Into the Groove".
“Into the Groove,” a non-album single, is a streetwise dance anthem born from Madonna’s early struggles in New York. Reflecting on her time squatting and facing hardship, she and Stephen Bray created an eight-track demo. Bray focused on the music’s “skeleton,” while Madonna added lyrics and the song’s bridge. Featured in Desperately Seeking Susan, the song unexpectedly became a radio hit, retaining its raw, demo-like quality. Its raw energy and Madonna’s urgent vocals made it a definitive dance track, ruling radio and dance floors ever since.
“Like a Prayer” (from ‘Like a Prayer,’ 1989)
Madonna in "Like a Prayer" music video, her greatest song from "Like a Prayer" album, blending gospel, disco, and controversial religious imagery.
“Like a Prayer,” the title track from Like a Prayer, is widely considered Madonna’s greatest song, embodying her long-standing fascination with the intersection of sex and spirituality. The 1989 gospel-disco smash blends religious and sensual themes, evident in lyrics like, “I’m down on my knees/I wanna take you there,” open to interpretations of prayer and intimacy. Madonna herself stated, “I pray when I’m in trouble or when I’m happy. When I feel any kind of extreme.” The song’s controversial music video, featuring religious iconography, burning crosses, and sensual scenes, sparked immediate outrage and condemnation, overshadowing a Pepsi ad campaign it initially launched. Yet, the controversy amplified the song’s impact, solidifying “Like a Prayer” as a masterpiece that encapsulates Madonna’s musical and emotional extremes.
Madonna’s enduring legacy is cemented by these 50 songs, each a chapter in her ever-evolving story. From early dance anthems to introspective ballads and genre-bending experiments, her music continues to resonate, challenge, and inspire. “Madonna Singer Songs” remain a vital part of the pop culture landscape, a testament to her unparalleled artistry and impact.
