40 years of Madonna: The Queen of Pop's greatest songs, ranked

The softest and sweetest moment on the highly charged Erotica, “Rain” is a gorgeous, subtle ballad, pitched halfway between an R&B slow jam and shimmering new age healing. That the song could be interpreted either as a seduction or a cleansing affirmation speaks to the subtle tension between its rhythm and execution: the subdued pulse suggests something seductive, yet the washes of keyboards and vocal harmonies are comforting and consoling, a duality that gives “Rain” depth and complexity.

The cornerstone not only of the Erotica album but also its accompanying Sex book, “Erotica” introduces Madonna’s short-lived alter-ego Dita, who acts as a ringleader for sexual experiences that fall just short of decadence. Working with co-producer Shep Pettibone, Madonna grounds “Erotica” in the house-inflected dance of the early 1990s, finding sultriness within its bustling dance loops and clean-angled synth stabs. “Erotica” isn’t shy about its carnality yet it feels slightly and alluringly elusive: it’s a tease, with all the truly sexy moments happening just outside of view.

As the opening cut on Madonna’s middle-aged masterpiece Ray Of Light, “Drowned World/Substitute For Love” serves as a musical and thematic keynote for the rest of the record, establishing her immersion into ambient electronica and newfound spiritual searching. Unfolding slowly, “Drowned World/Substitute For Love” finds Madonna in an explicitly autobiographical mode, framing her life choices as “I traded fame for love without a second thought.” Over the course of five minutes, she explores the ramifications of this, concluding that she’s changed her mind and found religion, a conversion telegraphed by William Orbit’s steadily intensifying production, where additional samples, rhythms, and instrumental flourishes all reinforce Madonna’s naked honesty.

A continuation of “Vogue”—there’s a nod to the earlier hit in the single’s closing moments—”Deeper And Deeper” is a ray of a light within the darkly provocative Erotica, a pure celebration of the power of dance. The swirl of synthesized strings and bold, glassy keyboards are simultaneously modern ’90s house and a callback to the glory days of the glitter ball, a combination that only grows in intensity as the song builds to the unexpected release of a flamenco guitar solo on the bridge.

The theme song to Madonna’s second major movie, “Who’s That Girl” picks up the thread left hanging by “La Isla Bonita.” Where that hit—also released in 1987—pushed conventional Latin music tropes to the forefront, Madonna and Patrick Leonard integrate Latin rhythms within the context of a bright, lively dance-pop number, adding a Spanish-sung countermelody to the song’s chorus. If this lacks the freshness of “La Isla Bonita,” there’s a slightly haunted quality to the delivery of the titular phrase that lets “Who’s That Girl” linger after it’s done playing.

A kindred spirit to “True Blue,” “Cherish” echoes the breezy innocence of 1960s girl groups, its nostalgic bent tempered by the rhythm track’s synthesized bop. There isn’t a trace of cynicism or irony to “Cherish,” which makes it stand out not only on its parent album Like A Prayer but in Madonna’s catalog in general: it’s a sweet confection, an incandescent ray of sunshine that illuminates everything it touches.

A rare collaboration between Madonna and her two chief 1980s co-writers, Stephen Bray and Patrick Leonard, “Where’s The Party” is a cousin to “Into The Groove,” a song where the narrator is seeking escape within the sound of music. Teeming with over-active synthesizers and excitable drum machines, “Where’s The Party” is almost too lively to be a dance song. Rather, it creates excitement through its chaotic high spirits with Madonna serving as a ringleader for a party that lasts all night long.

After the divisive American Life, Madonna designed 2005’s Confessions On A Dance Floor as an audacious celebration of dance music, both past and present. “Hung Up,” the record’s first single, was caught between these two extremes, with the nagging sample from ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight)“ conjuring the ghost of disco past, but this specter is seen through a distorted funhouse mirror. “Hung Up” discards nostalgia for trippy, elastic modernity that serves as a reminder of how often Madonna managed unexpected reinventions of her music and herself.

The start of Madonna’s long collaboration with songwriter/producer Patrick Leonard, the stately ballad “Live To Tell” was released as part of the soundtrack to At Close Range, a crime drama featuring the singer’s then-romantic partner Sean Penn. “Live To Tell” marked a conscious maturation for Madonna. The ballad contains no overt romance: it’s about living with loss, learning how to bear the scars of a deep wound. Fittingly, the arrangement is spartan, allowing Madonna to take center stage with a vocal performance that remains among her most affecting recordings.

Madonna may have written “Lucky Star” with hopes that it would get played at the New York club Danceteria, but it feels as if it was destined to be her first pop smash hit, which is precisely what it turned out to be. John “Jellybean” Benitez mixed the original Reggie Lucas production, giving the song an urgency, decorating the synthesized disco beat with soulful flourishes and New Wave accouterments. It’s a sound that’s designed for dance floors, yet it’s ultimately eclipsed by Madonna’s melody, which is powered by an incandescent hook that’s pure pop.

When Madonna took the assignment to contribute a song to Austin Powers: The Spy Who Shagged Me, she cleverly designed “Beautiful Stranger” to appeal to both to the swinging ’60s fantasia constructed by Mike Myers and also her own electronica rebirth. Re-teaming with producer William Orbit, Madonna deliberately eschews the spiritual heavy lifting of Ray Of Light while retaining its vibrant blend of futuristic dance and retro-psychedelia. The combination is exquisite: with another production, “Beautiful Stranger” could’ve been a hit in 1969, but the combination of modern rhythms and retro affectations made it an ideal pop single for 1999.

A collaboration with Patrick Leonard—he brought the original demo track to Michael Jackson, who rejected it—“La Isla Bonita” is Madonna’s first explicit foray into Latin music. In some respects, it reveals how Madonna was just beginning to amass knowledge of Latin culture—she would later reveal that she did not know where the San Pedro of the lyric actually resides—but there’s a breezy charm to the single’s blend of Cuban and Spanish instrumentation, one that creates a fantasy of an extended tropical vacation.

Just four months after Like A Virgin dropped, Madonna delivered her purest ballad to date: the slow-burning “Crazy For You.” The song was recorded for Vision Quest, a wrestling melodrama starring Matthew Modine and Linda Fiorentino that featured Madonna as a singer in a bar. The ballad was new territory for both Madonna and her producer, John “Jellybean” Benitez, and the pair rose to the occasion. Madonna’s performance is passionate and earnest, while Jellybean avoids power ballad cliches, letting the song simmer by grounding it with an elastic synth-bass and decorating it with evocative synths that give the song a subdued cinematic quality.

Like “Live To Tell” before it, “Papa Don’t Preach” is consciously mature, a move away from standard pop and dance fare from Madonna. Unlike its predecessor, “Papa Don’t Preach” isn’t a ballad: it’s firmly within Madonna’s dance-pop wheelhouse, an opulent ’80s single driven by electronic rhythms and outfitted with synth flourishes. Underneath those recognizable sounds, Madonna tells the tale of an unexpectedly pregnant teenager who asks her father for support. Cleverly clothing her ultimately pro-life sentiment within the guise of a self-empowering chorus, Madonna attempts to have it both ways with “Papa Don’t Preach”—the fate of the pregnancy is clearly the teenager’s decision yet she resolves not to have an abortion—a choice that lends the song some humanity: it doesn’t play like an adult trying to appease both sides of her audience but the confusion of an adolescent caught in unwanted circumstances.

All these years later, Madonna’s debut single sounds simultaneously tentative and vibrant. So many of the musical seeds that would later blossom are here, particularly how Madonna does not neglect to give her song a bright, insistent pop hook even when she places an emphasis on a fresh, vital dance beat. With its percolating synthesizers and snapping drum machine, “Everybody” does seem like a relic of the early 1980s, yet it hasn’t lost its potency, probably because Madonna constructed it as a rallying cry to unite listeners of all stripes on the utopia of the dance floor.

Madonna collaborated with French producer Mirwais on a good chunk of Music, the album that found the singer heading further down the electronica avenues she opened up with Ray Of Light. Mirwais conjures a bit of electro-funk reminiscent of Daft Punk, the sinewy, robotic beat allowing Madonna to celebrate the deliverance of dancing. Madonna delivers a single that lives up to her boast that “music mix the bourgeoisie and the rebel”: “Music” exists simultaneously on the cutting edge of the dance club and is as undeniably hooky and intoxicating as her biggest radio hits.

“Frozen” served as an effective palate cleanser when it was released as the first single from Ray Of Light in 1998. Madonna spent the middle of the 1990s courting the middle of the road—she turned toward ballads, she starred as Evita in a silver screen spectacle—so the chilly electronica of “Frozen” offered a bracing reminder of her desire to remain on the vanguard of pop music. Working with producer/DJ William Orbit, Madonna drew upon downtempo electronica, establishing a vaguely foreboding atmosphere that’s brightened only slightly by flourishes of string suggesting arid desert vistas. Madonna pitches her vocal performance somewhere between cold and heat, breathing warmth into Orbit’s soundscapes but sounding wounded, even haunted, as she sings in a lower register that sounds as startling as her first foray into electronica.

The last of the singles pulled from Madonna’s eponymous debut, “Borderline” capitalized on the pop breakthrough of “Lucky Star.” Containing a stronger R&B bent than its predecessor—the song was written by Reggie Lucas, the producer who helmed a good chunk of Madonna—“Borderline” is propelled by a percolating synth-bass that’s punctuated by sweet keyboard stabs so colorful they read as New Wave, particularly when paired with Madonna’s earnest vocal. This fusion of sounds and sensibilities points toward the heights she’d soon reach on Like A Virgin.

Included as a new track on the epoch-defining compilation The Immaculate Collection, “Justify My Love” opened up a new era for Madonna. Working with a backing track conceived by Lenny Kravitz, Madonna doesn’t so much sing “Justify My Love” as intone its litany of erotic fantasies, her breathy delivery lending a sense of intimacy that helps balance the arty, off-kilter production. Far from being a one-off, “Justify My Love” turned out to be the gateway to the carnally charged Erotica era.

Arriving after “Everybody”’s cheerful call to arms, “Burning Up” feels intense and torrid. Madonna shifts her focus away from the collective energy of the dance floor, zeroing in on an interior obsession—namely, seduction. The slam of the drum beat intertwines with a prowling synth bass line, providing a sleek vehicle for Madonna’s sexually charged pleas. By design, it’s a single for dance clubs—the rhythms are nocturnal, the lyrics rife with carnality—and that gives “Burning Up” a dark freedom that “Lucky Star” and “Holiday” lack: it’s a song fueled by intense primal urges.

Where so much of Ray Of Light occupies distinctly introspective territory, its title track is a cathartic celebration of renewal. Here, Madonna positions her newly awakened spirituality as something of a rebirth—the chorus is built around the exclamation “And I feel like I just got home,” suggestions she’s rediscovered something essential about herself—a sensation she and William Orbit convey through a galloping beat accompanied by psychedelic fashions. It’s as infectious as it is incandescent, its joy emanating from the music and lyric equally.

Accompanied by a cheekily provocative clip where Madonna plays a stripper who befriended a young boy, “Open Your Heart” fittingly belongs among the singer’s most exuberant pop singles. Working with Patrick Leonard, Madonna turned a demo originally intended for Cyndi Lauper—the “Girls Just Want To Have Fun” singer never heard the recording—into bright, bustling dance-pop, a single filled with ornate baubles that’s underpinned by Madonna’s passionate performance. Her commitment helps downplay the song’s occasional innuendo, grounding this piece of buoyant pop in the realm of real, heartfelt emotions.

“Material Girl” cemented the superstardom that “Like A Virgin” gave Madonna, lending her a nickname that she didn’t necessarily deserve. For one thing, the glorification of riches and luxury goods in “Material Girl” hardly came from an autobiographical place. Madonna didn’t even write the song: it’s a Peter Brown and Robert Rans composition that the singer and producer Nile Rodgers brought to life, turning it into a piece of slick new wave disco so potent that it reshaped the face of pop music in the mid-1980s. There’s no denying that “Material Girl” belongs to the 1980s, a simultaneous celebration and critique of the Reagan years where the form ultimately overshadows the content … and that’s part of the message, too, that the meaning doesn’t matter as much as the execution, and few dance-pop singles are as flawless as “Material Girl.”

Part of Like A Prayer’s campaign of deliberate maturation, “Express Yourself” finds the singer who once claimed she was a “Material Girl” discovering the intoxication power of self-affirmation. As she rejects all the conventional trappings of a love affair—“Satin sheets are very romantic/What happens when you’re not in bed?”—Madonna keeps returning the focus to self-love and mutual respect, manifestos delivered to a thrilling rush of dance-funk inspired by Sly & the Family Stone but sounding as steely and imposing as a skyscraper.

Perhaps the most exquisite ballad Madonna ever recorded, “Take A Bow” chronicles the very end of a love affair, the moment where one person realizes their partner isn’t invested in the romance. There isn’t sadness here so much as resignation: the song is a silken sigh that’s almost sultry in its softness. Madonna enlisted Babyface, an auteur of seductive slow jams, as her collaborator for “Take A Bow” and while his touch is evident—his background vocals are clear in the mix—Madonna quietly commands attention, as she looks back at the failed relationship not with anger but affection.

The first of Madonna’s singles not to be written by the singer herself, “Holiday” also marks the beginning of her collaboration with John “Jellybean” Benitez, one of the great dance producers of the 1980s. Jellybean remixed several singles from Madonna’s self-titled debut but he produced “Holiday” on his own, giving the Curtis Hudson/Lisa Stevens-Crowder song a sparkling buoyancy that played as pop, a quality “Everybody” and “Burning Up” lacked. That infectious sense of joy—a savvy cross between underground disco and stylized New Wave—helped “Holiday” become Madonna’s international breakthrough single: it was her first song to reach the Billboard Top 40 and went all the way to No. 2 in the U.K.

Fueled by a spiritual longing and delivered as a provocation, “Like A Prayer” announced itself as a major work in 1989, a deliberate move into weighty thematic and musical material from an artist who was often pegged as frivolous. It almost feels like Madonna wanted to break that perception by throwing the kitchen sink at those preconceptions. “Like A Prayer” opens with a snippet of rock guitar, reveals itself as a secular gospel, then rides a sinewy dance rhythm to its conclusion. From its lyric to its arrangement, it’s overstuffed with ideas, its density giving it gravity but also endurance; it’s a mystery that begs to be explored.

Taking a song her singer/songwriter brother-in-law Joe Henry believed to be a “complete throwaway,” Madonna transformed “Stop” into “Don’t Tell Me,” a bold blend of folk-rock and electronica. Producer Mirwais turns the simple repeated acoustic guitar refrain into a stuttering mantra that underpins the self-empowerment of Madonna’s lyrics. The hall of mirrors aspect of Mirwais’ production turns a simple Americana tune into a stirring anthem that speaks to Madonna’s originality as an artist.

Lying at the center of Madonna’s legend, “Like A Virgin” turned the singer into a superstar upon its release in 1984, an ascendency due in part to the suggestive conceit at the heart of the song: it’s not about virginity but renewal, yet it’s hard to deny the inherent tease in the title. Madonna’s playful provocations highlight both her sexiness and wit, qualities that producer Nile Rodgers spotlights by pushing her youthful vocals at the forefront, placing his chicken-scratch guitar and insistent synth-bass in prime supporting roles. “Like A Virgin” is filled with colorful asides, such as Madonna’s inspired “Hey!” on the chorus and her murmured pleas on the fade-out, which make the record seem alive even after decades of over-exposure.

As “Into the Groove’’ ascends towards its chorus, Madonna sings “Only when I’m dancing can I feel this free,” a lyric that can be seen as a manifesto of sorts. Throughout her career, the dance floor has been her deliverance, a secular sacred place that provides refuge from any trouble. “Into The Groove’’ pays tribute to that hallowed venue by providing an enduring anthem to the pleasures of moving your body to the music, whether it’s in a club or in a bedroom where no one else can see.

Released at the apex of her power and popularity, “Vogue” crystalizes many of Madonna’s unique gifts. Returning to a familiar theme of finding self-discovery on the dance floor, Madonna is uncharacteristically specific on “Vogue,” ushering house music into the American mainstream and taking the underground dance sensation of vogueing along for the ride. Instead of succumbing to the temptations of appropriation, Madonna and co-writer/producer Shep Pettibone act as ambassadors for this subculture, presenting its daring, cutting-edge innovations in a stylish package that pays tribute to the source while also belonging unmistakably to Madonna. Not only would no other musician of her time be able to pull off this trick, they couldn’t imagine that it was possible.