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All 82 Madonna Singles Ranked

From “Everybody” to “I Don’t Search I Find,” we’ve ranked all 82 of the Queen of Pop’s singles.

Every Madonna Single Ranked
Editor’s Note: An earlier version of this list was originally published on August 1, 2018.

Madonna remains Billboard’s top Hot 100 solo artist of all time, second only to the Beatles. She holds the title for the female artist with the most Top 10 singles in the United States, and reigns as the female with the most #1 singles in the U.K. According to Mediabase, the music industry service that monitors radio airplay in the U.S., there are currently a dozen Madonna songs in regular rotation on adult-contemporary and classic radio stations across the country. By every objective measure, she’s the most successful singles artist of all time.

But Madonna cast aside her reputation as a “singles artist” relatively early in her career, with albums like Like a Prayer, Erotica, and Ray of Light making a case for the singer as a consummate artist. (Listen to our list of Madonna’s greatest album cuts and B-sides here.) Her colossal success on the pop charts, which generally rewards familiarity and predictability, was possible not because she bucked the system—though from “Live to Tell” to “Justify My Love” to “American Life,” she’s rarely played it safe—but because she struck a balance between embracing trends and setting them.

Earlier this year Madonna hit another milestone, when “I Don’t Search I Find” became her 50th #1 hit on Billboard’s club play chart—extending her record as the artist with the most #1’s on any Billboard chart in history. In honor of this achievement, we’ve updated our ranking of the Queen of Pop’s singles to include four songs from her latest album, Madame X. (Though she released several music videos to promote the album, our criteria for eligibility includes songs that were serviced to radio or clubs.)

The bottom of our list is, not surprisingly, populated largely by Madonna’s most recent singles. But the decline in the quality of her latter-day output is a mere footnote in a nearly four-decade career that has spanned—and, for the most part, mastered—pop, R&B, dance, electronica, and beyond, while simultaneously tackling taboo topics, elevating underground trends, empowering minorities, and pushing the boundaries of so-called good taste. Let’s get to it. Sal Cinquemani

82. “Revolver”

From the new songs on 1990’s The Immaculate Collection to…whatever the hell this is. Forget the uncharacteristic desperate crassness of choosing the then-hot Lil Wayne as a collaborator—much less deciding that he, of all people, is who you want adorning 2009’s Celebration, your most comprehensive greatest-hits package yet, one which still managed to find no room for “Deeper and Deeper” or “I’ll Remember.” Also, ignore the half-heartedness of the track’s electroclash gestures. What you have left is a clumsy sex-equals-guns metaphor that, with each passing year in America, grows more and more tone deaf. Eric Henderson

81. “Another Suitcase in Another Hall”

That Evita turned ostensibly liberal musical nerds into authoritarian apologists by emphasizing only the most superficial aspects of Peronism would be sinful enough, but in typical Andrew Lloyd Webber fashion, its songs are musically rote and lyrically bludgeoning. So goes “Another Suitcase in Another Hall,” a sleepy travelogue set to schmaltzy acoustic guitar and saxophone and a male chorus echoing Eva Perón’s—and by extension Madonna’s—self-pitying complaints about moving from one place to another. Political and psychological nuance, meanwhile, are nowhere in sight. Paul Schrodt

80. “Bitch I’m Madonna”

Yes. Yes, you are. And you fucking ought to know better. Henderson

79. “Girl Gone Wild”

The poison running through 2012’s “Girl Gone Wild” isn’t really its evidently deliberate disposability. Madonna could’ve covertly made a mockery of Benny Benassi’s crude David Guetta sheen if she’d been on her game. But the crassness of her performance reads sadly oblivious, and the demands to have fun are left sounding desperate. Like a Tumblr-meme version of “Get Together,” “Girl Gone Wild” is a rabbit hole of repurposed content (right down to the somewhat sacrilegious “Act of Contrition” swipe), ready for you to share if you want but of which you’ll unquestionably be done with by the time you hit “send.” It may not be the nadir of Madonna’s career, but I can think of few moments that feel as much like a betrayal of her legacy than the way she deadpans “It’s so erotic” right before chirping “This feeling can’t be beat.” Henderson

78. “You Must Love Me”

We have no particular qualm with Alan Parker casting Madonna as Eva Peron to sell tickets. In the ‘90s, movie musicals just didn’t sell themselves, and they needed any extra help they could get. We also have no problem with Madonna winning the Golden Globe for Best Actress over Frances McDormand in Fargo, an oh-so-Hollywood Foreign Press Association choice that AMPAS even more predictably rendered irrelevant when they didn’t give Madonna an Oscar nomination. If “You Must Love Me” just barely misses taking the dishonor of being ranked the worst of the singles released from the soundtrack, it certainly chides that its entire mad existence was to push Andrew Lloyd Webber that much closer to an EGOT. Henderson

77. “Celebration”

Recorded for Madonna’s 2009 greatest-hits collection of the same name, “Celebration” was clearly intended as a throwback to her early dance anthems. And it’s an embarrassing failure. Producer Paul Oakenfold’s incessant, four-on-the-floor beat may as well have come from a generic EDM sample pack. Worse is Madonna’s beleaguered singing, which sounds like a Gen-Z wannabe’s imitation of the Queen of Pop. “If it makes you feel good, then I say do it,” she tosses off through garish digital vocal effects, coming off like a Real Housewife too sauced on rosé to actually care one way or another. Benny Benassi added some much-needed sonic interest and rumbling bass on the superior remix, which Madonna was at least smart enough to use both for the music video and on tour. Schrodt

76. “Give Me All Your Luvin’”

“Every record sounds the same/You gotta step into my world,” Madonna sings on “Give Me All Your Luvin’,” the lead single from 2012’s MDNA. Even if the song didn’t really sound like anything on the radio at the time, it also didn’t sound like what “Justify My Love” sounded like in 1990, what “Frozen” sounded like in 1998, what “Music” sounded like in 2000, or even what “Hung Up” sounded like in 2005. The song is catchy, sure, but its few charms—‘60s surf-pop guitar, vintage video-game effects, and references to her past songs—are fleeting at best. “Beautiful Stranger,” which shares more than a few similarities with “Give Me All Your Luvin’,” at least sounded like it was being sung by a grown woman rejuvenated and exhilarated by love at first sight. Here, Madonna’s just playing head cheerleader for a team of one—and despite the presence of Nicki Minaj and M.I.A. The issue isn’t Madonna’s age (she’s made a career out of thwarting expectation and convention, which is why she still matters), but authenticity: The difference between, say, “Into the Groove” and “Give Me All Your Luvin’” is that Madonna’s demand for us to give her all our money—err “luv”—is coming from a queen on a throne, not an unknown hipster on the dance floor with the whole world at her fingertips. Cinquemani

75. “4 Minutes”

The 2008 hit “4 Minutes” is so meta—and its creators so egomaniacal—that it wouldn’t be surprising to learn that Madonna and Justin Timberlake actually sat down with the intention of writing a song that could literally save the world and, instead, wound up writing a song about the hassle of writing a song that could literally save the world. Put simply, the song’s lyrics—which at first seemed confusing and muddled to those who expected it to be about, you know, saving the world from climate change or the AIDS pandemic in Africa—seem to attempt to illustrate what it’s like to write or perform a pop song that could actually succeed at doing one of those things, or at making the bourgeoisie and the rebel come together in every nation. Thank God for that colossal, ridiculously infectious horn riff. Without it, “4 Minutes” would be nothing but a busy assemblage of dubious clichés, irritating vocals, and Timbaland’s marching-band beats and irksome “ick-y ick-y” banter. Cinquemani

74. “One More Chance”

Madonna’s ballads are often refreshingly understated compared to those of her contemporaries, her voice homing in on a specific emotional texture rather than bludgeoning you with shrill vocal gymnastics. Though she drifts toward maudlin on “One More Chance,” recorded for 1995’s slow-jam compilation Something to Remember, her pleas for a lover to come back so she can prove her worth are expressive. Regretting her tendency to “play the Queen of Hearts,” however, she sounds downright pitiable. Schrodt

73. “Turn Up the Radio”

Among MDNA’s many disparate attempts at pop relevance, “Turn Up the Radio” is an innocuous but pleasurable enough anthem. The lyrics, aping “Music” without the ironic wit, praise the restorative power of blasting tunes on a drive and forgetting your problems (“We gotta have fun, if that’s all that we do” goes one clunker). In the end, though, Madonna isn’t able to put a distinctive stamp on the track, succumbing to producer Martin Solveig’s relentless beats and supersized bass. Schrodt

72. “Ghosttown”

With its rote production and gratuitous use of Auto-Tune, 2015’s “Ghosttown” is far from one of Madonna’s more searing ballads, but its portrait of a couple’s steadfast commitment even amid the ravages of a post-apocalyptic world feels poignant and relevant, evoking the personal impact of institutional collapse. Schrodt

71. “American Life”

If you can forget that “American Life” contains possibly the worst white-girl rap of all time, rhyming “soy latte” with “double shot-ey” and in the process making Debbie Harry sound like Jay-Z, then it’s actually an admirably gutsy lead single for an album that would effectively end Madonna’s reign on the U.S. pop charts. She and producer Mirwais fuse a dreamy acoustic chorus with harsh skittering drums and laser-like synth sounds, and the disorienting shift reflects Madonna’s state of mind in the lyrics, questioning the demands of the Dream Factory and moving toward something resembling personal satisfaction. It’s pop as bomb-throwing protest. Too bad her list of extensive household staff doesn’t exactly help make the point. Schrodt

70. “Nothing Fails”

Well, nothing like the queen does, anyway. Henderson

69. “American Pie”

Rupert Everett reportedly had to twist Madonna’s arm to convince her to record a cover of Don McLean’s corny karaoke standard “American Pie” for the 2000 rom-com The Next Best Thing. It remains one of the singer’s more dubious covers, yet Madonna—who for so long divined America’s sexual urges—identified the song’s uniquely perverse appeal. McLean’s lyrics mix Christian idolatry and fleshy desires betrayed in a line about a girl who didn’t return his affections at a gym dance. Madonna underlines that tension while flipping the sexual orientation and cutting out the boring parts, seductively stretching out her vowels as producer William Orbit’s gurgling synths intertwine with twangy guitar. Schrodt

68. “Don’t Cry for Me Argentina”

Though her career had been declared dead several times over by 1997, Madonna managed to take a tango-influenced house remix of “Don’t Cry for Me Argentina,” from the film version of Evita, straight to the top tier of the pop charts. With her so-called spiritual and commercial rebirth still a year away, Madonna’s rendition of the song felt like a prelude to Ray of Light’s examination of the illusory benefits of fame and fortune. Cinquemani

67. “I Rise”

“Freedom’s what you choose to do with what’s been done to you,” Madonna sings on “I Rise,” channeling the spirit of Jean-Paul Sartre. The singer has always been loath to play the victim, so the song’s themes of perseverance and self-empowerment are nothing new, but this time they’re directed at contemporary structural oppression and violence, made explicit by a sample of a speech by gun control activist Emma González. The track itself is less affecting than its message, with unnecessary Auto-Tune rendering Madonna’s soaring rhetoric nearly robotic. Cinquemani

66. “Crazy for You”

Among the ‘80s tracks the Madonna fans who were there at the time have a truly curious affection for, “Crazy for You” seems the most curiously inscrutable, though its stately patina instantly calls to mind the carefree California summers of disposable teen flicks. Yes, she was a lot more fun before the Evita vocal training turned her very briefly into Lina Lamont, but boy does this song (reportedly recorded in just one take) highlight just how shaky her singing could be early on. That it also resulted in her first Grammy nomination for best female pop vocal performance calls to mind that bucket of blood hovering over Carrie White’s head. Henderson

65. “Gambler”

“Gambler” is what “Dress You Up” would sound like after six vodka pineapples. Enraged by a series of failed advances, Madonna starts to declare her independence—and with a drunk girl’s sense of absolute self-righteousness. To think what the single (which was released outside the U.S.) could have been had she brought a sneaking sense of vulnerability to what is, at heart, an emancipation proclamation, but it’s an otherwise infectious marriage between Madonna’s assertiveness and John “Jellybean” Benitez’s all-pelvic-thrust production. Ed Gonzalez

64. “Love Profusion”

Leave it to Madonna to recontextualize a love song as social critique. “I have lost my illusions/What I want is an explanation,” she sings on “Love Profusion.” It’s one of the more melodically fetching yet slyly complex cuts from 2003’s electro-folk protest album American Life. Producer Mirwais has a unique gift for using the techniques and structures of contemporary pop but distorting and heightening them until they’re altogether alien. He interrupts the dreamy, acoustic chorus with vocal breaks and harsh wipes that come close to derailing the entire track. Madonna likewise observes the chaos and destruction all around her that threaten to quash her affections, clinging instead to what she knows is right: “Only you make me feel good.” Even the deepest love is always a moment away from ruin. Schrodt

63. Medellín

Named after the city in Colombia where guest vocalist Maluma was born, the lead single from 2019’s Madame X is a sultry midtempo track driven by a decidedly unhurried tropical rhythm. Madonna’s inexplicably Auto-Tune-drenched verses are nostalgic and wistful, nodding to the breezy escapism of “La Isla Bonita.” Vocally, Maluma does most of the heavy lifting on the bilingual track, with innuendo-filled verses that reference both singers’ hometowns, but Madonna’s lush harmonies, particularly during the song’s rousing hook, balance out Maluma’s gigolo routine with a dreamy sweetness. Cinquemani

62. “Miles Away”

While the melody settles for merely being the most tuneful offering from possibly Madonna’s least tuneful album (2008’s Hard Candy), at the heart of “Miles Away” is a genuinely poignant assessment that might well be aimed at both her harshest critics as well as her most demanding fans: “You always love me more miles away/I hear it in your voice, miles away/You’re not afraid to tell me, miles away/I guess we’re at our best miles away.” For a brief moment, you almost imagine she isn’t the type of performer who likes keeping her audience at arm’s length. Henderson

61. “The Look of Love”

If Madonna indeed wrote this European single in part as a tribute to James Stewart’s character in Rear Window, it’s impossible not to wish she’d instead opted for a lilting ode to Norman Bates’s mother. Henderson

60. “Like a Virgin”

Madonna’s iconic “Like a Virgin” may be the first—if not the—signature song of her career, but it’s a trifle—a novelty, really—with its plucky, noncommittal guitar licks, sub-“Billie Jean” bassline, and the singer’s helium squeak of a voice. The song’s vocals were allegedly employed by design, sped up to render Madonna’s voice more childlike and “virginal.” (It’s a trick she’s lamentably reprised on latter-day singles like “Girl Gone Wild.”) Famously not very fond of “Like a Virgin,” Madonna has chosen to completely reinvent the song in masterful ways nearly every time she’s performed it, mercifully rendering it shiny and new by sheer force of will and ingenuity. Cinquemani

59. “Dear Jessie”

What sounds, on paper, like the makings of a cloying nursery rhyme—galloping percussion, giggling children, and psychedelic imagery of pink elephants, singing mermaids, and flying leprechauns—is actually a bittersweet reminder of the ephemerality of our innocence and imagination. A whimsical baroque-pop lullaby punctuated by playful orchestral swells, regal trumpets, and Beatles-esque tempo-shifts, this non-U.S. single is a testament to the magic of Madonna’s collaboration with composer/producer Patrick Leonard. Cinquemani

58. “Living for Love”

The first single from 2015’s Rebel Heart is at once strangely laborious and comfortingly familiar, a straight shot of electro-fried love-as-religion theater that sounds too much like a remix of a true original for it to ever quite cast a lasting spell, nostalgic or otherwise. Gonzalez

57. “Crave”

What Madonna lacks in vocal range, she makes up for with, well, range, adapting her malleable voice to pop, rock, R&B, jazz, and even trap. When she isn’t singing with what sounds like a mouthful of gumballs on “Crave,” the rawness of her voice amplifies the nakedness of her lyrics: “Ran so far to try to find the thing I lacked/And there it was inside of me.” The midtempo ballad juxtaposes acoustic guitar and the singer’s plaintive vocal with 808 snares and a guest verse from rapper-singer Swae Lee. A minor adult contemporary radio hit with pop crossover potential if not for Madonna’s age, the single was, not surprisingly, a club hit thanks to an impressive package of remixes from Tracy Young, Benny Benassi, and others. Cinquemani

56. “What It Feels Like for a Girl”

Occasionally, and only occasionally, Madonna’s reach exceeds her grasp. “What It Feels Like for a Girl” is one of those cases. Its intentions feel more fully fleshed out in the controversial music video than they do in the song itself, with couplets like “Hurt that’s not supposed to show and tears that fall when no one knows/When you’re trying hard to be your best, could you be a little less?” conveying a bit less than Madonna thinks they do, given the conviction in her delivery. But, then again, isn’t the conviction in her delivery entirely the point? Henderson

55. “Hollywood”

From the sound of birds chirping to the track’s bright, jangly guitars and buoyant hook (“Shine your light now/This time it’s got to be good”), “Hollywood” is a deceptively sunny tribute to La La Land. Having effectively retired from acting by 2003, Madonna had some choice words for the town that’s never fully embraced her. But it’s the ire she reserves for the music industry that proved to be most audacious given that even her most recent singles had been played ad nauseam on pop radio and MTV. “Music stations always play the same songs/I’m bored with the concept of right and wrong,” Madonna sings before instructing her audience to “flip the station, change the channel.” Incidentally, “Hollywood” became the singer’s first single in 20 years not to crack the Billboard Hot 100. Cinquemani

54. “Beautiful Stranger”

Madonna has always been incredibly savvy about zigging when she’s expected to zag. Recorded for 1999’s Austin Powers: The Spy Who Shagged Me soundtrack, “Beautiful Stranger” was in many ways the antithesis of Ray of Light, despite sharing producer William Orbit. The hooky, psychedelic track is more accessible than Madonna’s previous work with Orbit. The innocuous lyrics could’ve been ghostwritten for anyone—“I looked into your eyes, and my world came tumbling down”—but the song endears due to Madge’s playful delivery and Orbit’s sonic details. Schrodt

53. “Causing a Commotion”

Somehow generic and diverting in equal measure, “Causing a Commotion” offers one of Madonna’s most undeniable come-on lines at the center of it all: “I’ve got the moves baby, you got the motion/If we got together we’d be causing a commotion.” That “if” indicating that, no, in fact they aren’t currently together goes a long way toward explaining how the surrounding music is more promise than follow-through. Henderson

52. “Die Another Day”

In the midst of her third or fourth commercial wind, Madonna could have released a grating, electroclash 007 theme song and still cracked the Top 10. And that’s exactly what she did. By 2002, Esther was at the height of her Kabbalistic explorations, and “Die Another Day”—which expounds on the metaphysical properties of the human ego—is an exercise in withholding: an ostensible pop song with a deconstructed hook, a cinematic orchestral arrangement that’s hacked up and reassembled, and the voice of the biggest pop star in the world rendered barely recognizable. It’s innovative, frustratingly anticlimactic—the aural equivalent of edging—and, perhaps fittingly, the last in Madonna’s long string of soundtrack hits. Cinquemani

51. “Who’s That Girl”

Not quite as relentlessly cloying as my younger self thought it to be—some calorie-free palate cleanser after the delectable voluptuousness of “La Isla Bonita.” Today, the music is catchy without ever stepping outside any norm. More interesting is that friction between object and objectifier that escalates throughout and reaches its peak in the call and response of the chorus, which feels almost poignant in light of Madonna, more than 30 years later, not appearing any closer to being able to answer the rhetorical question of the song’s title. Gonzalez

50. “I Don’t Search I Find”

It might be a thrill to hear Madonna singing over a ‘90s house beat again on the smoldering “I Don’t Search I Find,” which searched and found its way to the top of Billboard’s club chart in early 2020. But despite its ballroom strings, finger-snaps, and throaty spoken-word bridge, comparing the track to “Vogue” or “Erotica” would be too easy. This isn’t a song so much as a mood. It’s downstairs music, the distant bassline rumbling beneath your feet as you slip into a bathroom stall for a quick bump or fuck. Cinquemani

49. “True Blue”

Truly, the questionable lure of turning the clock back to the sock hop escaped no one in Reagan’s America, and credit to Madonna for turning out one of the more tolerable doo-wop pastiches, buoyant without being entirely weightless. Henderson

48. “Angel”

The ultimate “this is better than I remember it” single of Madonna’s career, “Angel” is best half-remembered, the better by which to keep rediscovering it again and again. Which is to say, keep this “Angel” in pop purgatory. Henderson

47. “You’ll See”

Though Madonna has proven herself a capable singer over the years, what she lacks in power or range she makes up for with nuance and feeling—something the most celebrated vocalists of her generation have been accused of lacking. This is no more apparent than when you compare her performance of her 1995 hit ballad “You’ll See,” on which she conveys both the smoldering melodrama and stoic sorrow of a woman scorned, to cover versions that have been recorded by ostensibly superior singers like Shirley Bassey and Susan Boyle. What feels complicated and layered in Madonna’s hands is rendered mere fodder for chest-pounding theatrics. Cinquemani

46. “Give It 2 Me”

Pharrell’s production on 2008’s “Give It 2 Me” cleverly employs modern hip-hop sounds while nodding to the soul, funk, and disco greats who paved the way for both him and Madonna. To wit, the nearly five-minute track builds from snare drums and crescendos with blissful arpeggio synths as the singer, then 25 years into her career, cheekily references her indomitable ambition. “If it’s against the law, arrest me,” she taunts. “I can go on and on and on.” And it turns out she can, with an addictively moronic interlude in which she commands the listener to “get stupid” while Pharrell, ever the sonic prankster, breaks in from the left speaker, then the right. This is ass-shaking music with Olympic-sized stamina. Schrodt

45. “Love Don’t Live Here Anymore”

Originally recorded in 1984, Madonna’s cover of the classic soul song “Love Don’t Live Here Anymore” was remixed and (bizarrely) released as a single 12 years later in support of the singer’s ballads collection Something to Remember. Among Madonna’s more faithful covers, her rendition of the Rose Royce song doesn’t fuss with the original’s elegant songwriting and emotional force. She wisely relies on a tearful, angsty rock delivery as the track builds and the strings undulate, belting the last “anymore” until she’s literally panting for breath. Schrodt

44. “Bye Bye Baby”

“This is not a love song,” Madonna insists at the start of “Bye Bye Baby,” the final single from 1992’s Erotica. But it’s just wishful thinking: One particularly vengeful line from the song, “I’d like to hurt you,” takes on new meaning following the singer’s revelation that “I only hurt the ones I love” on the album’s title track. The vocal filter throughout “Bye Bye Baby” gives the effect of an answering machine message, the bleep that censors Madonna’s final barb—“You fucked it up”—doubling as the machine’s end-of-message beep. Cinquemani

43. “Drowned World/Substitute for Love”

After collaborating with Massive Attack on her 1995 cover of Marvin Gaye’s “I Want You,” Madonna was reportedly eager to sing on a track that would eventually become “Teardrop.” Elizabeth Fraser of the Cocteau Twins ultimately snagged the part, but the trip-hop pioneers’ influence can be heard on the autobiographical opening track of Madonna’s 1998 album Ray of Light. Layered with vocal samples and buoyant drum n’ bass beats, “Drowned World/Substitute for Love” (which was released outside the U.S.) sums up the singer’s personal tribulations with fame and, perhaps coincidentally, the pitfalls of getting what you want: “I got exactly what I asked for/Running, rushing back for more…And now I find, I’ve changed my mind.” Cinquemani

42. “Everybody”

It’s almost impossible to think of Madonna as she was on her first single, “Everybody”: a faceless voice so understated it would be inaccurate to say it’s that of a diva—post-disco or not. The Mark Kamins production sparkles with shiny-and-new-for-1982 synths, while Madge offers a preview for the world-as-a-dance-floor motif she’d never stop revisiting throughout the next three decades years. “Everybody” preceded Madonna’s media saturation, the vital balance she’d come to strike between the musical and the visual and her own gigantic persona. As tracky as Madonna has ever been, “Everybody” stood on its music alone. And, really, it was a good look for her. Rich Juzwiak

41. “Take a Bow”

A noticeable sadness pervades Madonna’s 1994 album Bedtime Stories, which found the singer at her softest and most vulnerable. Her bittersweet vocal turn on the album’s biggest hit, “Take a Bow,” is at once despondent and quietly indignant. Despite producer Kenny “Babyface” Edmonds’s unmistakable (and then-ubiquitous) R&B sound, the track is surprsingly durable, its understated charms still apparent decades later. Though Madonna journeyed to Spain to shoot the single’s cinematic music video, the song’s gently cascading refrain and theatrical string arrangement have a distinctly Asian flair, distinguishing it from the cookie-cutter ballads Babyface was churning out at the time. Cinquemani

40. “Get Together”

With a mix hot enough to make it sound like the tune is literally sweating right along with you as you writhe together on the dance floor, “Get Together” has clearly taken that hit of MDMA, stringing along non sequiturs about believing in love at first sight, changing the future, and making everyone feel better, all of them making total sense in the context of being overwhelmed by the hot beats and cool synth sheen coming from the perfectly calibrated speakers. Henderson

39. “Dress You Up”

Girlish consumerism with nary a wink in sight, “Dress You Up” didn’t even have to be co-opted to fit right into a Gap advertising campaign years later. In retrospect, we all should’ve been a little more skeptical of a song whose entire lyrical content consists of assurances that custom-made suits and satin sheets against the skin are no match for Madonna’s naked body, coming as it did during the era in which she made it her mission to simultaneously wear every single fabric known to man. Henderson

38. “Jump”

Paced about a half-dozen BPMs slower than a disco gallop—giving the impression of a DJ pitch-shifting a familiar chestnut to give it a blue, after-hours glow—“Jump” doesn’t exactly act like it hasn’t “got much time to waste.” Which is one of the reasons why it, like all of Confessions on a Dance Floor’s singles, is such a great dance song. Nothing really matters except for the groove, and the all-too-brief amount of time any of us get to share with it. A love note from Madonna to everyone who is, as a matter of fact, always ready to jump. Henderson

37. “Hanky Panky”

An unlikely hit single, from an unlikely source: an album that’s only nominally a soundtrack. Inspired by Warren Beatty’s Dick Tracy only insofar as Madonna’s character from the film, Breathless Mahoney, is a femme fatale cum showgirl with a dangerous sense of seduction, I’m Breathless is one of the pop star’s finest games of hide and seek. “Hanky Panky,” better than any of the three good but persnickety Steven Sondheim tunes on the album, is straight out of the gate a ballast of campy subversion. It’s a song about spanking in the swing style of the 1930s, and it still sounds like one of the most delicious and improbable novelties of Madonna’s career. Gonzalez

36. “This Used to Be My Playground”

Recorded during the Erotica sessions for the Penny Marshall film A League of Their Own, this quietly sublime ballad is an outlier among Madonna’s more confrontational early-‘90s output. The song’s understated production—soft percussion, lilting keyboards, and cinematic orchestral arrangement—recalls Madonna’s earlier ballads. The strings complement her aching vocal, rising to a dramatic moment in the bridge, without ever becoming treacly. Madonna’s lyrics nail the push and pull between nostalgia and the inevitable disappointment that comes with retracing one’s steps. “Don’t hold on to the past,” she sings, defeated. “Well, that’s too much to ask.” Schrodt

35. “Bad Girl”

On an album that is, without question, Madonna’s finest gay moment, “Bad Girl” stands out as a moment of high drag, a brutal self-laceration served in the most flamboyantly melodramatic fashion imaginable. On those terms, its only real rival on Erotica is the George Gershwin-swiping funereal AIDS dirge “In This Life,” but “Bad Girl” is the far more dangerous track, slipping into the death drive as though expecting tips. Her perilous journey is driven home, in a post-drunken stupor, by Shep Pettibone’s pitilessly spare backdrop and slow-motion car wreck of a bassline. Henderson

34. “Keep It Together”

Like a Prayer firmly ensconced Madonna in the rock canon. The richly layered album stretched her sound in more than one way, however, and on the Sly and the Family Stone-inspired “Keep It Together,” she convincingly took on pop-funk. The slap bass and jangly guitars (courtesy of an uncredited Prince) make this one of the more upbeat, hummable listens on the album, but it’s no less packed with feeling. Madonna’s affirmation of family bonds is uncharacteristically sweet and vulnerable: While she’s alluded to a strained relationship with her father over the years, she pays tribute to their deep bond with a heartening reminder, especially in the wake of her divorce from Sean Penn: “Daddy said, ‘Listen, you will always have a home.’” Schrodt

33. “The Power of Good-Bye”

Upon the release of Ray of Light, genre purists scoffed at the idea that what Madonna had made could be called an electronica album. The suggestion that it was merely pop music dressed up with digital flourishes wasn’t completely off the mark, nor was it a damning critique. After all, delivering underground culture unto the masses had become Madonna’s m.o. Structured like your average adult-contemporary ballad—the song was co-written by Rick Nowels, most famous for his work with Belinda Carlisle and Stevie Nicks—and featuring a richly layered arrangement of acoustic guitars, sweeping strings, and lush atmospherics, “The Power of Good-Bye” is quintessential electronica-lite. And it goes down as smoothly now as it did in 1998. Cinquemani

32. “Burning Up”

The most aggressive song on Madonna’s 1983 debut hints at her pre-fame days as a rock singer and drummer in the band the Breakfast Club. The electric guitar crashes in over the tight, syncopated beat like an alternate take from Kenny Rogers’s “Danger Zone.” Corny, sure, but Madge’s shameless panting for a man’s affection and threat to get on her knees and “do anything,” punctuated by a high synth line, don’t betray a single wink. This is the height of Top 40 kink. Schrodt

31. “Sorry”

More ABBA-esque than the ABBA-sampling “Hung Up,” the unapologetically Euro second single from 2005’s Confessions on a Dance Floor scored Madonna another worldwide smash (though the U.S., in the midst of another hip-hop fixation, largely ignored it). Madonna is notorious for not being the apologetic type, so, if nothing else, “Sorry” gave Camille Paglia a chance to hear her say it in 10 different languages. Cinquemani

30. “Rescue Me”

Released at the height of Madonna’s imperial phase, 1990’s “Rescue Me”—one of two new songs on her blockbuster greatest-hits album The Immaculate Collection—merged the spoken-word style of her most previous hit, “Justify My Love,” with producer Shep Pettibone’s contemporary house beats. Madonna’s throaty spoken verses indulged her penchant for poetry and self-analysis—“With you I’m not a fascist/Can’t play you like a toy/And when I need to dominate/You’re not my little boy”—while the track’s soulfully belted choruses flaunted both the singer’s developing vocal prowess and her enduring knack for instant pop hooks, landing the song in the Top 10 when it wasn’t even intended to be a single. Cinquemani

29. “Borderline”

Has there ever been an opening refrain more winsome and instantly nostalgic than that of Madonna’s first Top 10 single? Those tender chords flawlessly establish the tranquility of life before a torrid and, from the sound of it, toxic affair. And even after they’re interrupted by aerobic drum patterns and pitch-flexible synthesizer hooks, they linger in the memory, a haunting reminder of a youthful summer forever lost to an ill-advised love. Henderson

28. “Cherish”

“Cherish” is a beacon of light, a spritely and slyly referential dollop of “True Blue”-esque doo-wop swimming atop the engorged baroque pop that is Like a Prayer. The song’s radiance stems from Madonna’s sense of foresight—her understanding that this might just be her last chance at conveying such a sweet and uncomplicated sense of joy. It’s as if she can see the more duty-bound chanteuse of Erotica waiting to step in to rewrite the story of Romeo and Juliet in the context of an era, unlike this one, that’s less complacent about how our fears have hijacked our desires. Gonzalez

27. “Nothing Really Matters”

“I’m no fucking Buddhist, but this is enlightenment,” Björk declared on “Alarm Call,” released just a few months prior to Madonna’s “Nothing Really Matters.” Both songs juxtapose their iconic creators’ discovery of universal truths with joyous house beats—they’re the most straightforward dance-pop offerings of their respective landmark albums—though Björk’s sense of awe is, notably, complemented by her wry sense of humor. Lyrically the most elementary of Ray of Light’s earnest spiritual lessons, “Nothing Really Matters” chugs along with revelatory abandon—yes, adorned with producers William Orbit and Marius De Vries’s skittering electronic noise and wobbly burbles, but also a bouncy bassline, infectious beat, and the most exhilarating piano break in a Madonna song since the extended mix of “Into the Groove.” Cinquemani

26. “Bedtime Story”

A prelude to Ray of Light both in terms of its sonic influence, but also its spiritual explorations, 1994’s “Bedtime Story” provided a bridge between Madonna’s early-‘90s house and late-‘90s electronic excursions. Co-penned by Björk, the track is a hypnotic, druggy exploration of the limitations of communication, and Madonna’s adoption of the Icelandic artist’s meticulous pronunciation throughout underscores that theme. But where Björk often brings a brainy intensity to dance music, Madonna is instinctive, and she imbues lines like “Inside we’re all still wet” and “Let’s get unconscious, honey” with a cool sensuality that’s very much her own. The track is conspicuous among the lush R&B of Bedtime Stories, but when Madonna declares, “I’ll never explain again,” at the song’s end, it dovetails flawlessly with the album’s thematic thread, the closing—or is it the beginning?—of a chapter in the singer’s own story. Cinquemani

25. “Don’t Tell Me”

Madonna’s Y2K-era dalliances with electronica could oftentimes verge on the theoretical, and “Don’t Tell Me” is engrossed in chemistry-set beat science. The track is first and foremost a concoction: two parts corn pone, one part glitch, with reliable disco strings to serve as the catalyst. What seals the deal, though, is that lyrically Madonna’s on board too. Tell the peanut butter of acoustic guitars to stay away from the chocolate of digital bass drones, but don’t tell Madonna she can’t eat both and spit back manna. Henderson

24. “Material Girl”

There is, perhaps, no better testament to the holistic nature of Madonna’s work than “Material Girl,” whose music video fundamentally changed the meaning behind what, in another artist’s hands, would likely have been a straight-faced tribute to Reagan-era avarice. An infectious bop punctuated by the singer’s girlish vocal hiccups and producer Nile Rodgers’s playful synths, the track is as frothy and frivolous as its subject matter. That Madonna would forever be referred to as the Material Girl is, likewise, a testament to the press’s persistent inability—or refusal—to acknowledge the irony in almost everything she does. Cinquemani

23. “Music”

From its pointedly generic title to Madonna’s anonymous vocal performance, “Music” is a blank canvas of a song—a tribute to the accessibility and universality of the titular mode of communication. To wit, the song has had almost as many makeovers as Madonna herself, from 1970s disco during her Confessions Tour, to ‘80s hip-hop during her Sticky & Sweet Tour, to, most recently, roaring-‘20s jazz during her Rebel Heart Tour. If music truly is a universal language, then “Music”—in all of its meta reinventions and retro dialects—might be the best piece of evidence we have that music really does make the people come together. Cinquemani

22. “Fever”

The final track to be recorded for Erotica, Madonna’s cover of “Fever”—the result of an impromptu moment in the studio while laying down vocals for another song—almost never happened. Which is ironic given that “Fever”—with its precise horn stabs, sleek string pads, and pulsating beat—is the closest she and producer Shep Pettibone ever came to recreating the clean, crisp house aesthetic of their massive 1990 hit “Vogue.” It’s Madonna’s performance, however, that’s the real star here: Unlike on much of the album, her voice cuts through Pettibone’s chilly backing track like a hot knife through butter. She may lack Peggy Lee’s command, but Madonna exudes a detached confidence and control that is the pitch-perfect embodiment of Erotica’s main thesis: love hurts. Cinquemani

21. “Papa Don’t Preach”

“Papa Don’t Preach” may well be the only song about choosing not to have an abortion that also feels rebellious, even dangerous. The 1986 chart-topper’s cinematic string arrangement gives a sweeping backdrop to a theatrical monologue, in which Madonna—or rather, her character, a Staten Island teen—decides to keep her baby despite social and familial pressures to do otherwise. Madonna has rarely sounded more impassioned, coming clean to a father figure with forthright earnestness. Schrodt

20. “Lucky Star”

“Lucky Star” sets the tone of Madonna’s debut album right off the bat, with shimmering, programmed glissandos that soon give way to clanging rhythm guitars, synth atmospherics, and chugging bass. A sonic monster worthy of David Mancuso’s fine-tuned system at the Loft, and balanced with a chorus built around a childhood mantra and delivered via helium-tinged vocals, “Lucky Star” established Madonna as a one-woman girlie show in a genre more comfortable with full-throated divas. Henderson

19. “Holiday”

The genius of Madonna’s early, post-disco work is how it does so much with so little. With “Holiday,” the singer gives space to an immaculate arrangement featuring cowbell, guitar, synths, and Fred Zarr’s keyboard solo, which together comprise the track’s funkiness and simple melodic pleasures. But Madonna’s soulful vocal take, ushering in a celebration “in every nation” as if she were taking on the world’s problems as her own, is what’s made this hit outlive its seemingly superficial charms. Schrodt

18. “I’ll Remember”

Like “Vogue,” Madonna’s long-legged 1994 hit “I’ll Remember” represented one of the most important gear-changes in her entire career. An underwater indigo dirge featuring a remarkable below-the-root bassline and supple, husky vocals, “I’ll Remember” settles up the score following the widely (and wrongly) derided Sex era and finds Madonna switching Who’s Afraid of Virginia Woolf? roles mid-performance from “hump the hostess” Martha to “I wanna have a baaay-bee” Honey. It’s the key to understanding how both Lourdes and Ray of Light came into being. Henderson

17. “Human Nature”

“Oops, I didn’t know I couldn’t talk about sex/I musta been crazy,” Madonna quips on “Human Nature,” the final single from 1994’s Bedtime Stories—and the singer’s final word on her Sex period. For years, Madonna spoke in metaphors, fantasies, and blatant shock tactics, but with “Human Nature,” she indignantly struck back at her critics in a rather straight-forward manner: “I’m not your bitch/Don’t hang your shit on me.” She wasn’t just holding up a mirror, she became the mirror: “Did I say something true?…I didn’t know I couldn’t talk about you.” Madonna suggests her opinions on sex would have sounded better if she were a man. Different, sure. But better? Nah. Cinquemani

16. “Rain”

Released alongside her scandalous Sex book, 1992’s Erotica was unfairly maligned for being sex-obsessed. While songs like the title track and “Where Life Begins” unapologetically indulge in a woman’s carnal desires, the album also thoughtfully plumbs the depths of Madonna’s heartache. The song’s titular metaphor signals not only sexual pleasure, but rebirth—a more spiritual, holistic cleansing. The bridge’s clattering drums and dissonant synths interrupt producer Shep Pettibone’s otherwise tranquil arrangement, and Madonna, connected to the forces of nature, finds peace after the storm. Schrodt

15. “La Isla Bonita”

Co-written and produced with Patrick Leonard in what would become a long and arguably her most fruitful working relationship, “La Isla Bonita” finds Madonna wistfully longing for an island that’s essentially a stand-in for all of Latin culture. But the singer’s ethnic tribute is more than just fetishistic, conjuring a dream of a faraway paradise that, unlike earthly destinations, might welcome anyone under its sun. Meanwhile, Leonard’s sneakily complex arrangement—Spanish guitar, Cuban drums, maracas, and emphatic blasts of brass—gave a dynamanism to Madonna’s music that finally perished the thoughts, based on her earliest hits, that she was simply a Danceteria pop tart. Schrodt

14. “Secret”

Despite the common misconception that she often sings about sex, Madonna’s songs aren’t always sexy. “Secret,” the lead single from 1994’s Bedtime Stories, is perhaps the finest exception to that rule. As it slinks along a simple R&B backbeat and an unfussy acoustic guitar figure, “Secret” is also one of the most organic-sounding singles of Madonna’s career, taking its sweet time to get where it’s going and not giving up too much along the way. The arrangement gets off on being withholding, and, at least for one glorious single, so does Madonna: When she sings, “You knew all along/What I never wanted to say,” she sounds positively rapturous. Jonathan Keefe

13. “Hung Up”

“Hung Up” employs a ticking clock to represent fear of wasted time, but Madonna isn’t singing about aging or saving the world—she’s talking about love. Coming on the heels of the spiritual musings of Ray of Light and the pedantic socio-political posturing of 2003’s American Life, “Hung Up” was decidedly vapid. With its pitched-upward vocals, infectious arpeggio sample from ABBA’s “Gimme Gimme Gimme (A Man After Midnight),” and the bridge’s unironic, archetypical key change, the track points to the past, and it proved that, 20 years into her career, Madonna was still the one and only Dancing Queen. Cinquemani

12. “Justify My Love”

This unlikely 1990 smash hit’s deep, throbbing bass and cooing backup vocals (courtesy of co-writer and producer Lenny Kravitz) provide the minimalist structure for Madonna’s largely spoken-word lyrics. She declares her lust and love with a jarring frankness that foreshadowed Erotica, coaching an unspecified lover through her highly specific fantasies. That the focus is solely on her “wanting, needing, waiting” of course helped prompt the misogynistic backlash to Madonna’s sexually provocative ‘90s output. Even in this supposedly enlightened age, however, what’s most striking here is her vulnerability. “So now what?” is not only a challenge, but a serious existential question directed at both her partner and herself that speaks to her thirst for all that life has to offer, orgasmic or otherwise. Schrodt

11. “Ray of Light”

Once Madonna made it her mission to bring electronica to the masses, she had her pick of collaborators. Her decision to work with William Orbit shows that, for all the flack she’s faced for “appropriation,” her interest in underground dance music is deep and not wholly commercial. Madonna discovered techno just as she turned 40 and took up Kabbalah, and listening to 1998’s “Ray of Light,” it’s easy to imagine her finding in rave culture not just a new image, but a way of expressing her spiritual awakening. The beat is restless and Madonna sings breathlessly, but she exudes contentment: “I feel like I just got home!” Her emotional warmth is what establishes the song as a standout single even in a catalogue as replete with classics as this. Matthew Cole

10. “Frozen”

If “Frozen” is impossible to separate from the gothic chic of Chris Cunningham’s music video, that’s because the song itself is a series of conspicuously alluring affectations. Atop a snaky, string-laden electronic landscape that’s transfixing in no small part because of how brazenly it grasps at the exotic, Madonna serves Grimes-going-to-the-Met-Gala realness. Her vocals are at once naked and withholding, a tango of warring impulses that are obligingly whipped up by the electro-symphonic flourishes of William Orbit’s production. Gonzalez

9. “Erotica”

Madonna’s throaty voice circa 1992 makes Erotica’s taunting, aggressive lyrics—an elaborate exploration of sex, from seduction to disease—feel unmistakably honest. The album’s title track, whose opening scratchiness mirrors that of Madonna’s instrument, is the singer’s invitation to the dance, a slithering, sinister snake rising from a gaudily ornate chalice. The beats are, by design, hypnotic—at once alluring and devious. With “Erotica,” Madonna promises to get you off—but not without giving you something. Gonzalez

8. “Oh Father”

If “Oh Father” doesn’t touch the pop-gospel magnitude of “Like a Prayer,” on which the choir endows Madonna with strength and confidence, that’s by design. On this baroque-pop inversion of the Lord’s Prayer, the singer seeks those things out for herself. If Patrick Leonard’s production is genteel, that’s because it exists to cede as much power to Madonna as possible. It’s not the track’s soaring violins or Donna De Lory and Niki Haris’s cherubic background vocals that do the heavy lifting here, but the wounded charge of Madonna’s sense of remembrance, which is so acute as to carry her into a realm of spiritual salvation. Gonzalez

7. “Open Your Heart”

David Byrne once sang, “Watch out, with that attitude you might get what you want,” and it feels as if Madonna has made a career of realizing that ambition by any means possible. It’s funny to think that “Open Your Heart” could have ended up with someone other than the Material Girl. Yes, Cyndi Lauper might have spun something altogether more poignant from this unabashedly sincere and playfully metaphoric love song, but the conviction Madonna reveals throughout, as exhaustible as Patrick Leonard’s fluttering rock-dance bassline, finds her in a strikingly confessional light. As in the song’s polar opposite, 1993’s “Bye Bye Baby,” an anti-love song in which she coyly makes the man do the chasing, Madonna was and always will be credible only at her most naked. Gonzalez

6. “Deeper and Deeper”

The angsty house anthem “Deeper and Deeper” is both an acute distillation of Erotica’s smut-glam decadence and Madonna’s lifelong blond ambition. The song, like its video, practically plays out as an autobiography of the singer’s life: Atop sambalicious disco, she delivers a burning, poignant fairy tale of yearning and escape in which she plays both Little Red Riding Hood and the Big Bad Wolf. Armond White once praised Madonna for how she took “outsider art inside herself”—which is to say, justified it by personalizing it. The uncontrolled, fierce tension of “Deeper and Deeper” derives from the feeling that Madonna is taking a plunge into some hedonistic abyss of her own liberated, uninhibited making. Gonzalez

5. “Live to Tell”

Madonna’s first and, arguably, most dramatic reinvention was scored by the spare and haunting ballad “Live to Tell,” which wasn’t just a daringly demure introduction to her third album, 1986’s True Blue, but also posed a challenge to pop-radio programmers keen on instant gratification: The song begins with almost a full minute of music before the singer starts to tell her tale, and includes abrupt key changes and a half-minute midsection in which nearly all of the music drops out. Of course, it worked like a charm, and “Live to Tell” launched a fruitful professional relationship between Madge and producer Patrick Leonard that would last for more than two decades, and set the stage for the fearlessly autobiographical material to come. The song features one of Madonna’s richest vocal performances, full of soul, yearning, and hurt, with lyrics that can surely resonate with anyone who’s ever endured a detention of silence—self-imposed or otherwise. Cinquemani

4. “Express Yourself”

It was David Fincher’s Metropolis-inspired music video for 1989’s “Express Yourself” that introduced the world to Shep Pettibone’s remix, which, aside from the lethargic come-and-git-it cowbell that intermittently takes Madonna from the church steeple and straight onto the prairie, matches in its uptempo beat the soulful fervor of the singer’s call to arms. The album version evokes something altogether more subversive: Fritz Lang’s robot Maria hanging out inside a Detroit dance hall, forcing men to their knees as the big-band sound rocks the house. But it’s Pettibone’s reconstruction—which replaced producer Stephen Bray’s Sly Stone-indebted soul with sleek strings and a muscular house beat—that helped announce the arrival of Madonna the power feminist and set the stage for both “Vogue” and Erotica. Gonzalez

3. “Into the Groove”

On her very first single, “Everybody,” Madonna beckoned to the boy sitting on the sidelines to come dance with her but stopped just short of inviting him to touch her body. On “Holiday,” Madonna posited “the dance” as a venue for social change—or, at least, an escape from the bleak reality waiting on the fringes of the dance floor. With 1985’s “Into the Groove,” however, she’s unapologetically single-minded: It’s love she’s looking for, not just a dance partner. It’s hard to imagine the world’s most famous exhibitionist dancing alone in her bedroom at night, locking the doors so “no one else can see,” as she sings here, but you can’t help but believe her. The song—and Madonna’s performance—are that good. Music can be a revelation, indeed. Cinquemani

2. “Like a Prayer”

With an atypical structure in which the drums drop out completely during each verse and the chorus is all but abandoned halfway through the song in favor of ad libs and gospel choiring, what’s now considered a perfect pop song seemed more fit for a church than Top 40 radio at the time. Though she’d evoked religion before, most notably with heaps of rosary beads dangling between her décolleté, it was, perhaps, inevitable that with a name like Madonna, the so-called Material Girl would more seriously explore the faith with which she was so strictly raised. But while there have been about as many interpretations of the song’s lyrics as there are remixes—she’s singing about God, she’s singing about giving a blowjob, she’s singing about giving God a blowjob—“Like a Prayer” begs for a more refined reading than a conflation of spiritual and sexual ecstasy. Cinquemani

1. “Vogue”

“Vogue” falls in line with a startling arc of growth and self-consciousness of which “Express Yourself” was the warning shot, an unmistakably feminist missive that explicitly excluded straight males from its directive and then commanded they respond to its demands. From telling straight women and gay men that their love has every potential to be real, Madonna then submitted her persona within the gay identity with “Vogue.” If some found her cultural appropriation presumptuous, the reward was in the music you could let your body move to, hey, hey, hey. At least so far as pop music is concerned, “Vogue” was instrumental in allowing disco revivalism to emerge, allowing the denigrated gay genre to soar once again within the context of house music, which was the genre disco became in its second life. Henderson

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