To adopt that old cliché; Madonna needs no introduction. As chameleonic as Bowie, her 36 year career has seen her deftly switch from scrappy punk hopeful to earnest balladeer; from relentless dominatrix to chaste earth mother and back. She’s responsible for some of the most memorable pop moments of the last 40 years: from the burning crosses of “Like a Prayer” to her VMAs kiss with Britney Spears, it’s hard to imagine a pop cultural landscape untouched by her audacious iconoclasm. A voracious pop cultural maven, she stole from Gentlemen Prefer Blondes and the New York City vogue scene and (however problematically) remade it all in her own image. Lyrical threads of sex, dance, and religion run through her entire back catalogue. A quintessential Leo, she’s always self-assertive, always innovative.

It’s rare to find a pop fan or music critic whose life hasn’t at some point been touched by her music, and we at The Singles Jukebox are no exception. To celebrate her 60th birthday, we take a look back at a greatest hits arguably unparalleled in recent pop music history.

Matias Taylor on “Everybody” [6.42]

Madonna Louise Ciccone arrived in New York City in 1978 with dreams of becoming a professional dancer, leaving behind a scholarship to the University of Michigan (her professors told her she didn’t need it) and promising herself to never return to the strict Catholic small town life she had been raised in. The next few years would be a mixture of crummy apartments, part time jobs (she got fired from the Russian Tea Room for wearing fishnets to work), and gruelling auditions, one of which led to the suggestion that she should also try singing. This, in turn, led to a stint with singer Patrick Hernandez’s producers, who promised to “make her a star”. Like most things in Madonna’s career, she figured out a way to do it for herself, and better than anyone else could have. A few punk rock bands later, after discovering that she could write her own songs, Madonna found herself signed to Sire Records and also found her sound: a synth-laden, post-disco style of dance pop that drew from R&B artists like Kool & the Gang and Michael Jackson (she was often called “the female Michael Jackson” by the press during her first few years).

“Everybody” was the first offering from her self-titled debut album, and the world’s first introduction to Madonna, music video and all. It was not a hit, failing to chart on the Billboard Hot 100, but it was a success in New York City clubs such as the legendary Danceteria, where Madonna was hanging out with luminaries like Jean Michel Basquiat, Andy Warhol, and Keith Haring. “Everybody” sounds like it was meant to be animated by the latter’s signature humanoid cartoon figures; the shimmering synth and punchy bass line wobble their way through five minutes plus, and they’re hypnotic enough that the track needs little else. The simple lyrics, a beckoning to the dance floor, would prove to be the blueprint for one of the central themes in Madonna’s work: music’s ability to draw together disparate crowds in a unifying energy, with dance as a medium for self-expression and liberation.

“Everybody” is perhaps a footnote in her discography at this point, the false-start first single that would later be overshadowed by the massive breakout smashes of her early ‘80s period, but it’s an irresistible confection that relishes its straightforwardness and showcases Madonna’s spectacular ear for a hook; and as her next 30 plus years of world-conquering pop music show, that ear just might be the most important weapon in her arsenal.

Jibril Yassin on “Burning Up” [7.09]

I heard “Burning Up” for the first time on Celebration, and as much as I regret spending significant time with that compilation, I have yet to regret any moments spent playing air guitar to the cheesy solo. It’s early Madonna – fun, endearing, genuine and ridiculous. Where songs like “Holiday” and “Borderline” feel frozen in amber, just about perfect in every way, “Burning Up” delights in being messy. The guitar flits in and out of the track, leaving us alone with one big beat and a Madonna somehow sounding both incredibly vulnerable and bolder than anything you have ever heard before. She zigged when you’d expect her to zag – brash when you were hoping for sweet. Buried in the song’s middle eight is the ethos for her entire career: “Unlike the others, I’d do anything. I’m not the same. I have no shame.” You could likely apply that to just about any thrilling career move that came after her self-titled took off. That’s why “Burning Up” is an essential snapshot of early Madonna – one who was still figuring it out.

Thomas Inskeep on “Physical Attraction” [6.55]

I miss the old Madonna: the Madonna who wasn’t a great singer (i.e. pre-pre-Evita vocal training), the one who was unapologetically kinda trashy, the one who didn’t have a weird Tina Turner-esque pan-Euro accent, the one who dressed like the sale rack at Trashy Lingerie – the Madonna of Madonna, her 1983 debut album. That’s the Madonna on display in this fan-made video for the “Burning Up” b-side “Physical Attraction,” which is my single favorite Madonna record. Written and produced by the late Reggie Lucas (Miles Davis, Mtume, Stephanie Mills) and remixed by John “Jellybean” Benitez, this is all Linn drums and fat-ass synth bass, but most of all, it’s all Madonna. This song would’ve been nothing without the future Queen of Pop spraying it down with her hunger and attitude. She sings “Physical Attraction” like her life depends upon it, because she knew it did. This was her shot, and she made it count. From the opening line, “You say that you need my love/And you’re wanting my body, I don’t mind,” this song is essentially the template for the first decade of Madonna’s career: she laid it right out there for us.

Josh Love on “Holiday” [7.92]

“Holiday” was a late addition to Madonna’s debut album; an outside contribution written by members of the disco group Pure Energy, and scooped up by producer John “Jellybean” Benitez in the hopes of feathering the record’s nest with a potential hit single. That gambit worked; it was Madge’s first big hit (#2 in the UK). It’s a wondrous song and one of her undying classics, yet it’s probably for the best that other hits from her eponymous first effort followed, because “Holiday” is quite an anomaly among those early tunes, at least lyrically. Sex and romance were front and center from the beginning for Madonna – even the groove exhortation “Everybody” is deeply physical – but “Holiday” casts her in the role of antiseptic cheerleader rather than heartfelt romantic or lust-filled dancefloor queen. Down that road lies the remains of lots of one-hit wonders, especially during the disco/post-disco era. Once the Material Girl made it clear she’d be assembling a legacy indelibly stamped with her own voice, ideas, and peccadilloes, “Holiday” could simply stand as a great, carefree pop song, an eternal crowd-pleaser colored with silly synth squiggles between the verses, driven by itchy, Chic-ish guitars and topped off with a marvelously indulgent piano solo.

Jacob Kuppermann on “Lucky Star” [7.50]

“Lucky Star” is the first Madonna song to even hint at the grandeur and pomp that her music would develop as her albums went on – the celestial motifs aren’t particularly developed, but they’re here in force, clearer in the gleaming perfection of that introductory synth loop more than in any of the lyrics. But the most compelling individual part of Madonna’s first US Top 5 hit isn’t in its more grandiose notes, but in the immediate synth-funk that hits in the song’s verses and especially its undeniable bridge, which almost sounds like something out of a Zapp & Roger song – minus the vocoder, of course. The thing that makes “Lucky Star” so undeniable is in that tension between Madonna’s nascent, but still world-conquering, ambitions and the compact, groove-driven music she sings over. It helps that Madonna’s vocal performance takes on her characteristic sincerity – even as she’s recasting nursery rhymes and stardust into tales of desire, it’s impossible to say that she doesn’t mean it fully.

Ramzi Awn on “Borderline” [8.23]

There aren’t many songs that propel an actual physical reaction, but “Borderline” is one of them. When I was young, much to my grandmother’s chagrin, I used to sneak my walkman out in the middle of the night and dance to it in my driveway. If my parents didn’t know I was gay before, they knew then. Yearning with innocence, the single succeeds in melding two melodies together with ease; never before has a synth line so indelibly made its mark on a pop song. For those who doubt Madonna’s voice, look no further than her opening belt. Subtle, yet strong, the song is a masterclass in songwriting. Though it may be upbeat, Madonna’s helpless vocal gives “Borderline” its conflict, suggesting that she really is going to lose her mind. After all, she is on the borderline?.

Kat Stevens on “Like a Virgin” [7.62]

What if you could go back and do it all again? I wonder how many of you reading this were satisfied, disappointed, terrified or merely relieved after your first time. Maybe, thanks to a large amount of tequila (hi dere), you can barely remember it? Or maybe it’s yet to come for you, in which case I hope this paragraph hasn’t put you off. I lost my virginity in the late nineties, in an alcopop-saturated world where Beavis & Butthead would make a cross-country pilgrimage in their desperation to score. Unfortunately I absorbed that American Pie ethos, treating sex as just another milestone to brag about. First snog, first hand job, first shag: the Spark Purity Test gamification of sexuality! Ticked that one off the list, what’s next? At those crucial points, the How – and the Who – were almost irrelevant (sorry Ross), as was anything that came afterwards. Broken the seal, no big deal, right?

Arriving at university, I made this blasé laddette attitude part of my shiny new identity, as far removed from my school swottishness as possible. In reality it was a thin veneer of sex-positive confidence hiding a clumsy, approval-seeking naivety, snogging anyone who seemed even vaguely up for it, and unashamedly belting out “Like A Virgin” at karaoke, hoping no-one would notice that I was copying my schtick from Dorien in that episode of Birds of a Feather. “Like A Virgin” is about another fresh start, reminding us that the first time isn’t the be-all and end-all (thank fuck!), and that like any sport, sex becomes more fun with practice. A joyous rush of hormones and laughter with someone who’s in on the joke, it’s perfect for a supremely confident Madonna at age 26 (and indeed for the ageless Dorien), but just sounds ridiculous coming out of the gob of an 18-year-old fresher. Luckily for me, there’s no limit on fresh starts, each one shiny and new.

Jonathan Bogart on “Material Girl” [8.31]

The story of “Material Girl” begins in 1924, when precocious screenwriter Anita Loos began publishing excerpts of a fictional diary in Harper’s Bazaar. The idea wasn’t new – fictional diaries or letters full of contemporary slang and pseudo-illiteracy were one of the most versatile and popular literary forms of the period (just ask Ring Lardner) – but Loos’ protagonist, the blithely amoral and none too bright Hollywood gold-digger Lorelei Lee, was greeted as something new under the sun: a sexually liberated flapper unintentionally exposing the greed and hypocrisy at the center of 1920s high society. Collected into books, Gentlemen Prefer Blondes and its sequel, But Gentlemen Marry Brunettes, became enduring if minor classics of Jazz Age letters; the adaptation to tart Broadway musical in 1949, starring Carol Channing in her first lead role, one that would define her career (Hello, Dolly! used that performance history as subtext), and subsequently to sentimental Technicolor extravaganza in 1953, starring Marilyn Monroe in her own career-defining role (The Seven-Year Itch and Some Like It Hot were essentially Lorelei Lee fanfiction), was more or less a matter of course for such popular material. But the studio’s decision to loose Blondes from its period anchor in the 1920s (sensibly enough, as no one could accuse Monroe or Jane Russell of flapper silhouettes) freed it to take place in a never-never land that was pure Hollywood construct: the song “Diamonds Are a Girl’s Best Friend,” written for the 1949 musical, was memorably staged in pink, red, and black, all the better for the jewels (and Monroe’s platinum bob) to pop against.

Which is how we come, at last, to Madonna. She was in conversation with all this history, of course: part of her ongoing project has always been to raid the pop culture past for meaning that could be applied to the urgent dancepop of now. And so when she staged “Material Girl” as an explicit homage to “Diamonds” she was not only invoking Classic Hollywood but this whole involved history of comic but sympathetic portrayals of gold-digging set against show business. Typically, she complicates the issue by being vague about the meaning of “material” – does she mean it in the Gnostic sense of material vs. spiritual planes? the Marxist sense of dialectical materialism? the Sunday-sermon sense of accumulation of riches? All of the above? If we are, as seems undeniable regardless of sense, living in a material world, being a Material Girl may be unavoidable. Being made of flesh and blood, being a member of an exploited class, being someone whose value is defined either in terms of physical attributes or cash reserves — this is what it is to be a girl in the material world. She (Madonna, Marilyn, Carol, Anita) didn’t make this world, but by engaging it on its own terms, she can harness some of its power and cruelty for herself.

Jer Fairall on “Crazy For You” [7.38]

Madonna’s credentials as a balladeer had not exactly been proven by 1985. “Love Don’t Live Here Anymore”, the turgid break-up plaint from the previous year’s Like a Virgin, found her both overmatched and underserved; she had not yet learned how to work her way around anything without a strong pulse and at its core, and the song did nothing to play to her strengths (the retro-flavored “Shoo-Bee-Doo,” from the same album, feels like a more natural performance, but has been largely relegated to filler status, while “Love Don’t Live Here Anymore” warrants an inclusion on the 1995 ballads comp Something To Remember). That Warner had little hope for “Crazy for You”, consigned to the low stakes of the soundtrack to earnest high school sports drama Vision Quest, was no surprise. It was only after the film’s producers, Jon Peters and Peter Guber, sensing cross-marketing gold, pushed Warner’s music division to give it a shot on radio that “Crazy For You” was released as a single, a whole month after the soundtrack album had hit stores. It was a good move: the song not only became Madonna’s second US #1 single (after “Like a Virgin”), but it pointed the way towards the range she might now have felt confident to explore on later records.

Still, arguing that without “Crazy for You” there’d be no “Live to Tell” or “Oh Father,” no Bedtime Stories or Evita, however accurate, does a certain disservice to the song itself. Penned by veteran songwriters John Bettis and Jon Lind, “Crazy for You” represented a challenge for both its singer and producer, John “Jellybean” Benitez, taking both out of their dancefloor comfort zones, but it is one that they both met with such grace and precision that the results felt effortless: the sighing woodwinds and the echoey pitter-patter of the drum pattern stage a hazy slow-dance atmosphere that Madonna melts into with a vocal turn that is both as sweetly wistful as the most lovelorn of adolescent girl-group ballads and as achingly carnal as the most longing of adult torch songs. It’s pure, romantic bliss.

Alfred Soto on “Angel” [6.50]

One of the few early Madonna singles not killed by overplay and guess why: a wee little thing called “Into the Groove” thumped on its b-side. A sucker for her lower register, I get pleasure out of the liberty it allows her to underplay her sensuality and, in the case of “Angel,” let her co-star shine: Nile Rodgers’ pizzicato guitar, a more beguiling take on Western ideas about Asian music than his work on David Bowie’s “China Girl”. The sampled laugh stapled to the opening is the best in pop since Alison Moyet’s in Yaz’s “Situation”. John Lydon’s reaction to how Madonna and co-writer Stephen Bray appropriated “I can see it in your eyes!” from PiL’s “Swan Lake” has not been reported. Erotic heat as desperation – was it beyond him?

Katherine St Asaph on “Live to Tell” [8.69]

When True Blue was released, Madonna the singer had not fully become Madonna the Madonna, and “Live to Tell” had not become a set piece sung on a cross and attachable to whichever personal or humanitarian crisis she was performing that year. It was its own song, with its own mundane story: a commission for the Sean Penn vehicle At Close Range. Accounts vary as to whether Madonna wrote all the lyrics herself, or just changed a few, but almost all of them say she and composer Patrick Leonard intended a man to sing this. When I hear this kind of industry trivia, no matter how deflating, I usually believe it (because deflating’s usually how it works). But this story, I don’t believe. I can’t believe it. I cannot, in part, because “Live to Tell” is a song about lies, and the stories that replace them forever.

The instrumental, by Patrick Leonard – also of Leonard Cohen’s “You Want It Darker,” which isn’t much darker – is stark, practically unchanged from the demo. Tug the arrangement one way and it could be Peter Gabriel/Sade worldbeat. Tug it another and it could be that power ballad a man would have sung. (I tried mentally transplanting it into the 2000s, the first guy I thought of was Chad Kroeger, and I’m sorry, I can’t unhear it either.) The arrangement is of its time – the drum and synth tones should come with a complimentary bubble skirt, and a very ‘80s guitar sound seethes impotently in the background. But it’s also urgent as a shriek and elemental as a fairy tale, Madonna standing on a windy cliffside by the abyss, imperiled and alone. You don’t need the line “hope I live to tell” to discern the naked despair. (Male critics, understandably, fixated on the “naked” part; John Leland, in Spin, dismissed it as the work of a “cheap, tawdry voice” “vamping for the big-beat cocktail set.” A man can tell a thousand lies.)

“Live to Tell” is essentially a reversal of a confessional. “I have a tale to tell,” Madonna begins, priming the listener for a tale of sorrows – but that tale is never told, at least not explicitly. Here’s where that intent comes in. A man singing “a man can tell a thousand lies” can mean a thousand things, but a woman singing it can only mean one – shades, degrees, but only one. (The unavoidable is-it-context: True Blue was dedicated to then-husband Penn, later accused of gruesomely assaulting her. Penn denied the allegations, obviously; so did Madonna, decades later in legalese.) It’s no uplifting proto-#MeToo message song, though, but something bleaker and more real. Madonna’s worries are, in order, death, and aging past the point where anyone would care: “Will it grow cold, the secret that I hide? Will I grow old?” (At the last question, backing vocals swell like a scare chord.) Madonna’s a spectacular vocal interpreter; she clutches at “you can’t take that” like it’s her last friend, and every time the arrangement becomes calm, it’s punctured by one last held note in the chorus, a cry into nowhere. Until the end, that is: “You’ve kept it hidden well,” Madonna sings, the arrangement bestowing upon her a sweep of new chords like a congratulations medal. The key goes major, the synth melody resolves into some bullshit, the arrangement goes placid – in the demo, it drops out – and everything sounds well in the world.

Katherine St Asaph on “Papa Don’t Preach” [8.31]

What’s most striking about “Papa Don’t Preach” in 2018 is how workaday it is. Unlike most of True Blue, it wasn’t written by Madonna. The chorus is lifted wholesale from Sam Harris’ one un-wondrous hit “Sugar Don’t Bite.” The synth bass is a slightly more agitated version of the famous bassline to “Billie Jean.” The arrangement is Tin Man-stiff, or would be, if Madonna didn’t sing like she was prying it apart with her teeth. And the subject matter wasn’t as groundbreaking as some claim – apart from the aforementioned “Billie Jean,” the Lovelites got there in the girl-group era with “How Can I Tell My Mom and Dad,” and Whitney Houston would come out soon after with “Miracle.”

All these songs have one thing in common: namely, keeping the baby. With noted fucking idiot Anthony Kennedy’s resignation from the Supreme Court, the legality of abortion in the United States is once again under contention (the execution of abortion is not, was not and never will be), rekindling all the old flame wars to which “Papa Don’t Preach” was gasoline. Anyone who claims pop music and/or music writing has recently been ruined by social justice warriors and their Discourse is wrong, with a sense of memory that extends only as far back as his last Reddit visit. “[‘Papa Don’t Preach’ is] a message song that everyone is going to take the wrong way,” Madonna said upon its release. And take they did, take after take after hellfire-hot take. The ‘80s and ‘90s are full of fine vintage hand-waving freakoutery actually, what’s survived is fine vintage aggregation of hundreds of lost articles of vintage hand-waving freakoutery – about whether Madonna was pro-abortion, pro-teenage pregnancy, anti-abortion, anti-teenage pregnancy, pro-sex, anti-sex, sincere, trolling, Gone Too Far Now, and in which combination. Tipper Gore got involved, prompting at least one wag to come up with “Tipper Don’t Preach.” The Pope got involved. Ronald Reagan was made involved, by Madonna herself (“one papa who shouldn’t preach,” she told Rolling Stone) Proto-MRAs got involved; among the earliest takes was a dude bemoaning the girl “sponging off” her beau. Reservoir Dogs got involved, via the opening scene, where, amid some dick talk, Mr. Blue says he tuned out after “that Papa Don’t Preach phase.” (No, the “I don’t want politics in my music” thing isn’t remotely new either.)

These takes usually aren’t about any single song (or movie, or whatever) so much as the aggregate – the issue is never that this particular song doesn’t allow for abortion, but that none of them do. Still, as Tom Ewing wrote, there lurks “the temptation to look for a message in the song – the girl in ‘Papa Don’t Preach’ is keeping a baby, therefore Madonna thinks girls should keep babies. [There’s] the temptation to generalise – her decision is agonising, therefore this decision is always agonising.” The other temptation is to make songs out to be more subversive than they actually are: One Simple Trick to de-separate the art from the artist. “Papa” doesn’t quite support such an interpretation, but it doesn’t not. The lyrics – “but my friends keep telling me to give it up,” suggest that Papa is very far down the list of people whose input she’s sought. That input largely consists of ordering him what to do – “please be strong” (the audacity, that he’s the weak one), “I don’t need maybe,” “you’ll give us your blessing right now,” the very title. And most importantly, Madonna sings like Papa doesn’t exist, let alone preach: Cooing and moaning at the ends of choruses like she thinks it’s “Like a Virgin,” desperately rasping with all her voice like she thinks it’s “Livin’ on a Prayer.”

Austin Brown on “Into the Groove” [8.38]

It’s a dare, basically – directed at the object of the song, a placeholder for the Puerto Rican man Madonna ostensibly wrote this song about as she gazed at him from her window, but just as much at the listener. “Into The Groove” drips with lilting winks and coy sexual energy, obsessed less with the value of pleasure itself than its potentiality, and music’s power to assist in erotic curiosity. Madonna’s matter-of-fact introductory statement (“You can dance for inspiration. Come on – I’m waiting”) and its accompanying peppy, minimal synth pattern is immediately interlocked with a rippling bassline that tears open the track, a statement of intent in miniature that Madonna songs often specialize in. It earns the filmic introduction nearly immediately: more than any track she’d released to this point, “Into The Groove” is a synthetic mirror ball, a showcase for her everywoman disco diva contradiction, vocally and lyrically. Pinched high notes and cavalier, ping-ponging rhythms in her voice belie the slight interiorities of the lyric, but they inevitably come to the surface, as in, most prominently, the reverent tonal change during the bridge that would eventually blossom into “Like A Prayer” and Madonna’s later piety. “Only when I’m dancing can I feel this free” is the all-time Instagram caption of a bar, but it’s the following line that blows the whole thing wide open: “at night, I lock the doors, where no one else can see,” slightly syncopated and intoned with just a little bit of (perhaps performatively) shy self-awareness. The aforementioned potential – of getting outside yourself, of getting inside someone else (or getting them inside you, as the case may be), and of losing the outside world in the process of both – is a time-honored tradition in dance music, as well as songs about dance music, and here Madonna pares it down to bare essentials. In doing so, it exposes the crucial irony of dares: a lot of times, they’re as much about the one daring as the one being dared.

Edward Okulicz on “Open Your Heart” [8.33]

“Ah watch out!” she warns at the start, setting a scene for a romantic comedy playing out in just four minutes, and even though there’s no actual resolution in the lyrics, it’s difficult to imagine that Madonna doesn’t get what she wants at the end of it. “Open Your Heart” is a topic of well-worn lyrical desperation – unrequited love – and Madonna doesn’t just recast it, her voice seems to ignore the text and delivers it instead with terrifying triumph. That’s the centerpiece of its appeal; the odds are hopeless, but Madonna will win, the guy will win because he gets Madonna, and you will win. You can’t emulate that level of confidence, which is why Britney Spears only mimed to it in Crossroads.

Given to her as a rock track, Madonna made changes to the composition and production and every choice made is befitting of the biggest star in the world. It’s a perfect sounding record. The drums snap like clicks of fingers demanding a lover (or a servant) come at once to deliver her love, her drink, her happiness. The canned blasts of synthesiser that do what a blast of horns might do and aerobicise the track, perfect for running to. And Madonna will run the object of her affection over if she can’t chase him down. Stuck between her early helium voice and the more mature one that shone on ballads in the ‘90s, Madonna stretches, trying to find voluptuous corners of her voice that she would master later, and in the video she’s wearing outfits that more or less force you to take in her breasts. It’s one of her most relentless hits, but it’s also one of her warmest. And no wonder it’s Britney’s favourite.

Claire Biddles on “Like a Prayer” [9.54]

Like a mortal attempting to capture an image of God, it’s difficult to write about “Like a Prayer.” How to adequately surmise a song whose pleasures and mysteries are as wide and deep as the scripture that it alludes to? Every moment, every line feels a hundred feet tall. How long was the Virgin Mary in labour for? Madonna wrote “Like a Prayer” in three hours. It’s almost six minutes long but it’s never enough; running on never-ending cycles of tautness and release, melodrama and relief, that never fully resolve — fading out and pulling away from our grasp before we can fully comprehend it. I suppose there’s technical, musicological explanations for its supernatural wonders, but I don’t want to know them. I want to keep “Like a Prayer” where it has always been: just out of reach.

Scott Mildenhall on “Dear Jessie” [6.20]

You don’t need any more than the opening line of temporal parental anxiety to know that “Dear Jessie” is not really for children. It’s not a lullaby, but a song about singing a lullaby and the apparent terror that one day your child will wake up and no longer need you. They can and will get old, as will you, and so arises this: a phantasmagoria so elaborate that the reverie is clearly all its creator’s. It’s more idealised parenthood than idealised childhood, eliciting laughter rather than laughing, and yet that deep unease still occasionally reaches the surface – “never forget what I’ve said!”. “Dear Jessie” isn’t sugar-coated, but sugar-buttressed. These are ramparts of sugar, fantasies built for the protection of fantasies; fantasies of protection. And listening to a denial so lush, so sincere and so comforting, it’s hard not to feel protected.

Thomas Inskeep on “Vogue” [8.77]

You know “Vogue.” We all know “Vogue.” It’s an actual classic, almost 30 years since its release; it’s one of the Madonna singles that the world will most remember her by after she’s gone. Shep Pettibone used Madonna as his trojan horse to shove deep house (that piano line!) not only into the charts all over the world, but to the top of most of them. He crafted a perfect track, using stabs and samples taken from the Salsoul Orchestra’s “Ooh I Love It” with surgical precision. (And who did a 12” version of said record in 1982? Mr. Pettibone, that’s who.) Madonna, meanwhile, used his track to bring the world to the ball, to learn the wonders of voguing, to which she was introduced by her dancers Jose and Luis, of the legendary House of Xtravaganza. (BTW, if you’ve never seen the documentary Paris Is Burning, please do so. That will school you nicely, and more in-depth than Madonna could do in 4 minutes, on voguing and ball culture.) The song’s David Fincher-directed video is veritable high art, all B&W vintage Hollywood glamour. “Vogue” detonated like a bomb worldwide, and is still one of Madonna’s biggest global smashes, in a career made of them. It never gets old. It never gets tired. “Vogue” is eternal. “Vogue” is forever. “Vogue” is perfection. “Vogue” is life.

Matias Taylor on “Justify My Love” [6.83]

When it was released in 1990, the music video for “Justify My Love”, the jump-off single from Madonna’s era-defining The Immaculate Collection, faced such controversy that MTV banned it despite her being one of the network’s biggest stars. The clip is a voyeuristic, surreal trip into a seductive hotel space where Madonna playfully engages in sexual moments with both men and women – practically unheard of for a major celebrity at the time. The aesthetic is informed by a despairing, sophisticated sexuality influenced by European art house directors, marking a departure from the brightly-lit, upbeat visuals of her ‘80s period. The video, as striking as it is, would be nothing without the song – one of the most adventurous records Madonna had made up to that point. A Public Enemy-sampled trip-hop beat and ghostly synth lines perfectly balance each other, complimented by the subtle chorus hook that jumps out as the only piece of vocal melody on the track (apart from Lenny Kravitz’s backing hums).

“Justify My Love” is also noteworthy for debuting the spoken word style that would dominate Madonna’s next album, Erotica, and it’s not hard to see why she returned to it: her voice is dripping in sex, luxuriating in each syllable and perfectly encapsulating the unbridled lust oozing from the track. It helps that what she’s saying is as arresting as the sounds behind it: the lyrics play with notions of submission and dominance when it comes to unrequited love, demanding it (“love me, that’s right, love me”) while also acknowledging her powerlessness in the situation (“wanting, needing, waiting”), where she depends entirely upon the object of her affection’s willingness to reciprocate. In doing this, “Justify My Love” transcends mere A-grade porn groove jam status and becomes something much more nuanced; it’s about how to reconcile being an independent, powerful, self-affirming individual with the need for love and affection from another person. Do you give power to someone else over your happiness by letting them into your life (or bedroom)? Madonna would continue to explore this question through the years to come, but this track is perhaps the best example of her marriage between poetic sensibility and primal musical instincts in pursuit of an answer.

Jonathan Bradley on “This Used To Be My Playground” [5.91]

An accident of release schedules meant that I heard about Madonna long before I heard her. Pop music first captured my attention sometime after “Vogue” had captured the #1 spot in Australia, and many other nations besides. But whether she had new music in the charts or not, Madonna loomed over the mass culture in the early 1990s, even as it was experienced by seven-year-olds who had never heard her songs. She was an icon of celebrity, of sexual and spiritual transgression, of artistry and adulthood, and that I had not encountered her in any of these spheres only served to make her notoriety more inexplicable and more intriguing.

“This Used to Be My Playground” was the first Madonna song I heard, and I think fondly of it for that reason, and even more so because it was so uncharacteristic of what Madonna represented in mass culture; if anything, when I heard Madonna, the experience made her more inexplicable to me. But “Playground” is a beautiful tune: about memory and loss and the passage of time, generous in its production, with Madonna delivering her reminiscences in stately and controlled tones because the song is capable of filling the rest out on its own. To a child, it is legible too; children know playgrounds well, are familiar with regret, and are conversant in the fairytale genre, to which “Playground” lays claim. Probably the best thing about it is the dark intrigue in the byways of its arrangement, the little spaces of unreality reserved for the liminal spaces claimed by storybooks and, um, baseball movies. That posits it as a dark counterpart to “Dear Jessie,” another of Madonna’s most uncharacteristically delightful singles. After “Playground,” I would soon hear The Immaculate Collection and all her radio hits, and then those yet to come, and I would welcome them for the extraordinary innovation and vibrancy they brought to pop music. But I love “This Used to Be My Playground” because in it I learned who Madonna was, even when she was not who we thought Madonna was supposed to be.

Jonathan Bogart on “Erotica” [6.91]

I cannot tell you how unholy, how forbidden, how salt-and-iron taste and every nerve inflamed with urgency and dread this song sounded in late 1992, all the more so because I only dared listen to the radio in secret, behind closed doors, on plastic headphones with scratchy foam covers over the earpieces, all the more so because the music I acknowledged listening to was the cassettes of people in mullets who put “ministry” on their tax returns and praised God with gated drums and synthetic strings. Shep Pettibone’s dry, jangling beat, with its clipped, unnatural syncopation and the trebly hiss of tambourine shake, was like a Black Mass, a decadent perversion of sounds all 14 of my years had taught me to consider sacred. And Madonna’s throaty, largely spoken performance was both seduction and sneer: I understood instinctively, with a kind of grateful despair, that she was not speaking to me, that I was beneath her notice, irrelevant to her concern, only listening in on the inexplicable conversation of a far superior being. I believe I prayed for her soul, as I certainly prayed for mine when this came on on the radio and I found myself unable to turn away, stomach-sick, until the last bitter, beautiful crackle. All of which is comedy now, as silly and self-important as rhyming “hit you like a truck” with “teach you how to [sampled moans]”. Today “Erotica” sounds a touch juvenile, more camp than pornography, and I imagine that, for adults, it probably always did. Madonna’s exploration of sexuality that only ventured so far beyond vanilla was no doubt extremely meaningful for her as a purging of Catholic insecurities, and for the portion of her audience themselves on the cusp of adult sexuality; for me it was a gentle torment, like the Anaïs Nin volumes, smutty comics, and nude statuary I encountered around the same time. Eventually, however, the Internet happened, and I grew up.

Leonel Manzanares on “Deeper and Deeper” [8.36]

Dance music, especially the forms of dance music that were slowly becoming mainstream during the 90’s, felt like a cathedral; huge, cavernous, overwhelming. Like cathedrals, they were home to a communal spiritual experience: taking the dance floor is exactly the same as going to mass for so many of us. That big sound is characteristic of inescapable party-starters like Haddaway’s “What is Love” and other Top 40 hits that were part of the Euro-dance trend that gave us countless one-hit wonders, but it was artists like Madonna that solidified this sound as a pop force. Madge was no stranger to the NYC house scene, these elements have been a part of her sound for a while now, but “Deeper and Deeper” is where she has finally found the perfect balance between dance music exuberance and pop perfection. From that beautiful string section, to the flamenco guitar bridge, to that almighty house piano, “Deeper and Deeper” is a brilliant summation of her musical direction in the early 90’s, a period where she went from mere chart powerhouse to era-defining icon. This is also the peak of what I call “Imperial Madonna”; she has always taken elements from the underground and incorporated them into her sound and aesthetic, but the Erotica record – along with her Sex book – cemented her as a cultural figure that dictated which movements were truly relevant.

Alfred Soto on “Bad Girl” [6.50]

Imagining post-Evita Voice Lessons Madonna singing and writing “Bad Girl” is like imagining Donald Trump embracing right to work laws. Off-key, struggling to grasp the melodic and tonal shifts, Madonna says farewell to the let’s-try-anything spirit characteristic of her work in her first decade. Shep Pettibone and Anthony Shimkin’s block chord synths and light dusting of beats provide the mournful backdrop for the performer’s Method acting. Drunk by six, kissing someone else’s lips, smoking too many cigarettes, this character can’t stop the cycle of self-abasement – a side of Erotica that got lost amid the manufactured outrages over the Sex book. By peaking at a miserable #36, “Bad Girl” broke her streak of consecutive Top 20 entries. No wonder Team Madonna, panicking, released “Rain” as a follow-up.

Edward Okulicz on “You’ll See” [7.00]

Madonna retconned this as a sequel to “Take a Bow” in the video, and the two songs can be read as parts of the same story, but “You’ll See” is far more a theatre-destroying climax than a curtain-closer. If Madonna was in her musical phase, this one’s actual music would insist that it come two thirds of the way in, a few songs beforehand. Recorded for her collection Something To Remember, which places some of her best ballads into a new context, “You’ll See” is one of her lushest, but most broken songs. You can instantly hear what drew Susan Boyle and Shirley Bassey to the song to the extent that they wanted to cover it: it’s a song of strength in the face of the adversity of a person who with indifference as much as cruelty tried to break her. It’s a great song, and even more so if you can get past the aural equivalent of scenery chewing – Madonna’s performance is a little hammy at times, particularly on the final verse. Yet for all its lack of subtlety, I think it’s a dramatic and intense reading, projecting numbness, then defiance and anger, then uncertainty as the song fades out. And on paper these are some of her best lyrics. The way she uses the title (just two words) to flip other lines on their head (“you think that you’ve destroyed my faith in love… you’ll see”) and wrench the knife out of the song’s subjects hands and into their gut is tremendous. She’s already cried and admitted defeat, but “You’ll See” finds Madonna in a position where she can’t even speak fondly of the person who cut her, so she’ll sing as if hoping to dance on his grave. But anger, too, is defeat, and “You’ll See” ends as if she’s realised that herself for the first time.

Rachel Bowles on “Frozen” [8.09]

I remember seeing the “Frozen” video at #1 on Top of the Pops – a formative show for many of us of a certain age in the UK, and pretty much the only prime time space on terrestrial TV for Top 40 videos and artists lip synching to a studio audience. I was a very anxious child, and the gothic alterity of “Frozen” (however problematic now) and its sonic despair resonated deeply with me. Madonna hitting the arid ground – I attributed this to global warming, like I said, I was a very anxious child – and turning into a murder of crows, those drums signalling her siren song, one I knew in the pit of my stomach her lover would not, could not answer.

Iain Mew on “Frozen” [8.09]

Some songs change everything, and in doing so fix the moment of hearing them in memory forever. In 1998 I had almost no contact with new music and didn’t even watch Top of the Pops, but I remember the wall-mounted radio in an Italian hotel where I first heard “Frozen” playing through a slight layer of fuzz. I don’t remember anything about the station, even whether it was in English or Italian, but I remember that was where the song demanded my attention and wouldn’t let go. It did that much of that through unusual stillness, correctly trusting that what it was doing deserved the respect of quiet in response, though anything where the tension bursts in such shocking rattles of drums isn’t just about quiet. Similarly, Madonna’s performance is at one level that of a prophet here to pass on deep wisdom with detached, resounding authority, but that’s both true and not the full story, not complete without the sad resignation that it’s masking.

I heard “Frozen” in the same way several times that trip and had never heard anything like it. Having my world changed by something which was also of the moment felt subtly different and more exciting than even the most enchanting songs on oldies radio. When I started chasing that feeling more (and more and more) a couple of years later, I looked to the now with a convert’s zeal, and was put off by the Madonna of Music besides, so I never actually went back to where it started. Listening to “Frozen” now is an experience of not just revisiting memory and realising how much of the song itself remained fixed in my mind, but also realising how much of what I fell for hard in its wake – Björk’s vespertine encounters in the snow, All Saints taking the same William Orbit synth bubbles to the beach, the mystical humming drone of Radiohead’s “Pyramid Song” – was seeking not just the same feeling, but the exact same thing.

Lauren Gilbert on “Ray of Light” [8.38]

Wonder is an underappreciated emotion in pop music. Which seems odd to write out: we’ve all read the exact same interview from a hundred different artists, about how they are #LivingTheirBestLife and how it is so “wonderful” to be able to share their art with others. But songs about wonder are few and far between; there is little room in Top 40 radio for joy undercut with the knowledge that all joy must end, for a wonder that comes with a sense of one’s own insignificance. “Ray of Light” is an exception; it is awe-some, in the original sense – designed to provoke awe. Madonna is above raging against the dying of the light; instead, she dances off the fear of death. “Ray of Light” transmutes the terrible indifference of the world into a swirl of color, an excuse to move your body while you still have one. I find it difficult to even write about the nameless swelling feelings it provokes, joy-hope-fear, all at once; dazzling in every sense. That is: 20 years after it was first released, “Ray of Light” still sounds like the future, both terrifying and wondrous.

Austin Brown on “Drowned World/Substitute for Love” [6.67]

Ray of Light is sure to endure as the strangest entry in Madonna’s catalog, because it trades so explicitly in autobiography and the inhabitation of authenticity, when previously her entire career was based on the validation and justification of posturing as a method of self-creation. The William Orbit-helmed production is deliberately ascetic, nabbing little bits of jungle, arpeggiated guitar and ambient synth pads, then throwing in massive amounts of empty space. Madonna’s voice, honed from a few years in the Celine Dion Torch Ballad School Of Music, is no longer nearly as punkish as during her peak ‘80s period, but the syncopation in the song allows her latent desire to bubble up to the surface again in a way that it hadn’t for much of the ‘90s. And then there’s the lyric – a mission statement for a piece of AOR, rather than the miniature intros she favored for so many of her hits.

“Drowned World/Substitute For Love” was never a US hit, and it definitely wasn’t the first song audiences heard from Ray of Light. But its loping, portentous ambience sets the stage for Madonna’s “maturity” (although you could probably more accurately just call it her volcel phase) and justifies her Kabbalistic interests with the vigor a song cycle like Ray of Light deserves. Of course it’s no more “mature” than any of the songs on Erotica were. But it serves as a reminder that there’s just as much power in a secret, holy desire as there is in the secularized creation of a self.

Maxwell Cavaseno on “Think of Me” [6.09] and “The Power of Goodbye” [7.00]

At the core of every relationship is the mutual understanding that there is you and there is an outside force. No matter the title placed upon these connections, we all seek to navigate relationships with some sort of resolution from our exchanges; ultimately every blow or play or gesture or move has echoes in violence or softness on an opposing plane and we spend our lives being so very tactical even when we’re needlessly lacking of consideration. Madonna’s marked aggression and intensity manages to make every scenario feel close to conflict. When she sings about romance, there’s a consistent desire to penetrate, explore, and dominate. Ever the Leo, she discusses her lovers, their money, their sexualities and beyond with the eagerness of a predator. If she could fit it into a Top 40 pop song, Madge would’ve beaten every rapper to the “Blow your brains out/So I see what you’re thinking about” cliche because overcoming defenses and penetration lingers along through her constantly.

In ‘83 it’s there in the cheeky synth surges of “Think of Me”, where it’s playful and potentially bratty in how her subject has the nerve to fail to regard her as the utmost important thing. In ‘98 it remains, but downright militarized for “The Power of Goodbye”. There it’s very much the esoteric, witch-like Madonna of the millennial shift, projecting herself into ramparts and ciphers after discovering emotional intimacy with people who would become casualties or torturers in the following decade and a half… and yet still, the same Madonna we’d experienced before. What started off jabbing in needling need, smartly strutting across the brightly barbed synths of Reggie Lucas would widen and distend into showering omnivorous sorrow shackled to the gloomy wine mom trip-hop of William Orbit and Patrick Leonard to both haunt and elude all at once. Yet in each case a ravenous black hole feeling of desire that no matter how it evolves and matures, seems insatiable on the outside.

In 2018, that same Madonna is often the butt of jokes for having aged in a way that refuses to cease that eager, voracious demand for attention that was so often mistaken for “whoring” by those repulsed or dismayed by how unbecoming it can be to those finding themselves as spectators or even opposition by nature. When it finally ends, the conflicts put to bed in the absence of competitor, there will be no victor or resolution. Just a void where one of the most marked presences in pop did its best to demand its place in our hearts and minds, one way or another.

Leonel Manzanares on “Nothing Really Matters” [7.30]

For me, Madonna’s Ray of Light record will always stand out among her body of work, but the reasons why have changed as the years go by. When I discovered it, I was enamoured by that incredible sound: no pop record I had heard up to that point sat that comfortably along the rest of my mostly goth and metal-based record collection. The William Orbit/Marius de Vries production puzzled my senses: It was dark but somehow inspired a sense of hope. It came from the desolate landscapes of industrial music and techno, but its pop songwriting gave it an organic feel. Most impressively, it perfectly encompassed the trends and movements of 90’s electronica, but “Ray of Light” has never once sounded dated to me. I later caught up with the rest of Madonna’s discography, and my perception of Ray of Light dramatically changed. It was no longer just the sound, but the vibe of it: the mindframe it was created from, and its intention to inspire in the listener a mood of introspection and healing.

“Nothing Really Matters” is not the best track on Ray of Light, but it’s THE most Ray of Light track. It made sense as a single because of that, but also because it’s the one song that says the right words, in the right tone, at the right time. It is dedicated to her daughter Lourdes, yet she speaks to all of us – reflecting on the passage of time, the need to atone. Most importantly, it talks about what some philosophers call “the eternal now“. She mentions her younger self; young, vibrant, a person who lived to the fullest, but with a selfishness that caused her to make all sorts of bad mistakes. She mentions the material world, the one she proudly sung about in her early career, and how the excessive attachment to it brought her nothing but pain. Madge is a mother now, and a much wiser version of her is here with us. And then that line comes:”Nothing takes the past away/like the future/Nothing makes the darkness go/like the light”. It’s true in Kabbalah, true in Zen Buddhism, true then and true now. Especially now, at a time when looking back objectively to our destructive past can be our only hope for actually starting to plan a better future, one where we can actually undo the products of our selfishness and materialism.

Vikram Joseph on “Beautiful Stranger” [7.55]

The glossy, bleary-eyed William Orbit production carbon-dates “Beautiful Stranger” to the dying years of the 20th century with painful accuracy. With retrospect, on such an unusually light-hearted song (which may, admittedly, be partly by association with Austin Powers gurning all over the video), it’s an odd fit. Orbit’s range was impressive, escalating the high drama of “Frozen”, turning “Ray of Light” into a warped, pulsating banger, and weaving stunning dreamscapes for All Saints, but “Beautiful Stranger”’s sinuous glide falls into a sort of purgatory between club and bedroom. Madonna sounds fairly indifferent and far from infatuated, and, while I’m all in favour of eclectic song structures, it suffers from the absence of an actual clear-cut chorus. It’s an interesting footnote to a distinct era of Madonna’s career, but not much more.

Anthony Easton on “Music” [6.85]

The first line of “Music” is processed so much, pushed through a machine, made to sound genderless. The chirp after the line, going into a kind of vocalizer, doubles down on the artifice. The song then slides into something resembling Madonna’s voice. Not that the first couple of lines weren’t her voice – it kind of proves what might be an obvious point: that Madonna’s voice is one that is revealed through a constant set of artificial constructions. It is not something that is, but something that is done to. It is not blank, though. You can recognise a Madonna vocal even on the most processed or present production, even perhaps more so. Madonna has to fight. The value of her best work is when her aesthetic choices push against the aesthetic choices of a producer. The mutually assured agreement towards fashion is key.

However, it cannot be really fashionable. This push against a pop avant, or a technological avant, this mutual combat, slices ideas thinly enough that they can be sluiced through the market (for market here read American). So, Mirwais spent 20 years or so running through the edge of this bad taste, pan-European (and Afghan!) cheesed up Disco Punk. Not quite avant, but he kept up with tech, and he kept up with taste. He sent an album to Madonna, and the legend is that she was worried it was too rave. Those were the words that were used too – rave.

Here’s the weird thing, though. Every other Madonna dance track (before Ray of Light) could be conceivable fucked to, and danced to, and listened to on the radio, and they were perfect pop forever. The weird isolating edge of Ray of Light, no matter how genius it was, kind of gave up sex for a miasma of new wave spirituality. It was a new record, and a strange one, one that kind of split her career.

So, “Music” seems like an attempt to use Mirwais’ strangeness, and Madonna’s Ray of Light optimism, and her history as the ultimate populist, to make this great meta track; a kind of career summing up. It kind of doesn’t work – the lyrics are absurd, the line about the bourgeoisie almost scuppers the whole thing. Madonna is one of the great songwriters of the last 25 years, making tight stories out of small, perhaps common thoughts. She doesn’t do lofty as much as she does intimate – she is better at nostalgia, or one person talking to another person, than she is at soundbites. The production sounds awkward, it never quite completes an idea, and it never quite knows what to do with beats that are squishy or squeaky. She pushes against the production, but there isn’t anything that synthesizes after the combat. It is also kind of stagnant, and perhaps the first thing she did that now sounds dated.

I was also thinking that she doesn’t quite commit to the vocal fuckery – like she did in “Ray of Light”, or like Cher did in “Believe”. Here is the magic of the song – all of that said, it maybe is the first place where she shows a certain amount of anxiety. This song is a failure, but it is a failure where she is positioning herself, making statements, sorting out what she wants to do, and maybe for the first time, justifying her life. The whole album is like that, but that the song doesn’t succeed in the doing.

There is something haunting to that.

Claire Biddles on “Don’t Tell Me” [8.00]

Music was my first proper Madonna album. I’d been aware of her as a young child (who in the ‘90s wasn’t?) but hadn’t paid too much attention. I became instantly and overwhelming obsessed when a friend from school gifted me a pirated version of Ray of Light in early 1999, after all the videos and singles had already been absorbed into the culture. I saved up for three weeks and bought The Immaculate Collection and (with hindsight, perhaps inappropriately for an 11 year old) a huge poster of the cover of Erotica. I stole my mum’s copy of the Evita soundtrack, belting out “Don’t Cry For Me Argentina” in my room every night with the curtains open. When I wasn’t performing for an imagined adoring audience, I was fantasising about the point – surely not so far in the future! – when the best pop star and person of all time would release an album that was just for me – that I could analyse and pore over in real time, instead of this retrospective obsession.

When Music came out, I listened to it so frequently that I had to buy a replacement copy within three months. My nightly performances as Eva Perón were replaced by multiple run-throughs of Music’s ten weirdo dance-pop tracks. “Don’t Tell Me” became my favourite, maybe because it was easier to imitate during my regular after-school recitals than some of the stranger songs on the record, whose politics of gender and sexuality went over my head at the time.

Soon after the album was released, Madonna announced a four night residency at Brixton Academy, and my mum took a day off work to phone and try to get me a ticket. I cried for hours when I found out she had been unsuccessful, and internalised this trauma to the extent that I eventually stopped listening to Music after the concerts happened, too distraught to comprehend that these songs – my songs – were being performed to people who surely couldn’t understand them like I did. I only revisited Music again to write this blurb, and – listening with the context of the rest of her work – it strikes me how much “Don’t Tell Me” feels like a version of a song that Madonna has been making throughout her career: the don’t-fuck-with-me,I-don’t-want-to-hear-I-don’t-want-to-know, Extremely Leo Energy song that pops up every ten years or so as a warning shot. Deceptively light and simple, but with a firm hand. As a self-doubting Virgo who could always do with a dose of Leo energy, it’s been a good periodic reminder to be self-assured since I was a kid, even if it was unconscious at first.

Will Adams on “What It Feels Like For A Girl” [6.50]

The crux of the opening monologue, sampled from Charlotte Gainsbourg in The Cement Garden, is thus: “Because you think thatbeing a girl is degrading.” It’s devastating because we still see this attitude years after the fact, even in our pop music, from the ending scene of the “Stupid Girls” video to “Trust Fund Baby”: girliness is wrong. While this frustration is certainly reflected in the gorgeous, downtempo original by Guy Sigsworth, the remix by Above & Beyond is a complete 180, turning it into an uplifting trance anthem. Stripped of its verses, the song becomes a lonely plea hanging on to every word –for a girl, in this world – that’s bookended by Gainsbourg’s thesis.

It’s the perfect soundtrack for the video, a night drive through city streets that, true to trance music, is more wistful than empowered. This was the third Madonna video that MTV banned, for its violent content. In a sense, I can see why; there are flashes of edginess that don’t hold up – the “Pussy” “Cat” license plates, “Ol Kuntz Guest Home,” the 666 on the door – but really, the core of the video is the protagonist’s nihilism and utter disdain for the men of this universe: the bros leering at her at a stoplight, the dumbfounded cops, the street hockey jocks, the tough guy with a hot car. The final minute is the culmination – the uplifting harmony is gone, and we’re left with the strobing synths, spiraling over that singular line until it becomes dizzy. What we’re left with, as the slo-mo car crash unfurls, is catharsis that still resonates today.

Jonathan Bradley on “Die Another Day” [6.75]

“Die Another Day” is not a beloved Bond song; in some circles, it is quite a despised Bond song. It is not a beloved Madonna song either, included later on an inconsistent album awarded a far stonier reception than that received by its predecessor, Music, or its successor, Confessions on a Dancefloor. Those albums were pleasurable and sensuous, but American Life was harsh and unlovable; “Die Another Day” leaned into that quality.

A Bond theme is supposed to be theatrical and portentous, and though Madonna’s is, hers did not otherwise accede to the rules of the form; her contribution refuses classicism, bucking the Shirley Bassey conservatism demanded by an icon of masculinity on Her Majesty’s Secret Service, turning in instead a fiercely ugly composition. Austere string stabs are the closest concession the song makes to the decadent fanfares familiar to the film series, but on top of these are Madonna and Mirwais’ stretched and abused synthetics, sequences shorn and fractured and reconstituted. Madonna whispers and murmurs her lyrics, her voice electronically treated until it has been turned inhuman, while rhythmic duty is divided between pinging drum machines and the musique concrete intrusions of a misdirected tap dancer. “Die Another Day” wasn’t just a bigger explosion than any to be found in one of film’s most formulaically conservative institutions; it demonstrated that, into her third decade, Madonna could make music as unusual and as boundary-pushing as anything else she had produced in her career – or that existed in the contemporary pop world at large.

Dorian Jensen on “Me Against the Music” [4.91]

“Me Against the Music” is an oddity in both Britney and Madonna’s discographies – for starters, just by having both of them on it. Neither is a huge collaborator, and they almost never collaborate with other women who have similar starpower, despite their long careers. At the time the song was essentially unique, and the video definitely plays up its significance. Notably, it frames Madonna as in a position of definite power and Britney as a fruitless pursuer – a dynamic that was unmistakably shifting around this time.

As much as one could write about the video, I don’t want to lose sight of the fact that it’s also kind of a wild song. The vocals snap back and forth between these weird guttural gasps and something much more slithery and flirtatious, and the structure of the song stitches together a lot of very disparate elements. And of course there’s Madonna’s bridge, which feels airdropped in from a different song altogether, though it does feature the direct challenge (“If you think you’re so hot/better show me what you got”) that informs a lot of the video’s choices.

“Me Against the Music” isn’t a musical high point for either of its stars, but I think it’s worth talking about, if only for how monumental it was for Madonna and Britney to collaborate in the first place. It was brand new for them, and even now it is a major outlier in either’s body of work. “Let’s take on the song” indeed.

Scott Mildenhall on “Nothing Fails” [6.40]

Between the two opposing romantic clichés of star-written love and pure chance, only the latter feels in any way romantic. Adherence to a notion of fate and destined encounters negates all the lived experience, sensation – magic – from the way people make chance connections meaningful, even if the meaning they ascribe is one of being pre-ordained. You can have it either way –both ways if you like – but ultimately the power is in the people, and that includes the power to change minds on the matter, and to be struck with such strength for value systems to be shaken. “Nothing Fails” is the sound of that force being absorbed: giving oneself over in a way that may have seemed anathema to a new, delicate conviction of comfort, so strong and soft as to seem a surety of security; a quiet upending of perspective. Faith may hold power even if it comes easily, but far more startling is faith in faith’s absence.

Pedro João Santos on “Hung Up” [8.83]

I was four when I heard that clock ticking for the first time; the hectic rhythm of its hand coming in as a calling to something bigger than me. At that age, I wasn’t privy to all that a sound like that could encompass or the reinvention it symbolized in Madonna’s trajectory – I didn’t have a clear image of who Madonna was yet – or what figurative gates it would open for me. I couldn’t try to write about it, dissecting the music and words. Instinct conjured a primal reaction to a clock’s frantic noise. That feeling, which lingered far beyond late 2005, blossomed like a rapturous sense of fulfillment; a liminal state between fervent anxiety and electric rush, the belief of unearthing magic – as far as I can recall, that was the first time I felt music, not as passive listening, but art.

A disco-pop tour de force, “Hung Up” is a glittering landmark in pop music, breathing new life into the “Gimme! Gimme! Gimme!” arpeggios. It works because it’s proud and committed to its musical overtness, which enhances the subjacent drama and independence motif, but also subverts the musical extravaganza. The bridge evinces this, when the incrementally thumping bass swoops in to vanquish every sound, before becoming subsumed by the reappearing clock. For a brief interval, all that’s left is palpable tension; then, the ABBA sample returns to kick it into overdrive, while Madonna’s voice is solidified as confident and domineering.

“Hung Up” was my awakening as a pop fan, too – few things were as monumental in my pre-pubescent years than Madonna opening the EMAs, turning the largest arena in my country, Portugal, into a throbbing discothèque. But this song would progressively hold a deeper, personal meaning that I only start to grasp years later. My first manifestation of queerness might have come from a sudden impetus to imitate Madge’s studio choreography in the video every time it aired. It was my very own “Thriller”: I never cried at zombie Michael’s terrifying glance at the camera, but I would well up tortuously if I tuned in 4 minutes too late into VH1 and “Hung Up” was already ending. Whenever I got the chance to witness it, the song still held its power of revelation. I didn’t seek it out for a few years, but, just as rapidly as the beat first emerges in the track, it eventually resurfaced in all its glory. By then, a part of me that’s just as bold, bright and brave was already underway. I couldn’t keep on waiting.

Alex Clifton on “Hung Up” [8.83]

“Hung Up” wasn’t my first Madonna song – that was “Music”. Nor is it actually my favourite Madonna song – that’s probably “Like a Prayer”. But “Hung Up” was my Madonna song, one of the first that really spoke to me. I bought it on iTunes when I was 13 with my own money, which seemed like a huge investment at the time. I still remember the first time hearing it and something electric crackling within me. When you’re young, you love things so intensely that the rest of the world seems to fall away, and “Hung Up” did that for me. Everything from the ABBA sample to the iconic music video with the pink leotard to the “time goes by so slowly” hook sent me into a frenzy; any time I heard it played at a school dance, I felt like Madonna was personally coming through the speakers to sing to me. At 13, I had never experienced any kind of genuine heartbreak aside from two obsessive crushes, but that didn’t stop me from identifying from the speaker. I was so hung up on these boys! How could I be hung up on them when they never bothered to talk to me? No matter; I was done with them, and they’d only realize what they’d lost when they saw me strut away. In reality I was never that confident as a teenager, but Madonna made me feel like there was a version of myself that existed out there – maybe somewhere in the nebulous future – that would one day be powerful enough to walk away from anyone who played around with her. I’m still working my way there, if I’m completely honest, but I’ve got Madonna to guide me. Somehow that makes all the difference.

Jibril Yassin on “Sorry” [7.50]

On an album as maximal as Confessions on a Dance Floor, “Sorry” sounds ready to sink into itself, its vulnerable heart encased in layers and layers of ‘00s Eurodance ice. Every detail speaks of betrayal and resignation, the kind of resignation that comes creeping in after having been done wrong so many times by the same person or thing, underlined with the help of icy synth patches and strings. “Sorry” is supposed to tell us everything we need to know about striking it out on our own after we’ve been fucked over, but it’s not an uplifting call to arms or a dismissal rooted in casual joy like the best Madonna singles tend to be. Instead, what we get is a cool acceptance. At 47, this was the triumphant kiss-off Madonna was always gearing up to write. It feels earned, much like the best victories age tends to bring.

Jacob Kuppermann on “4 Minutes” [4.38]

“4 Minutes” is excessive even by the maximalist standards of the artists involved. The collaboration between late-imperial Madonna and peak TImberlake/Timbaland is a gaudy hammer through the skull, bludgeoning you with what is perhaps the world’s ugliest horn hook until you let the weird anti-chemistry of Madonna and Timberlake in. Everything sounds simultaneously sweaty and sterile – Madonna is clearly giving her all, but she and Timberlake sound like they recorded this on separate continents, with even the quick handoffs in the verse sounding forced. Yet “4 Minutes” works far more than it has any right to; the horns and clattering percussion form into something resembling a groove, and even at their coldest, the two vocalists are too charismatic to let an endearingly odd global-warming-activism-through-sex-talk lyrical conceit go to waste.

Will Adams on “Bitch I’m Madonna” [3.62]

This is not a good song.

Even leaving aside its extra-musical context, “Bitch I’m Madonna” is bad, a series of choices that lie somewhere between obnoxious and bewildering: 1) The strange vocal processing throughout that makes her sound like she’s singing through cotton. 2) The snare becoming considerably quieter in the last chorus for seemingly no reason. 3) Undermining Sophie’s presence – to Madonna’s credit, a collab that was ahead of its time – by upstaging her more interesting synthwork with Diplo’s sweaty trap buzz. 4) Reminding us at every turn that Nicki’s there via a sub-par catchphrase (“B-B-Bitch move”). 5) The “Lucky Star” reference, which would have been fine had it not already been done on “Give Me All Your Luvin’” three years prior. 6) The ending, an aural hell of a hundred rolls of packing tape sounding at once. Oh well. At least there’s a decent remix!

But “Bitch I’m Madonna” is interesting in how it relates to the critical narrative that has hounded her for most of this century – in effect, it is the apotheosis of her Medoner era. The received wisdom is that, no matter what, any endeavor is seen as “desperate,” “out of touch” or “tired.” And while this is certainly rooted in sexism, the video… doesn’t really refute this. It’s a kitchen-sink production filled with cameos – the most high-profile of which were seemingly filmed in some dark room backstage before the Great Tidal Summit of 2015 (was Deadmau5 unavailable?) – that is only interested in showing that… Madonna can rope in famous people for a quick video shoot, because bitch, she’s Madonna. The cameos and the oversaturated color and random makeouts and the party vibez are meant to be exciting or thought provoking or shocking… but they’re not. Nor is the song. The word “bitch” isn’t all that scandalous anymore, not after Britney made a single out of it two years before, and not after Cee-Lo was able to drop an actual F-bomb on the charts in 2010. But this is where we are. We’re living in a pop culture where we’re less fazed by this stuff, where visuals once banned by MTV – “Erotica”;“Justify My Love”; “What It Feels Like For a Girl” – barely merit any pearl-clutching today. So why hold Madonna to the standards of whatever modern-day transgression would look like when she’s been partially responsible for creating the very space where such transgression is possible, where female artists are allowed to push boundaries and break taboos and accumulate decades’ worth of Wikipedia “Controversy” subsections? She’s paid her dues – bitch, she’s Madonna.