Albums: Erotica (1992), GHV2 - Greatest Hits Volume 2 (2001), The Confessions Tour (2007), Celebration (2009)
Songwriters: Madonna/Shep Pettibone/Tony Shimkin
Producers: Madonna/Shep Pettibone
Contains samples of “Jungle Boogie” by Kool & the Gang, and “El Yom ‘Ulliqa ‘Ala Khashaba” by Fairuz

“In a sense, Erotica was the biggest one of her career. It was the one that moulded her, that gave her the access code to what she’s doin’ now. True Blue etc. - it was good to get those numbers out the way first… Set up the template for what you wanna do when you get older. Fifty million plus records under your belt, you’re good. If the label can’t support what you’re trying to do, fuck ‘em. On one level she’s asking, how much do y’all really believe in me now?”
“She was bringin’ it from her point of view as a woman, bringing it to the forefront for real. That set the template now, for your Christina Aguileras, Britneys, Beyoncés. She paved the road for a lot of that. You can be nice and clean and then a freak. And there’ll be a lot of money for you in the end!”
- Doug Wimbish of Living Colour, bassist on the Erotica album

The majority of Madonna’s music is, simply, inseparable from its imagery and the cultural context in which it was originally heard. And rightly so; the full extent of her artistry cannot be appreciated via listening alone. But for the last eighteen years, fans have been trying to hear the Erotica album without the backlash Madonna experienced around its release. Seeing it for what it really is, the music - and by extension, the imagery - has a depth that belies the public opinion. And yet, it’s stylistically scattered, Madonna’s aims not quite clear; perhaps all too appropriately for an album as vaguely named as Erotica.

Though the title track did surprisingly well, peaking at #3 on the Billboard charts, the Erotica album has sold a mere five million worldwide - just more than a fifth of True Blue’s sales. But with Madonna just about excising the sense of ’80s pop euphoria from her music, that was to be expected.

On the surface, Erotica’s hip-hop beats and alternately whispered/distant vocals sound like a continuation of Justify My Love. But where Justify My Love was sincere - Ingrid Chavez’s deepest fantasies set to music - Erotica is ironically devoid of the romance Madonna, or more accurately, Dita, supposedly invokes from the outset.

Though Madonna dictates the terms - “I’ll be your mistress tonight”, “if I’m in charge” - her soft intonating uses the power of suggestion gently, taking the reins as if for your benefit. In a way, it’s the same dominant role she always had in her relationship with her audience, but instead of the Blond Ambition era’s take-me-or-leave-me boldness, she pillow-talks the listener into loving her back.

Unlike Justify My Love’s stripped-bare feel, Erotica casts a smoky backdrop, with Kool & the Gang’s horns and the uncredited, vaguely Arabic vocal sample emerging intermittently from the haze. Even with only one hook, a chorus just explicit enough to make singing along in public awkward, it’s an appealing enough production that maybe, when they drove it to #3 on the Billboard charts, the public were merely buying into a pop song, not Madonna’s sugar-coated idea of sexual liberation.

More than any other Madonna song, Erotica is masquerade, encapsulating the Sex book’s occasional tongue-in-cheek tone without all its aspirations of being transgressive art. Gently seducing the world into accepting her ideals of sexual openness - perhaps her final sex-positive feminist act - was likely the best way to go about attempting to remove the taboo from sex. But unfortunately for her, the not-so-forward rest of the world found the idea considerably harder to swallow when exposed to actual nudity.

“Give it up, do as I say
Give it up and let me have my way
I’ll give you love, I’ll hit you like a truck
I’ll give you love, I’ll teach you how to…”

(browse the Sex book above, or view the individual pages, or just download it in high quality - because we all know you’re going to buy a copy one day… yeah, right.

Just out of curiosity, does anyone actually own one?!)

The Sex book.

Unlike just about everything else Madonna (except her acting career as a whole, successes and all), it hasn’t been reevaluated. The consensus seems to be not to consider it a misstep, nor to forgive and forget - merely to forget about it entirely. And though Madonna has never once expressed regret over the project, with the book long out of print, she may as well have disowned it. Here’s a typical after-the-fact quote:

“Well, I didn’t write a book about sex. I wrote a book that — I mean I published a book that basically was sort of a — an ironic tongue-in-cheek, sticking-my-tongue-out-at-society photo essay…”
“Yes, well it worked, obviously. It sold and people reacted to it.”
“It pissed off a lot of people, too… I think that there were a lot of people that were freaked out about it, yes. “
- Madonna with Larry King, on Larry King Live in 1999

All entirely true, and yet she gives no insight whatsoever into why she had to create the book. She’d evoked both irony and social commentary in the past without having to literally bare herself (much), nor to stretch her public reputation for boldness to its breaking point. That her nature was never to do anything by halves simply doesn’t explain why she went as far as she did. Was she really trying to change people’s views on sex, or just challenge them, inevitably offending the usual suspects whilst destroying her last shred of self-consciousness at the same time?

“And by the way, any similarity between characters and events depicted in this book and real persons and events is not only purely coincidental, it’s ridiculous. Nothing in this book is true. I made it all up.”

The book itself is… well, interesting. That a celebrity would bare themself for more complex reasons than publicity, titillating the opposite sex or showing off their physique is, perhaps, a shocking concept. Maybe, even after Justify My Love, it was still jarring to see Madonna looking glamourous as ever whilst dressed in leather S&M gear, or writing occasionally sophomoric tributes to masturbation or her vagina. But the images are more confrontationally blush-inducing than shocking - except maybe those of her cavorting with Vanilla Ice, a metaphor for life’s abject unfairness.

There’s no question that it’s an erotic art book, not so much pornography; each image feels as if it is presented as art with a purpose. It’s just not always clear what that is - Madonna vying for the attention of a gay man may be a fascinating image, but her in a Big Daddy Kane/Naomi Campbell sandwich may just be self-indulgent.

Not quite celebratory, not quite shocking, the Sex book wants to provoke a reaction, but really just is - an odd state of being for something so difficult to produce. Songs such as Like a Prayer and Vogue inspire a vast number of interpretations and associations - all of which feel entirely intentional on Madonna’s part. But Sex is more postmodern - devoid of a strong sense of intent, little else remains but the subjective interpretations it provokes, even amongst those who never even read it. Perception becomes reality.

Doctor: “Have you ever been mistaken for a prostitute?”
Dita: “Every time anyone reviews anything I do, I’m mistaken for a prostitute.”

And that’s exactly it - without the surrounding controversy, perhaps only the most dedicated of fans would have gotten anything out of the book. Instead, with all 1.5 million copies worldwide of the first edition sold out in three days, it quickly became the highest-selling coffee table book of all time. The merely curious bought something they would never quite appreciate; the apathetic grew entirely sick of her overexposure, beginning the backlash against her. Madonna did everything with an awareness of how her audience would react, but in selling a decidedly un-mainstream erotic art book to the world, what did she overestimate - the wider public’s tolerance, or her own power?

“You’re supposed to stay popular, and do things that are popular, that’s what the word means. Once you cross that line there’s a lot of fury to reckon with. I think that because everybody did buy the Sex book in spite of the fury it caused, people made up their minds that they weren’t going to be duped, and they punished me… I’m proud of the way I acted because it set a precedent and gave women the freedom to be expressive. I’m proud to be a pioneer.”

YouTube / AOL

Director: Fabien Baron

The Erotica video is more of the same, using footage from which many stills were taken for the Sex book itself. The concept is a little more powerful when visually brought to life - seeing Madonna dressed as Dita with the mask, single gold tooth and Freddy Krueger nails illustrates just how much of a character she was. Full of fleeting, grainy images, that overall sense of vagueness remains.

Perhaps the best ever version of Erotica was performed on the Confessions Tour; using lyrics from the original demo, it trades the erotic for a deep romantic longing, and is generally AMAZING.

Albums: The Immaculate Collection (1990), Celebration (2009)
Songwriters: Lenny Kravitz/Ingrid Chavez, additional lyrics by Madonna
Producers: Lenny Kravitz/André Betts

After eight years and eight Billboard number ones, tens of millions of records sold and, finally, undeniable critical acclaim with her most personal album yet… For a Madonna with no perceptible end to her creative or commercial peak in sight, where do you go? How better to demonstrate the potential for true, unreined artistry in the mainstream than to seductively whisper your way to number one?

But the fact that Justify My Love is also the highest-selling video single of all time reinforces the role of controversy in her work - largely to generate dialogue and keep her in the public consciousness, but also what her fans understate and her critics overemphasise: to sell records. And despite MTV’s banning of the Justify My Love video, the resulting debate over censorship and video single sales - the first of their kind - served to continue their symbiosis with Madonna in the long run.

In a way, Justify My Love is controversial for the wrong reasons. Each individual sound in the minimally produced song - the warm yet never-quite-resolving synth strings, the mind-bending drum loop, the generous reverb on Madonna and Lenny Kravitz’s backing vocals - is perfectly executed. The lyrics are poetic, sensual; possibly the most direct, genuine expression of desire Madonna ever put to record. But they weren’t exactly her expressions.

Our culture has matured beyond viewing popstars who don’t necessarily write all their own material as some sort of discrediting fact. Were the Beatles or Aretha Franklin in any way diminished as artists for including so many covers on their albums, or Thriller worse because Rod Temperton wrote it? Pop music is about interpretation through performance - as vital an aspect of artistry as anything else. But Justify My Love’s original writer never intended for Madonna to record it. Ingrid Chavez - a poet, Prince collaborator and actress (for a part Madonna rejected) in his widely panned film Graffiti Bridge, originally wrote it as a poem, recording the song in its initial form during a studio session with André Betts and then-lover Lenny Kravitz. In search of commercial interest, Kravitz wrote the chorus and other instrumentation, eventually bringing the song to Madonna of his own accord. Kravitz convinced Chavez to sign a document granting her no songwriting credit, with a mere 12.5% of publishing royalties for the song’s airplay - but at least invited her to the studio whilst the final mixes took place. She was stunned by the quality of Madonna’s vocals, stating:

Chavez sensed an unspoken awkwardness from Madonna, who may or may not have been fully aware of Chavez’s role in effectively ghostwriting the song. Her feelings lay dormant until after the song’s release when Prince, recognising her vocal style, warned of the copycat accusations that could arise upon the release of her own, similarly styled solo album. When a journalist finally confronted her directly, she admitted she wrote the song - the article sparking widespread condemnation of Madonna’s “wholesale thievery”. Chavez ended up suing only Lenny Kravitz, reaching an out-of-court settlement where she received credit and another 12.5% of disc royalties on subsequent pressings.

Kravitz had also, discovering the beat by picking the album up from a pile off the studio floor, sampled Public Enemy’s instrumental Security of the First World as the backbone for Justify My Love without credit - ironically, taking from a group who often sampled and reinterpreted dozens of uncredited songs on single tracks, turning sampling into an art form. Though their producer Hank Shocklee expressed vocal affront via the Young Black Teenagers’ answer record To My Donna, the lack of credit for the sample was generally accepted - or perhaps ignored, either in the face of its incredibly effective reappropriation, or due to the much further-reaching issue with Ingrid Chavez. The latter raises many questions - though the song itself is undeniably brilliant, does attempting to pass it off as belonging to someone else diminish our perceptions of the artist? Lenny Kravitz certainly appears to deserve the blame on both counts - yet he also deserves praise for the song’s production.

By suing Kravitz, what did Ingrid Chavez gain in the long run besides further royalties? In a world where the misconception that Madonna does not write her own songs still exists, how many casual listeners are even aware of songwriting credits? Taking that into consideration, Justify My Love is perhaps not so different from Like a Virgin - another song where Madonna skilfully adopted (some would say imitated, or stole), and likely surpassed the vocal style on the original demo. Madonna’s performance should not be underestimated - for example, compare her version to Vita and Ashanti’s cover for The Fast and the Furious soundtrack - in an act of extreme irony, Madonna denied permission to release a cover with Vita rapping her own original verses, allowing only the direct cover’s release. As a result, it fails completely at both interpretation and imitation - its stilted, read-aloud delivery over the exact same beat effectively renders it mediocre karaoke.

In the end, though Ingrid Chavez is entitled to feel betrayed, her lack of regret is the most mature response possible. No matter what it did to/for her, the song’s far greater exposure through Lenny Kravitz and Madonna was ultimately a victory for the art, if not the original artist. And we’re all a little bit more fortunate for it.

Producer: Phillipe Dupuis-Mendel
Director: Jean-Baptiste Mondino

The video takes place in the rather intimate setting of a hotel room, instead of the song’s sweeping “kiss you in Paris/hold your hand in Rome” visions. But on the other hand, where the song is an intimate exchange between lovers, the video shares Madonna and then-boyfriend Tony Ward’s oddly surreal experience with a number of androgynous, contorted figures - perhaps reflecting the very public context in which anything pop or celebrity-related, however personal, is viewed and dissected. The initially burned-out Madonna meets her lover in a hotel corridor, he submits, she takes control and delays his pleasure as the onlookers become participators… and rejuvenated by the end, the message is simple: sex (or at least Madonna’s idealised view of it) as an equalising force is empowering, rewarding, self-improvement. As always, Madonna lends weight to the marginalised - depicting elements of S&M in such an open, unselfconscious manner asserts that there’s nothing wrong with experimentation, going beyond the vanilla.

Where Madonna presented the sexual openness of her Erotica period as a borderline crusade, interwoven with a tongue-in-cheek irony not so decipherable to the mainstream, Justify My Love can more easily be taken and understood at face value. As a result, it is easily her clearest, most resonant message regarding sexuality. Feminism was never so seductive.

Infamously, MTV banned the video, more due to its suggestive themes than its very brief nudity - apparently they found “the whole tone” too threatening to even consider playing it late at night. Madonna’s impassioned appearance on Nightline to defend the video is essential viewing - it’s still inconceivable to imagine a popstar cutting through the record companies and press releases to make such a public, vocal statement. Though she acknowledges the resulting video single sales with a wink - “lucky me” - and though she deems MTV an “important marketing tool”, it’s entirely Madonna-as-artist, explaining that as the necessary visual expression of the song, the video was shot without concerns over censorship or an intention to sell it. With Nightline as a legitimising platform, she expresses two main concerns: firstly, and less overtly, that “businesswoman” is as much a compliment as an artistic dismissal. Her conviction and sincerity are convincing - though combined with, secondly, her agenda to promote public discussion of censorship, she elicits even more of a reaction from conservative detractors.

Without wishing to paraphrase excessively, she touches briefly on other important issues:

Madonna’s vision of the future… how telling. And yet, another 19 years later, in a victory for practicality, Justify My Love appears with breasts censored on her Celebration: The Video Collection DVD. I refuse to suggest there’s a single conclusion to be drawn here.

Albums: I’m Breathless - Music from and Inspired by the Film Dick Tracy (1990), The Immaculate Collection (1990), I’m Going to Tell You a Secret (2005), Celebration (2009)
Songwriters/producers: Madonna/Shep Pettibone

vogue /voʊg/
–noun
1. Popular acceptance or favour; popularity:

March 20, 1990: Madonna releases Vogue; until Hung Up tops the charts of over 45 countries in 2005, it is her most successful single worldwide.
April 12-August 5, 1990: Madonna embarks on her Blond Ambition World Tour, playing 57 shows in Japan, North America and Europe. Widely considered one of the most iconic tours of all time, its combination of religious and sexual imagery also courts controversy when the Pope calls for a boycott of her performances in Rome.
May 22, 1990: I’m Breathless - Music from and Inspired by the film Dick Tracy is released, featuring Madonna originals alongside songs by famed musical theater composer Stephen Sondheim. It sells over five million copies worldwide, and Sondheim wins an Academy Award for Best Original Song for Sooner or Later.
June 30, 1990: Dick Tracy finally hits cinemas after years in development. Warren Beatty directs, produces and stars as the titular character; Madonna has a supporting role as nightclub singer Breathless Mahoney. Despite mixed reviews, the film wins three Oscars between seven nominations, and is a commercial success.
November 13, 1990: The Immaculate Collection, Madonna’s first greatest hits compilation, is released. It goes on to become one of the highest-selling albums in history, with over 30 million copies sold worldwide.
May 10, 1991: Truth or Dare (known outside the U.S. as In Bed with Madonna), a film documenting Madonna’s Blond Ambition World Tour, is released, becoming the sixth-highest earning documentary of all time.

Vogue is, amongst many, many things, the sound of a woman on top of the world. But there’s no sense of arrival, no self-congratulatory platitudes; in fact, not one “I” in the entire song. No, what makes Vogue her crowning glory is that it is entirely empowering - both her most refined, universal “express yourself” call to her audience, and a true tribute to her predecessors, yesterday’s icons. Yet even without a single mention of Madonna herself, it’s still very much about her - for the true measure of her achievements in seven years of fame is that no one else could have convincingly written, sung or performed Vogue whilst coming off as even more of an icon than the Hollywood giants mentioned.

The embodiment of “pop” in every sense of the word, Vogue is also a celebration of the entire concept of popular culture and its power to move people, both literally and figuratively. For what is the greater art - an epic that touches a few people profoundly, or a brief, fleeting moment that reaches the entire world? Madonna would answer with disregard - having proven over and over that complex artistic statements and zeitgeist -level popularity can go hand in hand.

The cultural backdrop upon which Vogue (both song and dance) was built was not an especially happy time. The late ’80s was particularly devastating for many of Madonna’s most dedicated fans in the gay community, and the deaths of close friends, especially her dance teacher Christopher Flynn and artist Keith Haring, made AIDS a very personal tragedy. Her response was to include safe sex educational inserts with the Like a Prayer album, and to dedicate the first Blond Ambition date in New York to Haring’s memory, donating all proceeds to AIDS charities. But the most anyone could do to help would never have been enough.

Her artistic response, however, varied - though Spanish Eyes was a poignant, sympathetic prayer for the suffering, Vogue urges the listener not to dwell on it. LGBT magazine Advocate may have deemed “Madonna’s dance tracks… a necessary escape that was nearly transcendental during an era when our community was seeing more than its share of heartbreak and horror”, but while the archetypal modern depiction of dance may be that of clubbing in various levels of inebriation, dance to Madonna has never merely been about escapism. Stemming from her classical training, it represents first and foremost a form of self-improvement and artistic expression - confessions on a dance floor, not hedonistic partying. Madonna offers an empathy through dance, an emotional resolve that goes beyond mere escapist entertainment - leave that to other pop tarts. Great art exists to reflect upon, to empower the person experiencing it - and hence, Vogue cannot turn a blind eye to the suffering and hardships in life. If anything, they make the best of times even more glorious in contrast. She once sang “forget about the bad times” - but here, it’s “look around”. Don’t ignore them.

The utter perfection of Vogue’s title becomes even more apparent when considering its musical applications - though hardly the first house-influenced song to hit the mainstream, Shep Pettibone’s beats breathed new life into the drum machine after its omnipresence during the ’80s. Though that sound, itself a product of the trends of its time, imprinted itself irremovably on the pop of the next few years - heard everywhere from Saint Etienne to C + C Music Factory - the rest of Vogue is inimitably unique. Such minute-long, breathlessly anticipatory intros are virtually outlawed in pop - and with the out-of-nowhere rap and soaring final chorus, the song is peak after peak of the pure elation Madonna so consistently delivered in the ’80s. Vogue ushered in the ’90s with an unshakeable confidence that’s odd in hindsight, considering the fallout from the Erotica period that followed. But perhaps Madonna knew she’d by then taken dance-pop joy and her popularity to the limit. With her one musical consistency, the desire to never repeat herself, maybe it was best to close the first chapter of her career with a bang, and move on, whatever the cost.

2. Something in fashion, as at a particular time:

Having been originally written as a mere b-side to Keep It Together (but universally recognised by Warner executives as deserving more), Vogue is often cited as being out of place amongst Madonna’s Dick Tracy contributions on I’m Breathless. But as far removed as its house beats are from the authentically jazzy period pieces, their overall aims of glorifying pre-rock ‘n’roll-era imagery are similar. In fact, Dick Tracy is a film utterly obsessed with such style (perhaps to the detriment of its plot) - its unique visual presentation remains loyal to the original comics whilst at the same time being unlike anything else seen in cinema. Vogue aims for the same kind of retro; a tribute to the fashions of yesterday through a modern lens (courtesy of technological advances), with one major difference - Vogue doesn’t just imitate the 1930s. Revivalism without reinterpretation is inevitably inferior to the original - and Vogue was utterly current, a cultural high point of how retro should be done; not a recreation, but a celebration of the past.

It’s populist. Superficial. Style over substance. A passing fad. Talentless. Artless. It promotes sexual promiscuity and moral deviance amongst today’s easily influenced youth.

Those are all criticisms that’ve at one point been made of Madonna, pop music in general and many of the above stars. In such a context of cultural superiority complexes, Vogue becomes a statement of defiance, a defence of the mainstream as a delivery for the farthest-reaching, most broadly affecting of art. The rap effectively canonises the greats of Hollywood’s golden age; proof in hindsight that fame justified by talent sticks, and gross critical underestimations do not. Only (ironically) the most superficial could fail to draw parallels - for who else had the stardom, the cultural influence to have such a generous tribute serve as their own coronation? Such names hardly towered over Madonna as early as 1990, let alone twenty years later. On the other hand, Madonna is still too divisive a figure to (perhaps ever) be viewed so fondly by all of popular culture, but it’s just possible that - with Lauren Bacall sadly the only one still living - she has surpassed their fame. But that’s beside the point - with the immeasurable contributions of so many greats to the cultural iconography, everyone wins.

To have incredible style is to have substance. For that and much more, Vogue suggests that they will be remembered.

–verb
To dance by striking a series of rigid, stylized poses, evocative of fashion models during photograph shoots.

Director: David Fincher

Though Madonna had well and truly mastered the art of storytelling in the music video by Like a Prayer’s release, Vogue is just as compelling without one. Watch it 20 times and you’ll still notice new details, facial expressions, shots that last only a handful of frames - watch it 50 times and you still won’t be able to recreate the choreography. The visual performance is, of course, where the dance truly comes to life - and Madonna is as generous with the video as with the song, allowing her future Blond Ambition dancers much of the screentime. Vogue is as much a showcase for their incredible talent as for the complex art of voguing itself; not just a dance, but a lifestyle for practitioners of ball culture, where the dance originated.

Best known via its depiction in the 1991 documentary Paris Is Burning, ball culture was practised by a scene populated by the marginalised - largely poor, black/Latino and gay. The ballroom competitions themselves involved “walking”, model-style and usually in drag, as a kind of performance art - with the aim to be as convincing as possible. Their status as social outcasts, survivors banded together as “houses” or “families” (often due to rejection by their actual, homophobic parents) led to voguing as a form of aspiration. Though a tribute to fashion and models, the most popular of figures, it aims to elevate the performer via those poses to something better than they are. Madonna’s video does exactly that - she, the very definition of popularity, puts complete unknowns performing a fundamentally weird-looking underground dance in the mainstream spotlight. Yet, dressed impeccably in timeless suits, their radiant star quality nearly approaches hers. As much as it should ideally fit the song’s everyone-is-a-star theme, they nonetheless got there due to their exceptional talent. Yet as (mostly) gay dancers performing a gay dance, their place in Vogue is also the heart of Madonna’s enduring appeal to the marginalised:

Naturally, the other side to Vogue’s black and white is Madonna’s own presence. Whilst the dance was current, many of Madonna’s shots pay tribute to classic images - such as the Dietrich-esque close-ups, or her portrayal of Horst P Horst’s Mainbocher Corset, bringing the still photo to life. Significantly, the one section where she doesn’t share screentime is during the rap, which consists solely of close-ups of her embodying utterly total confidence, even as she invokes her predecessors’ names. It’s as if she dares you to think any less of her, with the monochrome ensuring a level playing field - viewed in the same way they once were, with the same sense of awe.

Madonna’s return to the MTV Video Music Awards in 1990 was perhaps her single greatest television performance. The incredibly complex choreography - done in authentic French period dress - is as far removed from the writhing Like a Virgin as humanly possible. It’s her equivalent to the Beatles on Ed Sullivan, or Michael Jackson at Motown 25 - a expression of such pure, unique talent it renders even the lipsyncing (as with MJ) irrelevant. But there may just be a message in there, too - her drawing of parallels to Marie Antoinette shows that Vogue is truly universal.

And yet the final word must be that in relation to Madonna’s overall career, Vogue is a single pose in a lifetime of choreography. It may be her legacy, but it cannot summarise her more than any other song; the only thing it represents is the extent of the highs a true cultural icon can scale. “Fame” and “celebrity” aren’t worth much anymore, but Madonna, arguably the most famous woman in the world, has truly earned hers.

Albums: Like a Prayer (1989), The Immaculate Collection (1990), Celebration (2009)
Songwriters/producers: Madonna/Patrick Leonard

As an album, Like a Prayer is often lauded for its incredible diversity - but rarely is it remarked upon how plain odd its sequencing is. This is an album that delights in its jarring transitions - the way it goes from the divorce and domestic violence of Till Death Do Us Part to the sunny, entirely optimistic Cherish within only three songs would be utterly baffling if they weren’t pulled off so well. To call Like a Prayer Madonna’s “divorce” or “religious” album, as it is so commonly labelled, would be to ignore songs like Cherish - which, however contradictory, are a big part of Like a Prayer as a whole. Instead, call it her most personal album - one where Madonna shows her true complexity as an artist by portraying practically the entire range of human emotion.

Cherish is certainly the most outright pop song on Like a Prayer, but its origins lie in the girl-group sound Madonna had been pursuing since Like a Virgin. But where Shoo-Bee-Doo felt cliché, True Blue simply shone - and Cherish takes the style to its final conclusion and greatest heights. It’s the feelings of a woman shedding all the baggage of past failures and relationships for a pure, instinctive infatuation - but one that’s never blind to the need for something lasting, “more than just romance”. Though songs like Vogue and Ray of Light still had the feeling of boundless elation that made so many of her ’80s singles great, such statements of optimism as Cherish were something she’d literally never again attempt. Madonna’s recent Rolling Stone interview shed some light on her present feelings:

Fair enough - one can’t blame her for seeing their optimism as her own youthful naïveté. But she still sings Into the Groove, reinterpreting it mercilessly on the Sticky & Sweet Tour, and Cherish makes for a brilliant transition to the title track on Celebration. Whatever her personal feelings, it’s hardly fanservice when the songs themselves are that great.

Herb Ritts, the man responsible for the True Blue album cover, along with many of Madonna’s most iconic images, had at some point actually become a punchline for photographic style over substance.

But just as Madonna’s huge mainstream appeal doesn’t imply a lack of artistry, nor did the sheer glamour of Ritts’ photography detract from the incredibly evocative nature of his portraits. Though he had no experience in film, Madonna somehow roped him into directing her video for Cherish, and the results are one of the purest distillations of his signature style. Despite, or perhaps because she wears a swimsuit only revealing by 1920s standards, Madonna’s toned figure is as sexy as ever as she rolls around in sand and frolics with mermen. And though shot entirely by Ritts himself on a handheld camera in freezing weather, the blue-tinged monochrome of the beach is nothing but bright and sunny. With none of the extended metaphors of her last two videos, Cherish is just an incredible visual spectacle, but it does it so well that it’s nearly faultless.

(the making of Cherish, from an interview with Herb Ritts - R.I.P.)

Albums: Like a Prayer (1989), The Immaculate Collection (1990), Celebration (2009)
Songwriters/producers: Madonna/Stephen Bray

N.W.A., the seminal hip-hop act and pioneers of gangsta rap outrage, have a lot more in common with Madonna than you’d think… that is, besides both having classic 1989 singles called Express Yourself. When N.W.A.’s version called for rappers not to hold back, to forget the censorship pop music demands, they might as well have been rapping about Madonna - for who else could successfully funnel counterculture and controversy into the confines of a #1 single? Her take on Express Yourself is an insistent denial to anyone who ever took her mock-Material Girl image at face value, and one of the clearest, most inclusive feminist messages ever put to song.

Madonna’s brand of sex-positive feminism is true equality in that it acknowledges men - with no possible accusations of man-hating, any objections can be blamed on the insecurities of domineering macho types. Though she uses every bit of her iconic status to call on women to “make him express himself”, the song’s title, Express Yourself, is also an appeal to male listeners to prove they deserve the women they’re with. “Long-stemmed roses are the way to your heart, but he needs to start with your head” - not the other-way-around double entendre, for material gifts are one thing, but intelligence and empathy go a long way. It perfectly reinforces Madonna’s oft-misinterpreted sexual politics - firstly, that to be desired is empowering, and secondly, that a visible, free-spirited sexuality can be for one’s own sake, and not imply a come-on to any man that’ll have her. As she’d soon whisper on Justify My Love, “poor is the man whose pleasures depend on the permission of another” - and of course, the same goes for women. The heart of the song isn’t a series of demands towards men, but a celebration of womanhood - beautiful, empowered, self-sufficient, but partial to a partner who really can “lift you to your higher ground”… mutually.

Madonna’s original roots may have been in disco, an essentially black form of music, but Express Yourself turns time back to the late ’60s, a perfectly authentic tribute to soul if there ever was one. The album version’s horn section, effortlessly bouncy bassline and generous backing vocals make it a Respect-level anthem for the 1980s, with the difference that Express Yourself (despite having some of Madonna’s strongest vocals) could actually be sung along to. However, Shep Pettibone’s 7” remix was released as the single and video, and included on both The Immaculate Collection and Celebration. With most of the band replaced with synthesisers and house beats - the kind that’d be explored more fully the subsequent year on Vogue - it lacks the album version’s depth, though it’s a little more danceable, more commercial and still excellent nonetheless.

The video for Express Yourself is really the start of Madonna’s Blond Ambition phase - the queen taking place on her throne, revelling in the attention, but always shining the light back onto her subjects. Ever since Material Girl, her ability to pay tribute to the icons before her time and not steal from, but reinterpret them, was much of what cemented her own timelessness. Express Yourself effectively takes the surreal industrial imagery of Fritz Lang’s classic film Metropolis and spins it into something else altogether. It puts Madonna at the top, the epitome of the successful career woman - stunningly beautiful, totally feminine, but also able to dominate in traditionally male roles - as shown by the contrast between her usually curvy appearance and that tense dance in an oversized tuxedo. She oversees a bunch of almost-as-beautiful male factory workers, but while they work, exercise and engage in the traditional competitive male form of conflict resolution - fighting - one man aspires to a little more. Instead of taking part in the macho cockfighting, he looks after Madonna’s adventurous black cat, giving him the balls to take the elevator straight to her bedroom and seduce her. The way I see it, his disregarding of “traditional” masculinity, and his empathy symbolised by the cat are proof of his worth as a lover, a partner - and perhaps Madonna’s crawling to lap up a bowl of milk shows that she is the cat? Throw into the mix a creepy suited observer (her husband? the boss?) and his wind-up horn section and you have a work of art every bit as metaphorically complex as Like a Prayer. And you have to give her credit for gender equality, as always - rather than reducing the female sexuality on show, getting half-naked male models to work out on MTV was a pretty effective way to even out all the eye candy on display. A classic in every sense of the word.