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She’s Madonna: Are these her 40 best singles?

Music makes the people come together, so the song goes. And it’s hard to imagine music without Madonna. It seems like she’s always been there, changing the game and refashioning and refilling herself. Try as we might, it’s just been impossible to avoid her. 

Born in Bay City, Michigan on 16 August 1958 – 13 days and 300 miles away from Michael Jackson’s entry into the stratosphere – the pop journey of Madonna Louise Ciccone officially started four long decades ago when she dropped her first single, the frothy dance jam Everybody, on October 6, 1982. 

Since then, she’s rarely looked back. That’s because Madonna is the mistress of reinvention and, no, you can’t deny her influence (OK, you can fault it but you can‘t deny it), even if she hasn’t done a great deal of much worth lately (too busy adopting half of sub-Saharan Africa, probably). In this age of grand inclusion, and to celebrate Her Madgesty’s 65th birthday, I’ve ranked the top forty ‘best’ singles of her career, taking in every studio album and even that wretched Evita soundtrack. In other words, my choices, my words.

Prepare yourself for a shock as we navigate the highways and the byways of the M40.

You probably saw something online. Madonna’s first album has been marking its anniversary. Four decades since that funky chunky dancefloor debut was released. A different time indeed where a trip to the record store – remember them? – was an adventure.

But 40 years? My, my, the time do fly. 1983 was a year notable by as many arrivals as departures. A twelve-month period that saw Roxy Music and Yazoo call it a day, while Pink Floyd, The Who, The Clash, Haircut 100 and KajaGooGoo all announced they were saying adieu to their frontmen and/or creative forces.

Aside from the self-titled, self-possessed Madonna, the year welcomed, via a golden run of game-changing debut albums, the likes of Bananarama, Cyndi Lauper, Paul Young, R.E.M., Tears For Fears, and George Michael’s Wham! to the world.

With Duran Duran and Culture Club (and a “new” Eurythmics) snapping at their heels, The Police were busy becoming “the biggest band in the world”. While in the solo stakes Michael Jackson’s Thriller really had only one chart rival: Let’s Dance by David Bowie, who celebrated his newfound commercial blandishments by playing his biggest ever shows in Britain just down the road from our house (alas, I stayed at home).

Also, uber-producer Trevor Horn’s ZTT record label leapt into action, as did the chart-slaying NOW compilations – both explored in elsewhere on this blog. Even more ubiquitous and frequently ridiculous, Madonna was probably the most transgressive star of the 1980s and 1990s, giving a voice to the oppressed while offering a bold and brash example of what it means to be free.

That undeniable sense of dancefloor determination to live her life on her terms is why many of her lesbian and gay followers have remained steadfastly loyal to her over the decades. Fittingly, the traditional symbol to mark 40 years is the ruby, a deep red gemstone that symbolises passion, loyalty and devotion. Yet, as was well documented on the occasion of her 60th birthday, in the latter half of those four decades Madonna has tested the staying power of even the most devoted of followers. Indeed, it’s almost impossible to defend or comprehend the ever more desperate hyper-narcissism that bleeds from her social media posts. 

In a strange way, there is a case to be made for classifying current Madonna as an underdog. Granted, it requires overlooking her grotesque wealth and enduring ability to command some sort of an audience with every public move. Yet her status as a top drawer pop star has degraded considerably in the last 15 years, as has her mental health. Her days of hit-making seem long behind her, with  recent albums piled high with more tracks and less to say than any Madonna record that preceded it. Apathy ensues and they plummet down the chart on their second week faster than a greased pig, which some uncharitable sorts might even say looks a lot like Madonna these days, particularly after that bizarre Grammys appearance with the even more confused Sam Smith.

Indeed, whereas she once inspired awe, or at least controversy, her televised appearances of late tend to yield mockery or an avalanche of abuse. It seems that Madonna, once the so-called queen of pop (however meaningless a moniker) and enforcer of the regimentation that comes with that, is no longer controlling her narrative. Which is sort of a shame as in many ways, Madonna is the wellspring of modern-day pop stardom. Delivering bop after bop while being creative, provocative and an unapologetic bitch (her crass term), she wrote the book. 

I suppose, in a way, Beyoncé was on to something when she called her “Queen Mother Madonna” on 2022’s Vogue-quoting Break My Soul, which, after some toe-curling business negotiations, awarded Madge the featured artist credit she craved. Alas, we’re concentrating on Madge’s core catalogue – so in compiling this M40 that means absolutely no rehashes, duets or guest spots on other people’s records. 

Finally enough love?

40. You Must Love Me (1996)

Though it kinda signalled the curtains coming down on her spotty acting career, there’s no particular beef with Alan Parker choosing Madonna to play Eva Peron to shift a few tickets. In the 1990s, big budget movie musicals just didn’t sell themselves, they needed any extra help they could get, even if that meant casting Jimmy Nail. There’s also no problem with said female lead winning the Best Actress Golden Globe over Frances McDormand in Fargo, an oh-so-Hollywood Foreign Press Association choice that AMPAS even more predictably rendered irrelevant when they refused to give Ms Ciccone an Oscar nomination. 

A stately and quietly insistent ballad penned for the film adaptation, if You Must Love Me misses taking the dishonour of being the worst of the Evita soundtrack singles (ola Don’t Cry For Me Argentina or 1997’s Another Suitcase In Another Hall), it certainly chides that its entire mad existence was to push Andrew Lloyd Webber that much closer to an EGOT. The quaking desperation in Madge’s vocal stays the right side of emotional.

39. Celebration (2009)

From the pretty pair of new songs on 1990’s The Immaculate Collection to…well, this is fine if a trifle perfunctory. Recorded for Madonna’s bounteous 2009 greatest hits collection of the same name (a title also swiped for her upcoming will-she-won’t-she tour), Celebration was cunningly intended as a throwback to her early dance anthems. 

Producer Paul Oakenfold’s incessant, four-on-the-floor beat may as well have come from a generic EDM sample pack. “If it makes you feel good, then I say do it,” M tosses off, coming off like a half-hearted Real Housewife too sauced on rosé to actually care one way or another. Benny Benassi added some much-needed sonic interest and rumbling bass on a superior remix, which Madonna was at least smart enough to use both for the music video and in concert.

38. Everybody (1982)

When Madonna handed her New York City pal Mark Kamins her cheaply recorded four-song demo one night at Manhattan’s Danceteria, one song immediately grabbed him. Stuttering into life like a long-lost Tom Tom Club single, Everybody demanded they dance: “She brought [what would become her debut 45] up to the booth,” the DJ recalled. “I listened to it, played it and got a great reaction.” 

A post-disco dance ditty with simple lyrics, infectious production and a star quality that introduced us to a new brand of pop attitude, the song ended up getting her a contract with Sire Records. As the label’s president Seymour Stein remembered, “I was in the hospital, hooked up to a penicillin drip. I listened to Everybody, and I loved it. It was a deal for three singles and an option for albums afterward. I would have gone down to the bank and withdrawn my own money to sign her if I had to.”

37. Medellín (2019)

Going south, this one’s named after the Colombian city where its hunky guest star originates. Medellín was also the lead single from M’s most recent studio set, 2019’s Madame X (the so-called International deluxe edition features a Bob Dylan down the disco oddity called Funaná, which mourns the loss of various fallen popsters such as Bowie, Freddie, Whitney and her one-time collaborator Prince). 

The album is a confused auto-tuned-to-buggery indulgence (too many garish digital vocal effects that sound like a Gen-Z wannabe’s M imitation), its first 45 was nonetheless a curious understated melange. Madonna and Maluma crafted a Latin pop banger that was slinky, sensual, and outrageously sexy. Forget the desperate crassness of choosing the hot-in-every-way Latino superstar —the two have a mother and son chemistry that just crackles in its incestuousness. And when the old dear sucks his toe in the video it’s hard not to get a little tingly in the nether regions. Cha-cha-cha.

36. Ghosttown (2015)

This is not an apocalyptic love song. Oh no, actually it is. It’s a shame that Madonna’s unlucky 13th album, the rather over-long Rebel Heart, didn’t spawn any real hits because it had two half-decent if factory-pressed sounding singles in Living For Love and Ghosttown. Alas, the project was doomed from the get-go when she was plagued by a series of embarrassing song leaks from an extremely well placed source. Despite taking measures to mitigate the effects of having material online months ahead of schedule, the damage was already done.

With its haunting atmospherics and doom-laden lyrics depicting the “darkest days” in a post-Armageddon world, Ghosttown was eerily prescient of Trump-era despair. An steadily unfurling ballad with a powerful message of resilience, on it she paints unfathomable images of destruction but refuses to lose hope for her and a partner.

35. Masterpiece (2012) 

This is, hands down, the most under-appreciated single of Madonna’s career. A sweet, gentle love song with a Spanish guitar loop, slight beat and flowing melody, filled out by a gorgeous orchestration. Madge’s voice sounds particularly sharp on Masterpiece, without the distracting digital correction of most of her 21st century output. The theme song for her critically panned film W.E., she may have been thinking of the abdicated King Edward VIII — or indeed the current hogger of the throne, her sometime countryside acquaintance King Charles III — when she wrote “Honestly, it can’t be fun / To always be the chosen one”, but the message applies just as much to Madonna herself. 

For most of the MDNA album she seemed determined to demonstrate that a 50-year-old mother of four can still cut it with the kids at the club. Yet, perversely, she sounds most at ease when she calms down a bit and acts her age, which she does on this aptly-titled flop. A prime contender for reissue should M ever consider a second ballads collection to follow 1995’s Something To Remember. Talking of which…

34. I Want You (1995)

OK, enough of one-word titles for now. Strictly speaking this one-off team-up for with Bristolian trip-hoppers Massive Attack only got as far as the promo and video stage, its commercial release nixed at the last minute due to “copyright issues” with the song’s owners Motown. A sparse, moody melodrama of romantic and sexual yearning, M + M reinvent the old Marvin Gaye chestnut with a noir Bond-esque vibe – more than enough to fill a man’s void of lustful dreams for 6 and a half minutes (count ‘em) in one of her most understated and haunting songs to date. 

Three decades on, and at just 81 beats per minute, perhaps I Want You was too quiet, too weird, and too good, and thus too un-Madonna for the masses to embrace. It only makes sense that a song about longing would be left unloved.

33. Give It 2 Me (2008)

There were times on 2008’s underwhelming Hard Candy when superstar producers Timbaland, Justin Timberlake, and the Neptunes commandeered Madonna’s sound that reduced her to a bit player on her own record (see the godawful JT collaboration 4 Minutes), but the emphatic Give It 2 Me showed that she was still in charge.

Even a bit of silly goofiness during that “get stupid” bridge with Pharrell can’t deny the insistent bounce.

32. What It Feels Like For A Girl (2001) 

Directed by then hubby Guy Ritchie, the cod-violent video for this woozy track was the second Madonna promo to be banned by MTV. This midtempo beauty saw M speak about society’s double standard toward women, and addressed general hurtful myths about female inferiority.

To emphasise the message, it opens with a spoken word sample of Charlotte Gainsbourg’s meditation on gender from the 1993 film The Cement Garden, making Madonna’s point crystal-clear. “Our generation has been encouraged to grab life by the balls, be super independent,” Madonna said in 2001. “And I realised that smart, sassy girls who accomplish a lot are really frightening to men… That’s also what that song is about: swallowing that bitter pill.”

31. Bad Girl (1993)

With a characteristically graceful, tap-dancing Christopher Walken playing her guardian angel, Madge gives a passable performance in Bad Girl’s downbeat David Fincher-directed video as a guilt-ridden woman who pursues a series of unsatisfying one-night stands and winds up paying the ultimate price for her hedonism. The song itself is a sombre, sophisticated ballad sung from the perspective of the soon to be dead woman, drawing curious parallels with ABBA’s The Day Before You Came and its “matter of routine” laundry list in reciting the miserable minutiae of an unfulfilled life: “Drunk by six/ Kissing someone else’s lips,” she warbles. “I’m not happy when I act this way.”

Co-author and production pal Shep Pettibone later recalled how amazed he was at Ciccone’s ability to write and record quickly: “Madonna has an incredible mind. She locks the melody into her head and memorises the words immediately. Her stories were getting a lot more serious and intense, driving the creative direction of the songs into deeply personal territory.”

30. Oh Father (1989)

“Family is everything. Family comes first,” Madonna once said. “It’s not what I expected it to be, but nothing ever is.” 1989’s Like A Prayer had heavy meditations on the theme like the lush piano ballad Promise To Try and this handsome weepie. Passed over for the coquettish Dear Jessie 45, Oh Father didn’t make it out as a single in most of Europe until its inclusion on the Something To Remember ballads collection in 1995. 

The lyrics deal with the presence of male authoritative figures in Madonna’s life, most prominently her father, Tony. Her relationship with the senior Ciccone had soured, after her mother’s death in 1963 and his remarriage two years later. David Fincher directed its wintry monochrome video. She said: “I just wrote the song, it’s up to others to interpret them to mean what they want them to mean.”

29. Die Another Day (2002)

Analyse this. American Life — the folky psychobabbly one where she looked a lot like the bastard rebel child of Che Guevara and Patti Hearst on the cover, and probably the most divisive album of Madonna’s career — produced one of her most ridiculed singles in its title track.

But its predecessor, the theme tune to the James Bond movie of the same name was a triumph of sorts, creatively if not critically. Fair play to Madge — who also had a squeaky cameo in the film — for not going gung-ho down the obvious Shirley Bassey/Tina Turner route, Die Another Day is an exhilarating electroclash of stuttered strings and interpolating synth swirls and was the top selling dance song in the US for both 2002 and 2003.

28. Don’t Tell Me (2000)

Madonna surprised listeners with this twangy take on country dance electronic – countrytronica? But the second single from Music originated in another genre entirely. Don’t Tell Me began as a torch song called Stop demoed by her brother-in-law, singer-songwriter Joe Henry, that Madge and French producer Mirwais reworked during the album’s London sessions.

A simple plea asking her lover not to control her, the singer says she was initially drawn in by “the sentiment of it, the defiance, the attitude of it – ‘Don’t tell me to stop,’” she said. “Just loved that.” In talking about the differences between his version and hers, Henry said, “I realised that, you know, groove is everything.” Weirdly, Boris Johnson quoted its poetic lyrics in a 2003 interview with The Guardian, but don’t let that put you off. Sometimes even a self-obsessed wanker knows a great tune when he hears one.

27. Bedtime Story (1995)

Icelandic pop pixie Björk Guðmundsdóttir has long been a Madonna fan. “I’m not going to get into the things she’s done for women,” the former Sugarcube told Rolling Stone. “You’d fall asleep, there are so many.” However, Björk wasn’t sure how to approach what was the almost title track for 1994’s Bedtime Stories: “I couldn’t really picture me doing a song that would suit her. But on second thought, I decided… to write the things I’ve always wanted to hear her say.” 

What emerged was an atmospheric and entrancing exploration of emotional impulses that transcend language – “Travelling, leaving logic and reason,” Madge sings. With its hypnotic house tinges helping to pave the way for future EDM experiments, M performed it at the Brit Awards and despite looking rather top-heavy, she stayed upright throughout, unlike ten years later.

26. The Look of Love (1987)

Inspired by James Stewart’s glances at Grace Kelly in Hitchcock’s Rear Window, this moody and mysterious Who’s That Girl? soundtrack song sits on an occasionally interesting tide of tropical washes. The Look Of Love is also one of Madonna’s most overlooked songs, inexplicably excluded from Madonna’s 1995 ballad collection Something To Remember. One assumes its author isn’t too keen on it, having not performed the song live since its year of release.

25. Deeper And Deeper (1992)

Madonna took a deep-house dive with the second single from Erotica, produced by club-remix legend Shep Pettibone. Its retro-disco video was riddled with cameos, including her now manager Guy Oseary, Sire Records chief Seymour Stein, longtime friend and actress Debi Mazar and adult film director/DJ/drag diva Chi Chi LaRue. The song itself plays like a sequel to Vogue — even quoting from that earlier hit toward the end — it pours on the dance-floor drama and even sports a fabulous flamenco breakdown. Oh, olé.

24. Human Nature (1995)

Long before Demi Lovato gave us Sorry Not Sorry, the unapologetic bitch that is Madonna responded to her critics with this defiant declaration that makes a lyrical nod to Express Yourself. Produced with hip-hop soul flavour by early Mary J. Blige collaborator Dave Hall, it goes straight-up gangsta on you. The video’s funny and fab too.

23. Frozen (1998)

Ushering in the ambitious, ambient Ray Of Light era, that album’s first single was a real revelation, sounding unlike anything Madonna had ever done before. Madge and new cohort William Orbit created a mystical forest of sonic enchantment — sweeping strings and all — Frozen possesses an almost operatic grandeur, and it never fails to give you chills.

22. Live To Tell (1986)

In addition to serving as the first single from True Blue, this song was featured in the film At Close Range, starring Madonna’s then-husband, the wannabe gangster and future Milk man Sean Penn. Setting the moody tone for other movie ballads that she would go on to do — including 1992’s This Used To Be My Playground and 1994’s I’ll Remember — this aching confession found her displaying greater depth and maturity than ever before.

21. Sorry (2006)

As I mentioned earlier, arch Pet Shop Boys aficionado Stuart Price wasted no time in interpolating his love for the seminal synth duo on Confessions on a Dance Floor, which was largely recorded in his West Kilburn flat about five blocks from mine at the time. And Neil Tennant was quick to capitalise. With its percolating air-lifting groove, “Jump sounds like it’s got a bit of West End Girls in it to me,” the PSB frontman told this author at the time.

“But the song we thought sounded most like us was Sorry (1987’s Catholic-castigating It’s a Sin to be precise, which M’s Who’s That Girl dethroned from pole position), so we asked to remix it and within 12 hours we were doing it,” prompting Neil to “add a load of vocals,” with him playing the “pathetic guy” in the lyrics, because “I’ve always wanted to sing a duet with Madonna.” Madge told him, ‘That was really cheeky of you but it worked,’ and went on record as preferring it to the original disco ditty (she later disowned the song as “retarded.”), even sampling his dulcet tones on the Confessions shows and subsequent live album. “I felt quite proud that I was in her show,” he beamed. “She called it a ‘killer remix’.”

20. Take A Bow (1994)

After the salaciousness of the whole Sex book and Erotica era, Madonna classed up her act in a big way with a beautiful Babyface-produced ballad. She even works a bit of Shakespeare into this contemplative and downbeat soother from the under-appreciated Bedtime Stories album. It worked. Take A Bow spent seven weeks at the top of the Billboard Hot 100, making it her longest-running No. 1 single ever. At first it sounds like a comparison between a broken relationship and a curtain call, but the sumptuous video pivots the story to paint the bad guy as a deadly matador. It’s maybe the most elegant thing Madge has ever done.

19. La Isla Bonita (1987)

Bonita is Spanish for pretty, and this island-breezy ditty is certainly one of the loveliest tunes that Madonna’s ever done. Exploring Latin pop long before it became trendy, the song — an indelible fixture on her tours — inspired everything from her own Who’s That Girl to Lady Gaga’s Alejandro. Si, Señorita.

18. Borderline (1984)

This is one of six tracks on 1983’s Madonna debut that were produced by Reggie Lucas, who had previously worked with R&B artists like Stephanie Mills and Phyllis Hyman, and was remixed by Madge’s then-boyfriend John “Jellybean” Benitez. Madonna — whose early cleverly anonymous-sleeved singles were getting played on black radio back then — has never sounded more genuinely impassioned than on the divine Borderline. 

17. Drowned World/Substitute For Love (1998)

Between 1994’s Bedtime Stories and 1998’s Ray of Light, Madonna became a mother for the first time, giving birth to her daughter Lourdes. Marking the moment Material Girl evolved into the Maternal Girl, she addressed that life-changing experience on Ray of Light‘s opening track and third single, a moody ballad exploring epiphanies about fame and family. “I got pregnant, and the whole idea of giving birth and being responsible for another life put me in a different place,” she said that year. “People have been obsessed with the idea that I am always reinventing myself, [but] I’d rather think that I’m slowly revealing myself. The song updated ’80s Madonna with an ambient soundscape by maverick maestro William Orbit.

16. Crazy For You (1985)

“Ah, it sings!” ran the review in Smash Hits magazine. Indeed, Madonna had yet to prove that she could sing you a love song until Crazy for You. The only slush puppy she’d even attempted was a cover of Rose Royce’s Love Don’t Live Here Anymore on 1984’s Like a Virgin, but that wasn’t a single until over a decade after the event. But this huge hit from the soundtrack to the frankly dodgy Vision Quest movie was a career highlight. Although she would become a more accomplished singer on future ballads, none of them were as commercially successful as this, and that raw, soulful yearning is something that they certainly can’t teach you in voice class. Crazy For You never actually appeared on any of her studio albums either.

15. Express Yourself (1989)

“Come on girls, do you believe in love?” Well, in ‘89 Madonna had something to say about it, when Express Yourself was released as the second single from the Like a Prayer album. “Don’t go for second best baby, put your love to the test,” she preaches, making her definitive feminist statement.

The original album version — which she co-wrote with early collaborator Stephen Bray — is a slightly bass-lite horn-heavy blast, but it’s Shep Pettibone’s housed-up remix you hear in the epic David Fincher-directed video that lifted the single to its higher ground.

14. Ray Of Light (1998)

Madge may have already reigned over the pop world, but on the Grammy-winning title track of her Ray Of Light opus she was transformed into a goddess of the universe. Based on Sepheryn by the ancient English folk duo Curtiss Maldoon, the song was revamped into the ultimate trance dance with production by William Orbit. It brilliantly captures the spiritual glow of Kabbalah Madonna, who gives us a little piece of heaven.

13. Lucky Star (1984)

With this single off her self-titled debut, Madonna hit the Top 5 of the American Billboard Hot 100 for the first time. One of five songs on her first album written solely by the singer, this radiant, pulsating twirler feels as if it comes equipped with its own disco ball. Stuart Price’s Confessions Tour (2006) reimagining is a thing of thunderous shimmering beauty.

12. Like A Virgin (1984)

A confirmed and committed David Bowie fan, Madonna nabbed Chic’s Nile Rodgers for production duties on her second album, Like A Virgin, chiefly because he’d just provided The Dame with the biggest selling record of his career, 1983’s Let’s Dance. Written by the hitmaking team of Tom Kelly and Billy Steinberg, Like a Virgin’s title track became so much more iconic than the album from which it was culled — from the vintage video in Venice to those unforgettable performances at the MTV Video Music Awards or at the BBC‘s Top of the Pops (above).

And while those saucy nudge-nudge wink-wink lyrics may feel relatively innocent compared to Justify My Love and Erotica, Madonna’s first Billboard No.1  paved the way for female pop artists — from Janet Jackson and Britney Spears to Rihanna — to be sexually provocative. Right or wrong, no one had to act like a virgin anymore.

11. Papa Don’t Preach (1986)

Dealing with teen pregnancy, this No. 1 single from True Blue found Madonna tackling a social issue for the first time — and she did it in strutting style. The string arrangement adds a classical gravitas just in case you didn’t think that she was serious about keeping her baby. If you don’t know this sing you must have been living under a cock.

10. Beautiful Stranger (1999)

This is a divine slice of William Orbit-produced kitsch perfection, from the movie Austin Powers: The Spy Who Shagged Me. Possibly the greatest Number 1 that never was for Madge, Beautiful Stranger is her tenth biggest seller in Britain and the fact that it continues to excite me almost two decades after first hearing it is, in my view, testament to its capacity to transcend the boundaries of definition. 

9. Material Girl (1985)

Like many of Madonna’s signature hits, Material Girl — which spawned her most famous nickname, whether she liked it or not — is probably known as much for its video as the song. I mean, who can ever forget M doing her best Marilyn Monroe in that Diamonds Are a Girl’s Best Friend homage? The single itself is kitchy synth-pop perfection of the likes only helium-nuanced Madge can pull off.

8. Hung Up (2005)

This infectious lead single off Confessions On A Dance Floor marked a comeback for Madonna after the relative flop of American Life. The all-conquering Hung Up became her record-tying 36th top 10 hit, and she would go on to break the record previously held by Elvis Presley — who just happened to go and die on Madge’s 19th birthday — with 2008’s 4 Minutes. Built around a hypnotic sample from ABBA’s Gimme! Gimme! Gimme! (A Man After Midnight), it gets you caught up in a galloping disco rapture that still sounds contemporary 13 years on. It’s also her biggest selling single in the world… ever.

7. Music (2000)

Madonna’s music had been making all kinds of people come together throughout her career. But this squiggly electro boogie — her last American chart-topper — was a full-circle moment that took her back to her beginnings as a DJ-loving New York club kid in the early ‘80s and showed that, although now a mother of two in her 40s, she could still rule the dance floor. The weird, vaguely eerie electro-pop produced by Mirwais makes this one of her most eccentric hits ever. But whether you are the bourgeoisie or the rebel, the message is universal..

6. Justify My Love (1990)

Probably the most radical single of her career, Justify My Love went so far against the pop establishment that it is a testament to Madonna’s dominance that it still went No. 1 in her homeland. A spoken-word ode to releasing your inner freak that grinds to the sleaziest of hip-hop beats is not supposed to justify such mainstream love. But this Public Enemy-sampling song — co-written by Lenny Kravitz, who also moans orgasmically in the background — was so hot that not even MTV’s video ban could stop it from climaxing.

5. Open Your Heart (1986)

As much as Madonna may be known for her more titillating songs, she has also been capable of pure pop bliss. That can be heard on hits like True Blue, Cherish and, best of all, Open Your Heart, which updated a 1960s girl-group giddiness with an ’80s sheen. No doubt, she has rarely sounded more open-hearted than she does here

4. Into The Groove (1985)

“And you can dance!” Madonna may have never truly conquered the acting world — the dialogue-free easy ride of Evita notwithstanding — but she definitely made some killer movie music. Case in point: Into the Groove, which was featured in her most watchable film Desperately Seeking Susan.

Although the track — which grooves along a bumping synth-bass line — was technically the B-side to Like a Virgin’s Angel in the US, it’s always been clear which of those cuts made the A-list. Amazing to think the finished record is basically a demo that Madonna didn’t know what to do with, ITG is also her biggest selling single ever in the UK and its opening lyrics gave its name to M’s 1987 remix album, You Can Dance.

3. Erotica (1992)

There was a lot going against the title track from M’s fifth studio album: It was released just before her scandalous Sex book, and its video was banned from MTV. But this dark and sexy single, which picked up where Justify My Love left off, was just about the boldest move she could have made at the height of her career. Playing like your dirtiest fantasy set to music, it also introduced the pop-diva alter ego: Before Mariah gave us Mimi and Beyoncé gave us Sasha Fierce, Madonna gave us the dominatrix Dita. The live version that opened 1993’s Girlie Show was pretty squelchy too.

2. Like A Prayer (1989)

Slyly influenced by Bowie’s less good 1986 single Underground (that one from Labyrinth that isn’t Magic Dance), Like A Prayer also marries a gospel choir chorus to synth basslines and ricocheting beats. From the moment she sings “Life is a mystery, everyone must stand alone” atop that solemn organ, LAP goes on to achieve a spiritual transcendence that makes this her supreme single, with the artist at the peak of her powers. Having grown up Roman Catholic, Madonna balances the sacred and the secular here to ecstatic effect, with gospel great Andraé Crouch’s choir really taking it to church midway through. The whole thing takes you there again and again. Classic Madonna.

By the way, although Madonna and then Warners label mate Prince duetted on Love Song, one of the lesser Like A Prayer album tracks, it wasn’t until a 2014 interview with LAP’s producer, Patrick Leonard, that it was revealed it’s actually the Minneapolis marvel on distorted guitar at the very beginning of the title song before the door slams. There are remixed versions with a bit more of the Purple One’s uncredited axe work, as well as the flip side, Act Of Contrition, which contains a Prince guitar solo constructed mostly over a backwards sample of Like a Prayer. Prince is also said to play on the US and Australian single Keep It Together, of which this toppermost tune was originally recorded as its B-side…

1. Vogue (1990)

Initially — incongruously — planned as a mere B-side to the US single Keep It Together, this enduring No. 1 smash that is Vogue may not be everyone’s favourite Madonna single, but it could be the most iconic. A lot of that has to do with the classy monochromatic video, which brought the underground club culture of gay voguing balls to the masses. But this pumping house banger — from the Dick Tracy soundtrack I’m Breathless — inspires everybody to be something better than they are today. All you have to do is strike a pose — there’s nothing to it. 

Marilyn gets referenced once again and is mentioned specifically in Vogue’s bridge, where Madonna conjures up a spoken pseudo-rap list in which she references sixteen shining stars from Hollywood’s Golden Age. Here’s the first bit…

“Greta Garbo and Monroe, Dietrich and DiMaggio. Marlon Brando, Jimmy Dean, on the cover of a magazine. Grace Kelly, Harlow, Jean, picture of a beauty queen. Gene Kelly, Fred Astaire, Ginger Rogers, dance on air…” 

They had style, they had grace, what the hell has she done to her face?

Steve Pafford

NB No, I didn’t forget Holiday. While it’s undoubtedly one of her key dance anthems and a prototype for everything from Into The Groove to Living For Love, like Bowie’s Heroes I’m more than happy never to hear it again. Overkill is a killer. 

Alive — 1990, 1993, 2000, 2001, 2002 (theatre play), 2003 (BBC TV appearance), 2004, 2005, 2006, 2008, 2012 (all London); 2004 (Arnhem, The Netherlands); 2016 (Sydney, Australia). 2023? Thanks but no thanks…

You see: Why Madonna’s Ray Of Light is her masterpiece is here

Strike A Pose: Why Vogue is Madonna’s finest 45 is here

Causing A Commotion: 30 Stupid Things Madonna’s Done is here and here

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