A screengrab of Madonna from the Vogue video, showing her posing in close-up with blond hair and dangling jewelled earrings

40 years of Madonna: the best of her best

Madonna is celebrating forty years in the business – well, she’s not actually doing that much other than post a couple of Instagram Stories, but the fact remains her first single Everybody was released forty years ago this week. Forty. FORTY. Four decades of Madonna. Truly we are blessed.

It’s only recently Madonna has started looking back at her career with any depth. She’s always prided herself on advancing, not regressing, despite the best efforts of the media (and her fans let’s be honest) to rake back over her many, many achievements. She’s resisted the slide into heritage act that’s befallen many of her peers. No ‘Songs from the Great American Songbook’ for Madonna – and I’m praying she never goes orchestral. She sees herself as a contemporary pop star, in a constant state of evolution. She’s often questioned on why she still creates pop music, using modern sounds and working with the biggest producers du jour. To her, it’s simple: it’s what’s she’s always done. Her body may have aged, she may have become a mother, and an inspiration to the pop girls and guys who followed, but she’s not a museum piece, she has (until recently) shown little interest in retreading her biggest hits. 

But post-60, with a movie of her life supposedly on the cards, and following a series of injuries that stymied her Madame X theatre tour – itself a much more intimate set of gigs than the extravaganzas she was more accustomed to staging – there’s a sense she’s taking stock, reappraising her legacy, and spending at least some of her time with one eye on the past. Previously, as far as Madonna was concerned, I suspect, her legacy was for others to pore over – she was very busy with the business of making history, not studying it.

To celebrate her forty years in music, movies, the tabloids, and my headphones, I’ve selected a few categories, some quirky, some clichéd, and picked out her best of the best, some honourable mentions, and, because I believe glowing reviews lack credibility and relentless positivity is almost as toxic as negativity, pointing out a few stinkers along the way.


The contenders: Lucky Star; Material Girl; Papa Don’t Preach; Who’s That Girl; Spotlight; Like a Prayer; He’s a Man; Erotica; Survivor; I Want You; Substitute For Love; Music; American Life; Hung Up; Candy Shop; Girl Gone Wild; Living For Love; Medellin

BEST: With a couple of exceptions, Madonna albums open up STRONG; there are some classic tracks in this line up, with intros that set the tone for what’s to come. The cosmic shower of Lucky Star, the urgent, passionate strings of Papa Don’t Preach, Music’s spoken opener in electrically assisted Madge baritone, counting us in before Medellin kicks off, the scratched record on Erotica, Hung Up’s ticking timebomb, Substitute For Love’s new age underwater dreamscape. I even like Candy Shop. But. BUT. For me, nothing tops that pushy, confident bash of the drums of Material Girl, the ultimate love letter to Eighties excess and self-preservation. Its parent album, Like A Virgin, would be Madonna’s first LP release as a bona fide star, and Material Girl’s assured swagger is the perfect statement of intent. No prisoners taken, no wallet left unchecked, no heart left unbroken. You had to wait another year or so before Into the Groove gave us Madonna singing ‘now I know you’re mine’ but we knew it was true way before that, right here, on the best non-Chic song Nile Rodgers ever got involved with. We weren’t just living in a material world, this was Madonna’s world.

LEAST LOVED: Despite perhaps one of the finest long spoken and dramatic intros of Madonna’s career, harking back to the height of her Eighties Catholic mania, I’m afraid as a song, Girl Gone Wild is the worst thing she has ever recorded.


The contenders: Everybody; Stay; Love Makes the World Go Round; Act of Contrition; Vogue; Rescue Me; Secret Garden; Take a Bow; I Want You (orchestra; version); Lament; Mer Girl; Gone; American Pie*; Easy Ride; Like it Or Not; Voices; Celebration; Falling Free; Wash All Over Me; I Rise.

BEST: Madonna’s closers make a pretty impressive collection too. Much has been made of Madonna’s ability to make an entrance, her career a series of first impressions with each so-called reinvention, but she’s pretty adept at a decent exit too. Her first ever single is, strangely, how she closes her debut, but it’s rare for the final track on an album to see her in party mode. For the most part, Madonna’s closers have been introspective and subdued, something for us to chew over. Whether she’s rolling about on her mum’s grave in Mer Girl, ditching her lover on Take a Bow, heading for immortality on Lament, or contemplating her own legacy on Wash All Over Me, Madonna usually likes to leave the room on a downer. ‘You’ll miss me when I’m gone’ she seems to be saying. But of them all, her finest French exit is Easy Ride, a stark electroballad that seems drenched in both hope and self-doubt, a look to the future that acknowledges that she won’t be here for some of it. She was 44 when parent album American Life came out, and if there’s ever been a more dreamy and euphoric midlife crisis than Easy Ride, I am yet to hear it.

LEAST LOVED: Love Makes the World Go Round (1986). She performed this at Live Aid. This. I can only assume nothing else off True Blue was ready.

*American Pie ‘officially’ closes Music (2000) on editions other than the US version after Madonna was ‘talked into it’ by the suits at her label. However, as Gone is clearly the intended closer, it gets to be in the running. Irrelevant, tbh, as I don’t like it.


Madonna doesn’t have many standalone b-sides – it was common through much of the 80s to whack an old track or an album cut on the B so that fans or DJs spinning the 7” would have another vaguely recognisable song to hand, plus it helped showcase whatever album they were trying to flog. But if we’re talking bonus tracks, b-sides, or stuff that didn’t make it onto a studio album, for me, this would be Fighting Spirit, a Confessions offcut that was released on a physical edition, I think. To say it comes from sessions of an album full of lush instrumentation and disco vibes, it’s moody, weird and very minimal. 

Honourable mentions: Erotic, the version of Erotica that came with the notorious SEX book; Super Pop; History; Supernatural (Sly & Robbie remix)

No: Ain’t No Big Deal. Was the B-side of numerous Madonna singles in her early days. The very definition of nothing to write home about, interesting only because it was one of her early demos that got her a deal.


As impressive as Madonna’s backlist is, she’s not immune to filler, songs making up the numbers that would never see the bright lights of the Top 40. Of all her LPs, only one sounds like any song could’ve been a single (save for its closer, I suppose, but let’s not split hairs), and that’s Like A Prayer. Madonna got deep for the first time and lyrically and creatively she has seldom been so powerful since. It’s not an album I revisit much these days – it needs a remaster – but first three singles aside, Till Death Do Us Part is its crowning glory. A white knuckle ride through a stormy and violent relationship, TDDUP’s jaunty, jangly and slightly too fast backing track sounds like the constant niggling doubt over whether to leave a hotheaded lover, a panic attack that won’t quit. Madonna’s delivery of the angsty, poetic, and devastating lyrics is one of her strongest early performances. Autobiographical? Who knows? She’s distanced herself in recent years from the lurid tabloid claims about her first marriage to infamous bellend Sean Penn. It may not be her own story she is telling, but this track feels like Madonna opening herself up to us for the very first time. It’s as urgent and uncensored as a hurriedly scribbled diary entry, ending as downbeat and inconclusive as life itself. 

Honourable mentions: I’ll pick one from each album, unless the non-singles were crap. Over and Over; Where’s The Party; Thief of Hearts; Love Tried to Welcome Me; To Have Not to Hold; Impressive Instant; Easy Ride; Future Lovers; She’s Not Me; I’m Addicted; Body Shop; Come Alive.


We all know the same five hits that Heart, or Magic, or Radio 2 love to play, as if she wasn’t the woman with over 60 Top 10s alone. Anyway, song that deserves more credit that never gets played or talked about? Angel, off Like A Virgin. Overshadowed in the US by its b-side Into The Groove, ignored on all her hits collections, with no video made for it, it’s incredible to think Angel was once in the running to be its parent album’s lead single. It’s a cute, gushy bop in the vein of Blondie’s Dreaming or Sunday Girl, quite girly and submissive for the woman who would become the most powerful popstar on the planet. Lyrically, it flexes a similar muscle to Cherish, another much underrated single which suffers from Madonna no longer liking it and ignoring it in live shows. You know how she is.

Honourable mentions: Dress You Up; Cherish; Rescue Me; Fever; Bad Girl; The Power of Good-Bye; Give it 2 Me – all ACTUAL Top 10s


The contenders: Madonna has had more singles peak at Number 2 in the UK than any other artist (fellow camp icon Kylie is second) and often they’re better than the number 1s. Crazy For You (twice); Borderline; Holiday; Live To Tell; Hanky Panky; Justify My Love; Ray of Light; Beautiful Stranger; Me Against The Music; American Life; Hollywood.

BEST: Ray of Light should have been a Number 1. 100 per cent. So it’s that. Beautiful Stranger, Live To Tell, and Justify My Love – with its X-rated video that made headlines, arguably the beginning of Madonna’s delicious descent into sex’s dodgy underbelly, and Lenny K on backing vox – are all incredible songs in their own right, and should probably have topped the chart too. Beautiful Stranger was beaten by S Club 7’s horrific debut, which makes the failure sting all the harder – but Ray of Light just sounds like a Number 1. So it’s Ray of Light.

LEAST LOVED: Crazy For You is an absolute dirge. Her worst ballad. The kind of song non-Madonna fans like. (Similarly, Borderline has the not remotely coveted status as being that ‘I don’t really like Madonna but I do love…’ song that people too repressed to watch the Erotica video love to claim.) Ugh. Groove Armada did a good version of it, though, for a Radio 1 compilation in the Noughties.


Whoa. Thirteen contenders: Into the Groove; Papa Don’t Preach; True Blue; La Isla Bonita; Who’s That Girl; Like A Prayer; Vogue; Frozen; American Pie; Music; Hung Up; Sorry; 4 Minutes.

BEST: It’s Vogue. Is it her best song? Possibly not. Almost certainly not. But is it a tour de force, a song that could only ever be a Number 1, or a massive flop, with no in-between? Yes. It’s a relentless, pulsating kick in the bollocks of your personal dance floor, and it’s actually about dancing, and a dance move in particular, so should really be a novelty record. Perhaps if it had been sung by anybody else, wit more nudging and winking, it would be played between the Vengaboys and Las Ketchup at school discos. But this is Madonna, who always takes everything seriously. And vogueing isn’t the Macarena – it’s iconic, it’s artistic, and… it belongs to someone else, but you know how Madonna likes to be ‘inspired’. But back then, it was an almost cynical, calculated, chemical weapons attack on the Number 1 spot that could probably only have ever been a hit in 1990. And it is definitely her best Number 1. Music has similar bombast and, when you think about it, is also a bit of a novelty song, and even has a reference to a dance move in ‘boogy-woogy’ – but Vogue is Vogue. Interesting also that Madonna’s only ‘ballad’ Number 1 is Frozen, but is it her best ballad? We’ll see. Hung Up is a thing of beauty and was a moment, but… I could go on. Regardless, Vogue wins.

LEAST LOVED: For me? 4 Minutes, her last ever chart-topper, literally scorched the earth meaning she can never hit number 1 again. A soulless collab with a peak ‘soup of the moment’ Justin Timberlake, and a ‘slightly faxing this in’ Timbaland. And it wasn’t even four fucking minutes long.


Madonna is one of the few pop artists to have occupied every single position in the Top 10 for at least one week. She has the most successive Top 10s than any other singer – racking up 36 consecutive Top 10 hits between 1984 and 1994. Altogether, she’s scored 63 of them (including those 1s and 2s), so what’s the best of the ones that didn’t make it to the Top 2? It’s not her last ever, Celebration, from 2009. And it’s not her first, Holiday, from 1984. Honestly, if I think about, which one is the best of the rest? For impact? For longevity? For the visuals? Should it be Express Yourself? Second single off Like A Prayer, remixed beyond recognition but into the history books for single release (although the official single version is a slight rejig of the album version, not the proto-Vogue slow house banger that packed dance floors) – and it only got to No.5. What cloth-eared pricks the general public are. Like A Virgin? Her first US chart-topper, the song that made the world sit up and listen? Deeper and Deeper’s Vogue-riffing disco explosion? No, none of those, but they rate highly. It’s a song from her first peak. A video set in a peep show. A brunette wig that is worn for mere seconds but made front page news because we lived in an era where Madonna’s assumed change of hair colour would be a segment on the evening news. An early appearance of a conical-boobed basque. And a mildly inappropriate flirtation with a pre-teen heartthrob. Watch out! It’s Open Your Heart, an American Number 1 which stalled at Number 4 in the UK, sticking there for three weeks. What a song. (The video version is the superior, and was recently included on remix album Finally Enough Love, making it commercially available for the first time.)

LEAST LOVED: I have never listened to This Used to be My Playground all the way through, and I never will.


Best single not open for discussion: it’s Live to Tell, True Blue’s only slowie. There’s magic here. How much of it is hers and how much is Patrick Leonard’s and the blurring of their mutual mythology is unknown, but she sells this like that secret really has been burning inside of her.

As for best album track ballad: Paradise (Not For Me). Like Live to Tell, this has the air of Madonna striding into someone else’s backing track – Mirwais in this case – and sprinkling on her stardust. It’s a credits-rolling, melancholic flick through a photo album. At a funeral. Lovely. 

Honourable mentions: You’ll See; Love Tried to Welcome Me; Promise to Try; Substitute for Love.

Meh: Take a Bow. A good song, but she’s never really sold it for me and it destroyed her run of Top 10 singles in the UK, stiffing at 16. I bear a grudge.



Madonna has worked with some of the best producers in the business, but if we’re talking collabs with other artists, duetting, sharing vocals, or doing a feature, I think she works better alone. Be Careful, a duet with Ricky Martin on a song originally just Madonna and left off Ray of Light, is pretty nice but would be better as a Madge solo. Heartbeat, off Hard Candy, which features Pharrell doing the odd shout out in the background, is peppy and cute but doesn’t feel like a Madonna song. Me Against the Music, her first big name collab and her first shared credit on a chart hit, works best in remix form but it’s clear Madonna was merely added at the last minute. Her work with Avicii for what became Rebel Heart was quite exciting in demo form, and a lyrical return to full power, but perhaps lacked Madonna’s musicality, and was sanitised into blandness for the final versions. So, for me, nothing doing here.


She just released an album of 50 remixes from across her career, but left off the one I like the most: the atmospheric, slightly funked up Stereo MCs take on her 1998 ‘comeback’ Frozen. Very different from the original, but works. Coincidentally, honourable mentions go to two remixes by Frozen’s original producer – William Orbit’s reworks of Justify My Love and Erotica both somehow manage to make two of her dirtiest tracks feel even sleazier.



Madonna knows her own mind, and often that mind wants to make her star in – and now direct and write – movies, which is bad news for anyone who would like Madonna to make more albums. Her Evita songs stand up, even if the best of them – Another Suitcase in Another Hall, in my view – wasn’t even supposed to be sung by her character. Unlucky, Andrea Corr. But it’s not her best movie song. Nor is I’ll Remember, which sounds like a weird mashed-up smoothie of some of her other songs. Nor is it You’ll See, which isn’t from a movie at all, it just sounds like it should be. And forget Gambler, please; Madonna certainly has. Nope, we must go back to the beginning. Her first Number 1, her best-selling single in the UK, and her finest movie moment: Into the Groove from Desperately Seeking Susan is Madonna at the height of her stubbly-armpit disco temptress phase. ‘Only when I’m dancing can I feel this free,’ she sings. And you believe her, don’t you? Wonder what she does to feel free now?


Madonna doesn’t really do flops. Borderline stiffed outside the Top 40 on its first go-round (I don’t love this song, so don’t care too much) but on rerelease at the height of her 1985 mania, it peaked at Number 2. But after that, it was hit after after hit. In the streaming era, though, post Superbowl appearance, Madge has struggled to gain a foothold on the hit parade and it’s fairly likely her Top 40 days are over. Ghosttown, off Rebel Heart, had a beautiful video with Madonna looking her very best, had Diplo on production duties, and was one of her best ballads in years. It missed the Top 100. Stupid. As Diplo said, if a younger artist had sung it, it would probably have been a hit.


It has to be one of her David Fincher numbers, surely? Slurping a saucer of milk in Express Yourself? The doomed heroine of Bad Girl? The dark and wistful Oh Father? Or the Golden Age glamour of Vogue? Or maybe Mary Lambert’s Like A Prayer with its burning crosses and sexualised saint? Or Jean-Baptiste Mondino’s Open Your Heart with aforementioned peepshow, or Justify My Love staggering between cum-drenched hotel rooms? For me? The one that would get me to set down whatever I was doing to stop and watch? The one I watched, mesmerised, a full 25 minutes of outtakes of, with Madonna messing up the dance moves and barely letting her face drop? Don’t just stand there, let’s get to it – it’s Vogue, a lookbook of Madonna’s childhood dreams. Looking at it now, with the ballroom culture that inspired the song and video more widely acknowledged and celebrated, its glossy and spotless finish feels like the antithesis of the queens who gave it their all at the balls, but their confidence and hauteur is carried through. Some of Madonna’s dancers from this video and the subsequent Blond Ambition tour were taken from the houses that participated in these balls and taught Madonna the steps, but with a 2022 lens it feels like a missed opportunity not to have featured some of the major players of the scene and maybe even taken a back seat for once. It could’ve been a life-changing moment for some of them. But hindsight is crystalline and people more qualified than me have made this case much more eloquently. And even with all that in mind, Vogue is the epitome of star power, a singer at the absolute zenith. Untouchable, immortal, free. All you need is your own imagination.


The artwork for Madonna's 1986 album True Blue, with Madonna throwing her head back

The end.

Or is it?

No, here’s one more:


Her best hairdo, for me, is Ray of Light era curls. Iconic Blond Ambition ponytail (and even the sweaty European-leg curls) a close second. Classic Madonna.

Okay, that really is it now.

Disclaimer: pitch me any of these categories tomorrow and you might get a different answer. That’s kind of how this thing works. If there is a category you’d like to see me review, drop it in the comments and I’ll do some more.

If you enjoyed this piece, consider tipping me a small amount to buy me a coffee or to help cover the site’s running costs. If you can’t, no worries, baby – we’ve all got energy bills to pay. The blog stays free.

Rich? Cool! Buy one of my books! You can find out more about those and buy them anywhere you buy your books.
Bookshop.org (which helps independent book shops)


  1. You’re wrong about “Girl Gone Wild”. Try to resist stomping to that one (the original production, not the crappy remixes) when it comes on as you’re on the dance floor. You’ll fail big time! Fun, crazy, sexy…wild!

  2. I hesitate to write this as I’m no expert, but don’t the Sondheim songs on I’m Breathless shade in to Great American Songbook territory? And could ‘Sooner or Later’ count as a soundtrack song?

    1. Haha I’d say not – they were written especially for the movie she was starring in, to be sung in character. Not the same as covering the classics. I’d say they all count as soundtrack songs, though, definitely.

  3. How about another 4 categories – best 80s, best 90s, best 00s, best 10s. I’m interested in the 00s and 10s in particular because I feel her later work rarely gets a mention, but a lot of it is bloody good.

    Great post by the way.

  4. Colabs: Love Song with Prince, surely?! Even better that the line ‘Time goes by so slowly for those who wait and those who run seem to have all the fun’ was recycled on Hung Up.

Leave a Response