Madonna. Madge. Mistress Dita. The queen of Pop. The queen of working out. The queen of wearing sunglasses indoors and sporting grills on your teeth that make you borderline unintelligible. However you see Madonna, you’ll have a favourite – and probably least favourite – incarnation. Her catalogue is enormous, comprising sexy songs and sad songs, political songs and nonsensical songs, and songs that continue to scandalise the clean-living and respectable among us.
Picking the best is nigh-impossible, but we’ve tried to. As she prepares to unveil her 15th studio album Confessions II – a sequel to her 2005 disco masterpiece Confessions on a Dancefloor – we’ve ranked her top 45 songs released so far, one for each year she’s been releasing music.
Your faves might be missing, entire albums could be absent (don’t shoot me, Rebel Heart stans!), but it speaks to the sheer brilliance of Madonna herself. She’s an icon, she’s a legend, and she is – then, now and for always – the moment.
45. “Die Another Day”
open image in galleryMadonna’s 2002 Bond theme was thoroughly rinsed upon release, because everything Madonna does tends to be subject to annoying over-criticism. I sort of get it with this one, though. “Die Another Day” is, as is typical of the woman behind it, an act of total domination: this isn’t a 007 song by Madonna, but a Madonna song shoved into a 007 movie, take it or leave it. There are the ingredients of the franchise’s sounds here and there – in the dramatic strings and audible moaning – along with things altogether her own, from the distorted vocals to the unabashed camp. “Sigmund Freud… analyse this!” she demands ? at one point, because why not?
44. “Supernatural”
Yes, this is a track in which Madonna has sex with a ghost. Like the theme song to a horny version of Ghostbusters, Madonna is spooked in the night by a randy spectre, then starts to worry she’s fallen pregnant by him (“a ghost baby?” she queries). This 1989 number is knowingly ludicrous, Madonna giggling as she boasts that she’s going to take off her pants in preparation for her lover’s “super-duper-naturally big thing” – it’s a rare Madonna track laced with overt humour, alongside the requisite funky bassline.
43. “Time Stood Still”
The only saving grace to Madonna’s ill-fated 2000 gay/straight parenting comedy with Rupert Everett, The Next Best Thing, is this pretty love song, which appears on its soundtrack. Madonna’s vocal is pristine, serenaded by the twinkly piano flutters of William Orbit, her main collaborator from this era.
42. “I’m Addicted”
We don’t like to talk about 2012’s MDNA, the only Madonna album that could arguably be described as half-arsed. Led by a collaboration with future Trumpian agitators Nicki Minaj and MIA that’s aged like milk, MDNA only really has one good track on it, with Madonna otherwise largely checked out and busy with her Wallis Simpson movie WE (it was a rough time for her fandom, to be honest). And that song is “I’m Addicted”, its absolute hurricane of furious synthesizer noises best experienced at max volume.
41. “Papa Don’t Preach”
open image in galleryA curious mix of the classically operatic yet thematically contemporary, this is Madonna’s original anti-patriarchy, pro-choice, “controversy? yes please!” bop. Released in 1986, it’s about a teenage girl who’s keeping her baby, goddammit, no matter what her hectoring father says. If it feels a little anonymous (Madonna doesn’t typically sing as characters, does she?), it’s because she didn’t have a huge amount of involvement with its lyrics. It’s difficult to deny its cultural staying power, though.
40. “Easy Ride”
A folky detour on her divisive 2003 record American Life, this essentially works as Madonna’s life manifesto. “I want the good life / But I don’t want an easy ride,” she sings. “What I want is to work for it / Feel the blood and sweat on my fingertips.” It’s brilliantly sparse and dramatic, and wildly underrated.
39. “I Feel So Free”
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open image in galleryIt’s a bit early to determine this a Madonna classic, considering it’s brand new and the lead off her new album, Confessions II. But doesn’t it feel bloody huge? We meet Madonna as she narrates her loneliness, her fear of strangers, but the salvation she feels on the dancefloor. Stuart Price’s production is straight out of the Giorgio Moroder playbook, with slivers of “I Feel Love” and lots of cosmic, sexy melancholy throbbing through it.
38. “Lucky Star”
open image in galleryEarly Madonna! Her vocals are adorably squeaky on this very early 1983 single, as she sings of a lover with the naivety of a woman barely out of her teens, but with enough carnal longing to gesture to the rampant boundary-pusher she’ll soon become. “Shine your heavenly body tonight,” she pleads. A star was born.
37. “Bedtime Story”
open image in galleryA rare collaboration between Madonna and kooky Icelandic genius Björk, 1994’s “Bedtime Story” gloops along like a jittery dream, Madonna’s vocal a hushed quiver, Nellee Hooper’s production full of plush ambience and longing. It’s so wavy. And “Let’s get unconscious, honey” is up there with some of the most plainly evocative lyrics ever, surely?
36. “I’ll Remember”
open image in galleryDesigned as a palette cleanser on the heels of both her Sex photo book and flop (but camp!) erotic thriller Body of Evidence, 1994’s “I’ll Remember” is radically un-sexy by design. The sonic equivalent of a knitted cardigan, it is driven by an echo-y bass line, while Madonna softly hums and recalls an old love affair. She’d rip up this kind of MOR niceness within a year or two, but that doesn’t mean this isn’t still quietly brilliant.
35. “Hollywood”
open image in galleryAn electro-folk banger from American Life, “Hollywood” conjures images of Norma Desmond and rampant fame-whoring, as Madonna laments the empty excesses of Los Angeles and the dire nature of celebrity. “Trip the station, change the channel,” she roars. She also kissed Britney Spears at the MTV VMAs while singing this so, you know, yes.
34. “Crazy for You”
open image in galleryA true-blue Eighties torch song and Madonna’s attempt at her own “‘Take My Breath Away’ on the Top Gun soundtrack” moment… albeit for the now almost entirely forgotten 1985 romantic drama Vision Quest. But gosh is it wonderful, mainly because of the production, which is full of sweeping strings and big, lush background vocals.
33. “Secret”
open image in galleryWe mentioned it a few entries ago, but Madonna is just really, really good at humming, and it’s the secret sauce here – the lead single off 1994’s trippy, R&B-influenced Bedtime Stories. It quickly conjures a fierce, sensual groove, as Madonna boasts of a lover with a dark side. It’s arguable she’s never been cooler.
32. “Music”
open image in galleryIs it sacrilege to rank this at 33? “Music”, from 2000, is obviously one of Madonna’s signature hits, and of course absolutely bangs. But between Ali G being all over the video, the neo-funk of Mirwais Ahmadzaï’s production and the spacey distortion on Madonna’s vocals, it feels very, very Y2K, whereas so much more from her discography feels incredibly timeless. Still, you have to respect the brilliance here all the same.
31. “Burning Up”
open image in galleryIt’s interesting to look back on Madonna’s second ever single – how it seems to sit directly at the centre of the thrashing post-punk club world she was emerging from at the time, and the sparkly new wave pop she’d completely transcend, then dominate, just a year or two later. “Burning Up”, released in 1983, is therefore a bit of a tease of what was to come: the energy, the double entendres, the sheer command of Madonna’s vocal. It was clear she was no ordinary pop star, even at this point.
30. “Candy Perfume Girl”
An underrated Madonna album track, sporting the same languorous sensuality of the softer singles on her breathtaking 1998 record Ray of Light (namely “Frozen” and “The Power of Good-Bye”), but with an incredibly grungy production backing her up. It’s a little Shirley Manson, a little Sneaker Pimps. It’s Madonna dipping her toe into the sparse trip-hop pop sound of the late Nineties, and completely owning it.
29. “Secret Garden”
Arguably the most thinking-outside-of-the-box song in Madonna’s discography, “Secret Garden” is the last randy gasp on the tracklist of 1992’s Erotica, her vocals low and croaky, like it was sung at the end of a long night. She’s swaddled in the sounds of a jazz club – shuffling drums, the gorgeous flutter of piano. And yes, duh, it’s about her vagina. But when wasn’t Madonna singing about her vagina in 1992?
28. “Future Lovers”
One of the secret masterpieces on 2005’s Confessions on a Dancefloor is this phenomenal mash-up of spoken word, synthesizers and orgiastic moans. It would make Donna Summer proud. Producer Stuart Price twists and distorts the single line “in the evidence of its brilliance” until it resembles a nonsensical tongue-twister, like the sonic equivalent of tripping balls in front of laser lights.
27. “American Life”
open image in galleryLike “Die Another Day”, this was released at a time when treating Madonna like a punching bag became incredibly popular for Britain’s tabloids. That she started speaking in a cut-glass English accent around this period didn’t help her much. But it means much of her music from the early Noughties, and her 2003 record American Life in particular, got an unfair drubbing. This lead single is fascinatingly blunt in its lyricism – Madonna is pissed, furious at the Bush administration and cultural imperialism, and does a kitsch but also sort of sensational rap halfway through that’s actually aged pretty well. I, too, will drink a soy latte (with a double shot-tay) in tribute.
26. “La Isla Bonita”
open image in galleryGloriously melodramatic in ways that in hindsight feel sort of unusual for Madonna, who’s only on occasion trafficked in this sort of thing. Lyrically, this 1986 single is very mystical-exotic-island-by-numbers, Madonna dreaming of a faraway Spanish locale populated by the beautiful. But it’s undeniably just very fun, full of maracas and flamenco guitar and OTT crooning.
25. “God Control”
open image in galleryYou might have noticed already that this is a ranking devoid of much of Madonna’s newer material, which is less to do with the quality of her recent albums, and more to do with how much better they work as bodies of work rather than as albums that can be stripped for parts – Madame X, released in 2019, is case in point: it’s an experimental, enjoyably odd little mess of a thing, albeit with only one song that feels as if it could stand alone alongside Madge classics. And that’s “God Control”, a six-minute odyssey about mass shootings and discrimination (it was inspired by the Pulse nightclub shooting in 2016, in which 49 people were murdered), which funnels disco, a gospel choir and sounds of gunshots. Madonna sings of rage, hopelessness and watching the world and feeling as if you’re going insane. It’s completely brilliant, and completely devastating.
24. “What It Feels Like For a Girl”
open image in galleryDesperately sad, glitchy folk-pop made in the afterglow of Ray of Light, this mournful single off of Music opens with a monologue by Charlotte Gainsborough (ripped from the 1994 film The Cement Garden) and only grows more transcendent from there. The less said about the Guy Ritchie-directed video – set to a remix and depicting Madonna committing vehicular murder-suicide with an elderly woman – the better… maybe. It was a weird time.
23. “Sorry”
open image in galleryThe grumpy little sister of “Hung Up”, “Sorry” is acidic where that song is euphoric, playing like the messy comedown after a night out. Like much of Confessions on a Dancefloor, it hinges on the perfect symbiosis between Madonna and producer Stuart Price, who twists and contorts her vocals with abandon, and swaddles her in reverb and blissful synth noise.
22. “Oh Father”
open image in galleryA key touchstone in the canon of daddy issues anthems, and inspired by Madonna’s complicated relationship with her father, 1989’s “Oh Father” is all surging violins and pleading vocals. It flopped at the time, but has aged brilliantly.
21. “The Power of Good-Bye”
open image in galleryMadonna and producer William Orbit just found one another at the right time – Madonna a new mother, tangling with maturity and religion and the uncertainty of being 15 years in the pop game, and Orbit mastering a sound that felt digital and sparse and altogether lonely. “The Power of Good-Bye”, a single from 1998, is one of their greatest collaborations, Madonna singing of leaving a lover behind, while computer blips and strings engulf her.
20. “Thief of Hearts”
Appearing on 1992’s Erotica, this is one of Madonna’s angriest songs (it opens with a smash of glass and Madonna snarling “Bitch!”), but is sung with the languor of someone by now used to being romantically disappointed. Before, that is, the incredibly fizzy bridge you may have seen on TikTok recently: “You’ll do it, you’ll take it / You’ll screw it, you’ll fake it…”
19. “Into the Groove”
open image in galleryMadonna’s first UK number one, and the song you could argue properly announced her as the queen of pop. But (whisper it), she does basically this exact same track a bit better later down the line. That doesn’t mean this isn’t masterful, though. The synth hook of this 1985 song is irresistibly danceable, and there’s something so thrilling about Madonna’s vocals on that bridge: “Now I know you’re mine!!”
18. “Justify My Love”
open image in galleryThe video for “Justify My Love” was banned for being just too damn raunchy, accelerating Madonna’s fame and notoriety to even higher heights back in 1990. The noise was justified though: this is too randy, too unlike anything else at the time and even arguably today. There’s little coyness here, just Madonna monologuing about getting freaky between the sheets against a hypnotic drum beat. “Talk to me / Tell me your dreams / Am I in them?” Yes.
17. “Live to Tell”
open image in galleryBoth because it’s the theme song to his 1986 movie At Close Range, and the fact that Madonna was in a turbulent relationship with him during its recording, this has Sean Penn all over it – “Live to Tell” is one of Madonna’s finest ballads, ambiguous in its themes, but undeniably evocative. Is it about domestic violence? Betrayal? Pure survival? She’s never disclosed it. The production – sharp, moody, very Eighties – is marvellous, though, particularly how it drops into near-silence four minutes in, then explodes back into life.
16. “Material Girl”
open image in galleryMadonna at her squeakiest, 1985’s “Material Girl” is glorious Eighties excess, and either a feminist triumph or a vapid bit of capitalist propaganda (choose your fighter!). The best Madonna songs tend to be divisive, after all. And that production! The plastic-y wind tunnel effect, those chunky synths. And that video! Madonna in full Marilyn Monroe garb, toying with an army of silly boys. She’s the best who’ll ever do it.
15. “Open Your Heart”
open image in gallery“Watch out!” Gosh, the drums go hard in this 1987 banger, which opens loud and never lets up. It sparkles, and there’s so much fun to be had in Madonna – imperial phase fully activated – just insisting no one can, or will, resist her.
14. “Beautiful Stranger”
open image in galleryAbsolutely inescapable in 1999 was Madonna’s theme song for Austin Powers 2, which carries over producer William Orbit from Ray of Light. The result is this fantastically psychedelic number, which is a bit The Doors, a bit jangle-pop, and impossible not to sing along to.
13. “Drowned World/Substitute for Love”
open image in galleryThere’s so much breathing room to this five-minute baring of Madonna’s soul, that kicks off 1998’s Ray of Light, and which recaps her career up till then. “I had so many lovers / Who’ve settled for the thrill / Basking in my spotlight / I never felt so happy.” And then, as she sings of nascent motherhood, producer William Orbit ditches the bloopy ambience for psychedelic electric guitar and that trademark Madonna humming again. It’s miraculous.
12. “Like a Virgin”
open image in galleryIn 1984, “Like a Virgin” sent Madonna stratospheric, launching her second album and breaking the brains of anyone who watched her on MTV, rolling around in a wedding dress and flashing her underwear. It’s essentially the blueprint for everything that came after it, by Madonna and every other pop girlie in her wake: naughty, provocative, indulgent, and thrillingly fun. A karaoke classic that’s somehow never grown cringe.
11. “Erotica”
open image in galleryTwo years after “Justify My Love”, 1992’s “Erotica” was also banned from MTV, arriving as a second detour into Madonna’s sexual fantasies. It’s more full-bodied than “Justify My Love”, in that its production is full of freaky sonic pivots, from that recurring, swirly “Jungle Boogie” sample to the Arabic hymn towards the end. It’s also so refreshing, particularly when listened to in 2026, to hear a song about sex that treats the subject matter with absolute sincerity. There’s no silliness here, just Madonna in total dominatrix mode, enjoying the moment and demanding you get on board with her.
10. “Don’t Tell Me”
open image in galleryThe finest four minutes made by Madonna and her early Y2K collaborator, producer Mirwais Ahmadzaï, 2000’s “Don’t Tell Me” is a hazy blur of country folk and electronic futurism. Madonna’s vocals, and the production around her, are relentlessly cut up and halted, like someone’s attacked the track with scissors. It’s arguably Madonna at her most defiant – as if you didn’t know it by now, never try and tell her what to do.
9. “Frozen”
open image in galleryIt’s sort of baffling that this expansive, ambient and decidedly non-commercial electronic ballad from 1998 was as big as it was – could you imagine anyone dominating the charts with something like “Frozen” today? Putting that aside, this remains staggering – it’s a little mystical, a little tribal, and very, very dramatic.
8. “Deeper and Deeper”
open image in galleryAn exercise in total, blissful abandon in a night club, 1992’s “Deeper and Deeper” is a peak Madonna party anthem. It’s also majestically arranged – you think you’ve got the hang of it, then it suddenly pivots to an extended flamenco bridge, then back to throbbing disco dazzle.
7. “Rain”
open image in galleryDoesn’t “Rain” just sound expensive? This epic ballad off the Erotica album is only horny if you squint a little. Then again, with its hesitant build and flowing water crescendo, could it actually be its most horny single? Either way, it’s a Madonna all-timer, with those violent strings and the gorgeous moment where she recites two monologues at once, her words colliding with one another like crashing waves. Symbolism!
6. “Express Yourself”
open image in galleryThe video to this 1989 track, directed by her then-frequent collaborator David Fincher, is a mini-movie in itself, and somehow looks more expensive than everything Marvel has produced in the last decade combined. There are skyscrapers, massive dance routines, dozens of extras, costume changes, practical sets, a cat. And the song itself feels like a total celebration of everything Madonna embodied at that point: total autonomy, total authority, total global dominance.
5. “Like a Prayer”
open image in galleryIf not the greatest Madonna song, 1989’s “Like a Prayer” is certainly her most important. Between the track itself and its controversy-stoking video, its collision of themes – sex, religion, race – speak to the unique greatness of Madonna herself, and how she’s always been able to tackle big ideas in commercial packages. That “Like a Prayer” got her ad campaign for Pepsi axed – an act of censorship that somehow made her even more famous – and she got to keep the $5m Pepsi had already paid her, is case in point.
4. “Bad Girl”
open image in galleryAnd speaking of David Fincher videos, there’s this one, too – a miniature erotic thriller that has the baroque stylings of his Se7en, made a few years later, and starring Christopher Walken as the Angel of Death. Obviously, it’s a masterpiece. Don’t overlook the song, though. Released in 1992, it’s Madonna’s greatest ballad, and a haunting depiction of depression, melancholy and big-city loneliness. No other Madonna song sounds like it, or matches its blend of luxury and devastation.
3. “Hung Up”
open image in galleryIt’s 2005, 23 years into her career, and Madonna unveils this, a thrilling, chugging disco masterpiece based around that transcendent Abba sample. She just gets it, doesn’t she? The sing-along simplicity of the central hook (“Every little thing that you say or do / I’m hung up”), the rise and fall of Stuart Price’s production, how it bends and curls and then ascends again. Stunning.
2. “Ray of Light”
open image in galleryThere’s a famous clip of Madonna performing “Ray of Light” on Oprah Winfrey’s talk show in 1998, like a nocturnal raver bringing the party to a book club, and every single person in the vicinity losing their damn minds. Winfrey is gyrating all over the place, at the centre of a sea of middle-aged mums leaping up and down in unison. Little else sums up the power of this song, which careens between soft electric guitar and euphoric acid house synths, leaving absolutely nothing on the table. It almost sounds holy, as if Jesus swallowed a pill and saw the entirety of the universe before him, then started shooting laser beams out of his eyes.
1. “Vogue”
open image in galleryIt sort of had to be, surely? Intended as the B-side to a largely forgotten single called “Keep It Together”, then shunted onto the end of Madonna’s soundtrack to the wacky Warren Beatty vanity project Dick Tracy, 1990’s “Vogue” would ultimately prove to be everything majestic, commanding and breathtaking about Madonna as an artist. This is a blancmange of pure gay, an exhilarating tribute to nightclubbing, glamour and the queer underground. It’s all there instantly – those fruity little synth stabs, those glorious finger-snaps, Madonna’s vocals somewhere between nurturing den mother and mouthy dominatrix. You can’t not move to it, bow to it, want to strut and thrust and sing along to it. What an absolute masterpiece, one that’s forever imitated but never, ever bettered. Imagine dying in the early days of 1990 and never once getting to hear it. It’s unthinkable, isn’t it?