Madonna’s 100 Greatest Songs (Critics’ Picks)

More silly than sultry, this enjoyably (and cartoonishly) amorous big-band swing song from the Dick Tracy companion album I’m Breathless finds Madonna melding Betty Boop and Bettie Page as she sings about how there’s “nothing like a good spanking” and her “bottom hurts just thinkin’ about it.” — JOE LYNCH

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One of two new songs on 1990’s Diamond-selling greatest hits set The Immaculate Collection, “Rescue Me” finds Madonna flipping between full-throated gospel/soul vocals and a self-effacing spoken word section, all while tension-laden synths, a bubbling bass line and a warm house beat swirl like a baptismal rainstorm. – J.L.

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Arguably the strongest pop song from Tim Rice and Andrew Lloyd Webber’s ’70s rock opera Evita, “Another Suitcase in Another Hall” was repositioned in the Alan Parker-directed ’90s film version to be sung by Madonna’s title character, rather than mistress of Juan Peron that she deposes. Good call: the delicate composition and high-register vocal make the exquisite breakup ballad a rare moment of true fragility in Madonna’s catalog, a treat to hear her play the Dionne Warwick to the composers’ Bacharach/David. — ANDREW UNTERBERGER

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A ballad about the AIDS epidemic at a time when Madonna and many others were losing friends to the disease but few were talking about it publicly. Madonna doesn’t say its name in “Spanish Eyes,” either (retitled “Pray for Spanish Eyes” on some Like a Prayer pressings), but she doesn’t really need to: the tremendous pain and confusion of its brutal impact is felt throughout her unusually strained vocal, particularly on the chorus as she pleads, “What kind of life is this?” — A.U.

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The ’40s jazz vocal standard-styled “Sooner or Later” provided Madonna the sultry ballad worthy of her double entendre-spouting femme fatale character Breathless Mahoney in 1990’s Dick Tracy, a key component of her famed Blonde Ambition era. It ended up overshadowed in pop culture by her contemporaneous “Vogue,” but it landed some esteemed hardware, winning writer Steven Sondheim the award for best original song at the 1991 Oscars. — A.U.

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A Europe-only single from the soundtrack to Madonna’s Who’s That Girl?, “The Look of Love” was not inspired by the oft-recorded ’60s pop classic of the same name, but possibly from a favorite moment of Madonna’s between James Stewart and Grace Kelly in the Hitchcock thriller Rear Window, which she described as “the most pure look of love and adoration.” The song’s aqueous production and mysterious melody give it an eerie quality befitting that inspiration, one of Madonna’s most bewitching soundtrack compositions. — A.U.

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The only new song on Madge’s 1987 remix comp You Can Dance, “Spotlight” is a lyrically simplistic affair that’s elevated by a pounding opener, sparkling keys and a charmingly earnest vocal that makes even the silliest sentiment (“Life is just a party/ That’s all you need to know”) sound like a viable philosophy for conquering the world. — J.L.

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Ray of Light, Madonna’s most introspective album, closes with the unshakably haunting, minimalist “Mer Girl.” Lonely, searching synths phase in and out while Madonna faces a life haunted by her mother’s death and her own mortality, ultimately reaching no conclusion: “I ran and I ran / I’m still running away.” — J.L.

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One of two songs performed by Madonna in the 1985 teen wrestling drama Vision Quest — hey, appearances in middling popcorn flicks is an important part of pop stardom too — “Gambler” marks the unofficial end of Madonna’s Like a Virgin era, her final jolt of gooey synth-pop before moving onto weightier fare in her True Blue era. It’s a blast, though it sounds like she could’ve tossed it off in the dressing room ten minutes earlier. — A.U.

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A post-breakup missive assuring Madonna’s ex that she’ll be just fine solo, “You’ll See” is far too seething and melodramatic for anyone to mistake it for Madge’s Gloria Gaynor moment. Even when she belts “All by myself/ I don’t need anyone at all/ I know I’ll survive” on the bridge, it mostly sounds like she’s trying to convince herself. Not much of an affirmation, but it still feels vividly real, an honest moment of self-delusion from Madonna’s best era of ballads. — A.U.

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Timbaland and Justin Timberlake recreated some of the magic they conjured with 2006’s “What Goes Around…Comes Around” for this Hard Candy deep cut, which showers the otherwise upbeat album with shadowy piano riffs and background samples of an actual storm. Madonna’s acerbic lyrics top off this quasi-ballad, warning her ex-lover about his precarious footing: “I’ve been on that ledge before/ You can’t hide yourself from me.” — BIANCA GRACIE

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With swirling, staccato strings and a leftfield spoken word section that tracks like a nursey rhyme, “God Control” found Madonna targeting America’s gun obsession in the form of an improbable gospel/disco mashup. Hailing from Madame X, which dropped the same year she turned 60, this unusual odyssey announced that Madonna was far from finished when it comes to taking risks and speaking her mind. – J.L.

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Evidently tired of trying to predict pop’s EDM-led future with their Ray of Light collaboration, Madonna and producer William Orbit teamed up again for this psych-colored ’60s flashback from the soundtrack to the Austin Powers sequel. Madonna’s still in too reflective a mindset to go full incense and peppermints with it, but she’s game enough to meet Orbit’s woozy reverb-soaked groove with one of the great smart-dumb lyrics of her career: “If I’m smart then I’ll run away/ But I’m not, so I guess I’ll stay.” — A.U.

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It’s as playful as Madonna’s been in recent years, matching a breezy beat of understated thumps and twangs with a cars-as-sex lyrical metaphor that practically mocks you for giving it any degree of additional thought. If you’re not having as much fun listening as she is going to work, you should probably be heading to a different garage anyway. — A.U.

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French DJ-producer Martin Solveig is all over Madonna’s MDNA, but weirdly, the song that most obviously apes his previous work is one he had nothing to do with: “Superstar” is a blatant copycat of Solveig’s smash Dragonette collab “Hello,” but it also has one of the sweetest, most straightforward choruses of the whole MDNA set. Ooh la la indeed. — Nolan Feeney

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It’s a testament to Madonna’s massive power in 1987 that she could release a song this lightweight from a critically drubbed film (Who’s That Girl) and still take it to No. 2 on the Hot 100. Notably, she left it off subsequent hits comps in favor of superior fare, but the arresting, thick AF bass line and the sugary determination of her delivery make this a delight, albeit a relatively slight one. — J.L.

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This one’s not from a soundtrack but maybe should’ve been: The drive and peppiness of this pop fizzer seem custom-fitted for mid-’80s montages of teen ne’er-do-wells finally starting to make good on their promise. Oh well: Madge obviously had such jams to spare in ’84, and “Over and Over” remains a pleasant surprise buried deep in both her Diamond-selling Like a Virgin album and her ’87 You Can Dance remix collection. — A.U.

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Madonna called upon Kanye West and Mike Dean to produce this downright nasty track, which is a revved up version of her seductive Erotica-era bedroom romps. This time around, she deep into her treasury of controversial Christian metaphors as she compared her, err, juices to holy water and threw in a self-referential “Vogue” sample for good measure. Only Madonna could make blasphemy taste this good. — B.G.

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The idea that anyone could neglect Madonna is almost unfathomable, but on this cut from her debut album, she’s urging her lover to keep her in mind — or else she’ll find someone who will. The refrain could apply to the song itself, really, since the bouncy synth beat and catchy lyrics are begging to be played on the radio or in the club; alas, this one wasn’t destined to be a single. — KATIE ATKINSON

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There’s so much lovely ambiguity happening in the only American Life track where Madonna goes full-on folkie. The first line of the chorus can be read as a woman turning to faith in a trying time (“Jesus Christ, will you look at me?”) or a self-owning eye-roll from someone all too aware of her need for attention (“Jesus Christ, will you look at me?”). And as she sings about trying to find her true self in a relationship, she harmonizes with different sets of lyrics, making for a clashing effect that might have you questioning which voice is the “real” Madonna — an unsettling choice, but an effective one. Has a mid-life crisis ever sounded so beautiful? — N.F.

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The opening track of Madonna’s 1994 album Bedtime Stories showed the artist was in for yet another artistic switch-up, eschewing the lush house grooves and after-hours throb of Erotica for a different kind of funk, closer to the hip-hop-steeped R&B of Janet Jackson and TLC. That’s largely due to the guitar stabs and clapping beats of the production — courtesy of the latter trio’s longtime collaborator Dallas Austin — but also due to Madonna’s ever-improving vocal assuredness, as perfectly understated (and self-aware) as ever as she insists: “Whether it’s heaven or hell/ I’m going to be living to tell.” — A.U.

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While Madonna’s movie and soundtrack version of Evita’s central ballad “Don’t Cry for Me Argentina” followed in the somber footsteps of the Andrew Lloyd Webber original, the version worked to radio in 1997 — known as the “Miami Mix” — is a weirdly enjoyable menage à trois between Broadway, Latin and club music, with a pounding beat and lively tango flourishes buoying Madonna’s earnest delivery. — J.L.

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Riding a funky New Jack Swing beat from co-writer/co-producer Andre Betts, Madonna subverts the pleading, fragile verses of this mid-Erotica cut with the addition of ominous whispering and a brassy kiss-off to her lover: “Next time you want pussy/ Just look in the mirror, baby.” — J.L.

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Madonna and writer/producer Mirwais Ahmadzaï had plenty of compelling ideas on American Life, but it took some outside help to perfect a few of them on the Remixed and Revisited EP. It’s not that the first version of “Nobody Knows Me” was soulless: For a song about identity — changing it, obscuring it, destroying it, rebuilding it — it makes sense that Madonna’s voice would be processed and Auto-Tuned into oblivion. But Mount Sims’ video-game sound effects only intensify the experience, and the extra keyboards add textures and melodies to the song that you’ll miss when you go back to the original. — N.F.

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If you were unconvinced of the sharp degree of the left turn that Madonna’s 1998 album Ray of Light would represent, one listen to “Shanti/Ashtangi” made clear that the LP meant business: a four-and-a-half minute recital of a Hindu Sanskrit prayer over a psych-dub William Orbit beat of fluttering synths and zooming guitars. Amazingly, it was sonically and melodically coherent enough to not only fit in on the album, but to actually function as something of its centerpiece, with Madonna even playing a large chunk of it as the intro to her victory-lap performance of the set’s title track at the ’98 VMAs. — A.U.

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A Beatles-esque psychedelic pop pastiche where baroque strings and George Martin-styled trumpets rub elbows with “pink elephants and lemonade,” this uncharacteristically darling entry in her catalog was an ode to frequent collaborator Patrick Leonard’s daughter. — J.L.

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It’s a sort of sonic sequel to “Beautiful Stranger,” with Madonna and Orbit returning to the tremolo’d riffs, frazzled synths and soupy drums of that single, but adding some modern flair to the electro-rock production — and a bit more blood-pumping urgency to Madonna’s vocal. It’s about another infatuation with a gorgeous mystery man, but this time the undertow proves both more sinister and more irresistible; by the time a blacked-out Madge rapturously insists “Oh, it’s amazing!,” we kinda get it already. — A.U.

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Even on her most challenging albums, Madonna tended to throw a rope to casual fans with one easily understood, highly accessible ballad. On the taboo-busting Erotica, that was “Rain,” a top 20 hit of perfectly polished R&B co-produced by Shep Pettibone. Built around one of pop music’s most timeless central lyrical images, it’s got a depth of production and vocal nuance that suggests Madonna’s spin on a great late-’80s Jimmy Jam and Terry Lewis slow jam. — A.U.

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It’s too bad Madonna relegated this Avicii collaboration for the deluxe edition of Rebel Heart. On an album with no shortage of call-backs and references to her storied career, she wrote the perfect theme song for herself: “Rebel Heart” is a sentimental sing-along that looks back on her bumpy road to stardom, adding some shrugged-off self-awareness (“I spent some time as a narcissist…trying to be so provocative/ I said, ‘Oh yeah, that was me'”) to keep things from getting too schmaltzy. — N.F.

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Replete with both a Clint Eastwood reference (“Make my day”) and audio snippets of James Cagney in raving madman mode from the 1949 gangster flick of the same name, “White Heat” is a rock-tinged dance-pop jam from True Blue‘s A-side that finds her warning/threatening a prospective lover (“My love is dangerous/ This is a bust!”), which we can only assume is how all of Madge’s relationships begin. — J.L.

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Easily the most resonant track on I’m Breathless, “Something to Remember” is more in the mold of George Michael’s “Kissing a Fool,” mixing pre-rock-era vocal-jazz influences with off-kilter contemporary production to give a particularly affecting ballad an unnerving out-of-time feel. Inspired by Madonna’s toxic marriage to actor Sean Penn, the lyrics are some of her finest, and the song set the bar so high for the singer-songwriter’s ’90s ballads that it ultimately ended up titling a 1995 compilation of her best. — A.U.

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The emotional climax of Erotica is as devastating a ballad as Madonna ever released. Like “Spanish Eyes” three years earlier, “In This Life” is an AIDS-inspired eulogy, but her grief has hardened into fury over the senseless death of her friends and the total public ignorance and lack of response to it as everyone waits “for this thing to go away.” With its menacing piano chords and mournful horns, the song’s a brutal subversion of the Beatles’ far more peaceful meditation on death a generation earlier, and Madonna’s incredulous rage as she asks “Have you ever watched your best friend die?/ Have you ever watched a grown man cry?” remains a gut-punch a quarter-century later. — A.U.

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One of two collabs with Ray of Light producer William Orbit on Madonna’s follow-up Music album, “Runaway Lover” opens with pulsating, uncertain synths before a relentless beat kicks in and swiftly snowballs. The lyrics might be confounding (“It doesn’t pay to give away what you lack/ And never get your money back” — huh?) but this high-octane track shows Veronica Electronica could rave when she felt like it. — J.L.

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Another American Life cut that got a superior overhaul via the Remixed & Revisited EP, “Love Profusion” in its original form was half state-of-the-world protest song, half love song. But it feels a little flat in comparison to this supercharged, hard-rock-inspired take, which swaps out acoustic guitars and 808s for electric guitars and hissing live drums, upgrading Madonna’s complaints and questions about the nature of humanity into a fierce, anxious battle cry. — N.F.

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What began as an original Erotica composition entitled “Goodbye to Innocence” eventually morphed into a cover of the Peggy Lee-popularized pop standard “Fever”. But while most versions of this classic smolder, Madonna gets distant and detached, delivering an icy club banger that sounds less like a torch song from yesteryear and more like a soundtrack for anonymous encounters that would make Ms. Lee blush. — J.L.

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At the height of the trip-hop’s international pull, U.K. collective Massive Attack were hooked up with Madonna (via mutual producer Nellee Hooper) to contribute to a ’95 Gaye tribute compilation. The resulting cover collab was the perfect mix of the former’s grinding beats and lush strings with the latter’s mid-’90s cool, reflective sensuality, which Madonna was pleased enough with to use as the opener to her Something to Remember compilation that year. The two artists nearly met back up three years later for what eventually became a signature hit for Massive Attack, “Teardrop” — how it might’ve sounded with Madonna instead of Liz Fraser on vocals remains one of ’90s pop’s great what-ifs. — A.U.

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After a historic run of 16 consecutive top five singles, Madonna’s seemingly unstoppable winning streak was finally interrupted by “Oh Father,” an orchestral, melodramatic waltz about the singer-songwriter’s fraught relationship with her dad. The song’s relative lack of chart success — it peaked at No. 20 — was unsurprising given the weighty subject matter, but the single not only set the tone for Madonna’s more contemplative, downtempo decade to come, it also provided an early model for the piano-led power balladry of ’90s singer-songwriters like Tori Amos and Jewel. — A.U.

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Melding glitchy techno with acoustic folk is a bold move for any pop star, particularly for an album’s lead single. If that wasn’t enough, Madonna also throws in a full-on rap to her American Life title track, where she rhymes “latte” with “shot-ay.” It’s bizarre, ballsy and not entirely a creative homerun — and it left radio audiences cold in 2003, barely peaking inside the Hot 100’s top 40. Yet it’s easily one of the most fascinating detours in pop-diva history, and when taken as kitsch, the rap is strangely magnetic. — J.L.

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Try to quiz your pop fan friends to name Madonna’s 12 Hot 100 No. 1s, and the one they’ll most likely blank on is “Who’s That Girl?,” a hit single from the screwball comedy bust of the same name. The flick’s soundtrack, featuring four new Madge songs, was obviously more of a success, and the title track expanded on the Spanglish hook and Latin-flavored pop bounce of “La Isla Bonita” with a similarly contagious chorus and sparkling production from Madonna and Patrick Leonard. All artists should be so lucky to have this as the least of their many No. 1s. — A.U.

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As far as proper studio albums go, Ray of Light is famously Madonna’s vocal showcase: For 1996’s movie-musical Evita, the singer underwent extensive vocal training, and she was reportedly so thrilled by what she accomplished in her lessons that she used to leave her friends voicemails of herself singing to show them what her body could do. On Ray of Light‘s fourth single, you can hear that practice in action with the airy trill she deploys at the end of every line, lending an earth-goddess vibe to William Orbit’s sidewinding instrumentation. It’s a no-punches-pulled song about endings, but it feels like a beginning. — N.F.

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Combining the deep house and dissonant sounds of Erotica with a cheeky, filtered vocal that wouldn’t have sounded out of place on the Dick Tracy companion LP I’m Breathless, “Bye Bye Baby” was only ever released as a single outside of North America, but it remains one of the oddball highlights on the most ambitious album in her catalog. — J.L.

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An ebullient ode to then-boo Sean Penn, “True Blue” melds doo-wop harmonies with a quaint ‘80s beat. By all reasonable measures, it should be disposable pop fluff; but in Madonna’s hands, it’s an impossibly charming slice of puppy love — albeit a naive one, something she herself later acknowledged, admitting in 2015: “I didn’t know what I was talking about when I wrote it.”  — J.L.

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One of only a handful of feature appearances Madonna has made over her career, “Me Against the Music” remains a deeply weird collab between two of the biggest pop stars of the last half-century. It’s an alternately competitive, seductive and schizophrenic duet, with a frenetic energy and muddled structure — not to mention the most Neptunes-like beat that Pharrell never actually touched. It made no sense as a lead single (in front of “Toxic,” no less!), but it remains an endlessly fascinating experiment 15 years later, a symbolic passing of the torch that left both hands partially singed. — A.U.

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Kenneth “Babyface” Edmonds left his fingerprints all over “Forbidden Love,” from the romantic whispered vocals to the quiet storm-influenced production, making this Bedtime ballad one of Madonna’s most soulful tracks to date. Its steamy vibe leaves you in a trance as Madonna entices you with lyrical charmers like “What’s wrong is why it feels so right / I want to feel your sweet caress.” Whew, it’s getting hot in here… — B.G.

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This easy, breezy trifle from Bedtime Stories is all about keeping things movin’ and groovin’, so it makes sense that the track is propelled by a groovy, carefree bass line. The perpetually laid-back Slick Rick probably appreciates the kindred song’s “La Di Da Di” shout-out. — K.A.

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No need to check the liner notes: Prince’s musical fingerprints are all over this one, from his sky-high falsetto to his funky guitar. “Love Song” is a jam, obviously, but it remains most notable for pairing two iconic artists and peers at the top of their respective games, especially at a time when A-list features were far less frequent than they are today. — K.A.

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While the intense “Above & Beyond Remix” better suits its infamously violent music video, it’s the mid-paced album version of “What It Feels Like For a Girl” that endures. The single serves as a delicate yet firm protest against the patriarchy, complete with a spoken word segment from Charlotte Gainsbourg (via the 1993 drama The Cement Garden) and devastating societal critiques in her lyrics (“When you open up your mouth to speak, could you be a little weak?”). — J.L.

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Madonna took us straight to the disco dance floor with “Beat Goes On,” which calls for feather boas, extravagant jewelry and a champagne flute in hand. The Neptunes’ production keeps the euphoric high going with shimmering bells and handclaps, while Kanye West puts on his finest tux (“Just flew in from Paris, voulez-vous?”) for one of his funkiest guest verses. — B.G.

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One of the most musically ambitious tracks of Madonna’s 1990s, “Sky Fits Heaven” blends trance throb with drum n bass propulsion, ambient atmsopherics and even some light rock shredding for a strikingly buoyant soundscape. Madge’s Max Blagg-inspired lyrical meditations occasionally border on the impenetrable, but the chorus lifts even higher than expected with an easily comprehended refrain that practically registers as career-defining: “I think I’ll follow my heart/ It’s a very good place to start.” — A.U.

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Madonna’s final great bubblegum pop song of the ’80s — and maybe ever, since its innocence would prove understandably hard to recapture in the decades to come. “Cherish” was a beach-ready update to the Association’s ’60s chart-topper that viewed her love in the simplest terms possible: “Romeo and Juliet, they never felt this way I bet.” Madonna’s said that it was written “in a super-hyper-positive state of mind that I knew was not going to last,” and her determination to not let that impending inevitability show up in a single synth-horn on “Cherish” made it so resilient to cynicism in the decades since. — A.U.

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Madonna pretty much set the gold standard for dance-pop anthems with gospel choirs when she first got down on her knees back to take us there in 1989, but the first single from Rebel Heart is a similarly worthy entrant in that tradition. If the extra voices joining in on the uplifting “I’m gonna carry on” hook doesn’t put some pep in your step, a thundering house beat courtesy of Diplo and Ariel Rechtshaid (with Alicia Keys on piano!) certainly will. — N.F.

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An emotional lyrical rendering from Madonna — and an absolutely gorgeous synthscape courtesy of her and co-producer Patrick Leonard — elevates what could’ve otherwise been a pat soundtrack single (from the absurd ’90s college dramedy With Honors) to one of her great one-offs. Its No. 2 peak on the Hot 100 after an underwhelming Erotica chart run could’ve portended an unfortunate return to staid respectability for Madonna in the mid-’90s, but luckily she was back to weird-ass electro-pop experimentation within a couple of singles. — A.U.

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With a tension-filled synth opener that nods to Pet Shop Boys’ “West End Girls” and lyrics that harken back to her own “Keep It Together,” “Jump” is a propulsive, disco drum-indebted club track about resilience, self-sufficiency and the need to risk everything to achieve anything. Think of it as the closest thing to a Madonna Manifesto on wax. — J.L.

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From the start, Hard Candy was never going to be Madonna’s most original album. There’s no reason she couldn’t team up with hip-hop heavyweights like Timbaland and Pharrell, but she’d have to share their arsenal of spacey sounds with everyone else who’d hit the studio with them before her. Yet it’s no big surprise that the presence of a titan like Madonna inspired her collaborators to step their games up, and this marching-band-inspired stomper was certainly a cut above everything else Timbo was cooking up by 2008. Madonna and co-star Justin Timberlake keep the apocalyptic talk light and fun, but even she can’t help trying to actually save the world by slipping some advice about how “the road to hell is paved with good intentions” into the second verse. — N.F.

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At some point in our lives, we’ve all been met with metaphorical waves crashing into our lives, representing lessons designed to test our strength. With “Swim,” Madonna was wading between a spiritual awakening (due to a newfound interest in Kabbalah), adjusting to motherhood, and a particularly shocking tragedy: The singer-songwriter learned about the death of her close friend and esteemed designer Gianni Versace while recording “Swim,” which gives it even more of a chilling feel. — B.G.

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While detractors derided her “Minnie Mouse on helium” voice on songs like “Physical Attraction” from her 1983 self-titled debut, the critics failed to get what the club kids and suburban mallrats instinctively understood — this ain’t meant to be a set of vocal tour de forces from a showy pro. With libidinous synths, hypnotic beats, airy vocals and a chirping vocal delivery, “Physical Attraction” is — like the lyrics suggest — about turning your brain off for a moment and giving yourself over to absolute pleasure. — J.L.

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Madonna’s collaboration with Icelandic alt-pop legend Björk was a bizarre choice for a third single off 1994’s Bedtime Stories. Its lightly flickering beat and moaning synths were pitched at a very radio-unfriendly midtempo minimalism, and Björk’s anti-lyric about eschewing words (rallied around the refrain “Let’s get unconscious, honey”) hardly rated as Madonna’s most rousing. The song’s core pulse held some allure, however, and longtime remixer Junior Vasquez drew it out with his far more maximal Wet Dream Remix, which found the implicit hedonism in the song’s hook — and determined that it need not have to choose between the bedroom and the dance floor after all. — A.U.

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This dreamy-eyed single — written, in true ’80s fashion, for the Matthew Modine wrestling drama Vision Quest — marked a couple of firsts for Madonna: her first Grammy nomination (for best female pop vocal performance) and her first hit ballad. That sonic shift, perfect for young fans desperate for a slow song to come on so they could get closer to their partner, foretold the versatility to come from the pop star. – K.A.

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It’s hard to imagine anyone pulling off a musically upbeat dance-pop song about a crumbling marriage and domestic abuse, but Madonna had reached a level of nuance and maturity on the Like a Prayer album that’s rarely been equaled in modern pop music. Her robotic rundown of the symptoms of a toxic relationship toward the song’s close is a harrowing, emotionally inverse precursor to her rapped list of Hollywood legends on “Vogue” just a year later. — J.L.

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A year before Debbie Gibson and Tiffany essentially set the gold standard for America-conquering mall-pop, Madonna buried the blueprint in the middle of her True Blue album with “Where’s the Party?” The then-27-year-old’s effervescent tribute to post-workweek revelry acknowledges a necessary impending maturity — “Guess I’m one of the grown-ups/ Now I have to get the job done,” she sighs in the second verse — but through sheer force of dance-pop will it ensures that the carefree good times will last for at least one more song. The key to the song is the little snarl that she packs into each “Where’s the party??” demand, making it clear that there’ll be hell to pay for failure to divulge any pertinent info. — A.U.

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While most of the songs on Erotica explore the explicit and often rewarding aspects of sex, “Bad Girl” takes a different route, tackling the emotional consequences that can come with the act. You can almost hear Madonna try to mask tears as her cracked voice tells the tale of a woman who attempts to find love through tendless one-night stands and drunken late nights on the town. It’s a sharp lesson that pain can be synonymous with passion. — B.G.

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The tightest of Madonna’s collaborations with superproducers The Neptunes on her underrated Hard Candy album, “She’s Not Me” is a disco throwback with a deadly groove and a wicked sense of humor, which even provides its own 12-inch remix with an outro that dissolves into Auto-Tuned 21st-century clubbiness. The song’s strut (partly courtesy of The Revolution’s Wendy Melvoin on acoustic guitar) and winkingly paranoid lyric provide all the juice the song really needed, but it got an extra spark anyway when Madge played it as part of her mash-up of “Express Yourself” and Lady Gaga’s “Born This Way” on 2012’s MDNA tour — inspiring some educated speculation about who’d most recently been freaking Madonna out by dressing like her and talking like her. — A.U.

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Madonna’s first-ever single set the tone for much of her catalog to come, persuading club-goers to lose themselves to dance and kick-starting the theme of inclusivity that is still central to her message today: There is no separation of class, gender, race, sexuality or any other label when everybody is sweating it out together on the dance floor. — K.A.

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As the second track on the Music album, “Impressive Instant” makes clear that Madonna and French electro producer Mirwais were fearlessly weird while working in tandem in the early 21st century. On the growling electro-pop jam, the duo brew up a dizzying cauldron of bubbling techno and syncopated rhythms that resist traditional production tropes and leave you feeling dizzy, invigorated and entranced all at once. — J.L.

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Rebel Heart tapped into a secret weapon few of Madonna’s competitor-peers possess: longevity. What other superstar could flex their icon status and name-check themselves in a chorus and still have it feel completely earned? With its otherworldly and aggressive progressive production from Diplo and SOPHIE (is it supposed to sound like a dog barking at 3:30?), “Bitch I’m Madonna” is a bonkers soundtrack for the nights you feel like the star of your own house party — and a reminder that there’s really no one else on the queen of pop’s level. — N.F.

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The lead single of Madonna’s Bedtime Stories era saw her continuing to pivot away from the R-rated club excursions of Erotica into a more restrained R&B sound — but one that still felt layered and unmistakably adult. “Secret” was accessible without giving the whole game away, building its chorus around haunting harmonies borrowed from Nirvana’s “Something in the Way” and a lyrical conceit that buries a smile underneath its mystery. It’s a song about intimacy disguised as a song about betrayal, and it showed that Madonna could rebound from the bad press of the Erotica era without reverting to playing it safe. — A.U.

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It takes Ciccone cajones to rhyme “New York” with “dork,” but if there’s one thing clear about Confessions-era Madonna, it’s that she’s completely past giving a fuck. The pounding post-disco “I Love New York” is the rare ode to the Big Apple that drops the “City of Dreams” sugarcoating and embraces NYC in all its dirty, loud and difficult glory. It’s impossible to imagine any other pop queen getting away with a line like “New York is not for little pussies who scream,” and that’s exactly why the world has been talking about Madonna for 35 years and counting. — J.L.

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Certainly the most innocent-sounding song to nonetheless earn inclusion on Tipper Gore and the PMRC’s infamous 1985 “Filthy Fifteen” list of the current pop songs they found to be most objectionable, “Dress You Up” arguably borders on adult content with its repeated “all over your body” exhortations but stays PG at worst with its generally over-caffeinated exuberance. With a knockout chorus, infectious synth line and some exceptionally placed “Owww” backing vocals, the fact that “Dress You Up” was only the fourth-best single to be pulled from Like a Virgin suggested what a force to be reckoned with Madonna would remain for the rest of the millennium. — A.U.

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Who else besides Madonna has the power to transform a scathing diss targeted for an ex-lover into one of the best and most empowering dance hits of the ’00s? “Sorry,” co-produced by British electronic mastermind Stuart Price, starts off with calm, ballad-esque strings, but soon the pounding drums and ‘80s-inspired synths kick things into overdrive. Madonna made the song’s message easily accessible for fans around the world, uttering versions of “I’m sorry” and “Forgive me” in nine different languages. — B.G.

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The first single from Ray of Light took the previous album’s “Secret” to an even more sweeping place of emotional balladry, with drums that appeared and swelled unpredictably; cinematic strings worthy of previous collaborator Björk; and synths that throbbed threateningly below the production’s icy surface. The lyrics again concerned intimacy, but this time they were a plea to her partner to open up, with the chorus no longer content with all the secrets her baby was keeping. It one-upped the Bedtime Stories lead single in most areas, including on the Hot 100 — where “Secret” peaked at No. 3, “Frozen” quickly bound to No. 2. — A.U.

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No song better married the experimental impulses of American Life with her more accessible pop sensibilities like this topsy-turvy electro-romp, which simultaneously romanticized dreams of Tinseltown stardom while also calling out their emptiness. (Of course a song about the phoniness of the entertainment industry would soundtrack her infamous stunt at the ’03 VMAs.) By once again messing with her vocals via studio wizardry and pitch-shifting, she and Mirwais turned the song into the kind of disorienting funhouse mirror she’s singing about. — N.F.

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Overshadowed by album-mates “Like a Virgin” and “Material Girl,” “Angel” is a sadly undervalued gem from her second album. As Madonna slips from lovestruck coo to sultry contralto, producer Nile Rodgers peppers in sprightly guitar and wry giggles from the star herself. The ineffably charming dance-pop lark also features some of Madge’s cutest come-ons: “I can’t hear the traffic rushing by/ Just the pounding of my heart and that’s why/ You must be an angel.” — J.L.

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The lyrics to this True Blue Hot 100-topper, of course, started a firestorm for the lightning-rod pop star when it came out in 1986, with critics unfairly accusing her of glamorizing teen pregnancy and typically anti-Madonna conservatives praising what they saw as the song’s pro-life message. But the real melodrama was in the music, with dramatic, staccato strings accompanying a driving dance beat that perfectly matched the urgency of the song’s pleading message. — K.A.

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Despite its most famous quote being about crying, you wouldn’t necessarily think of 1992 baseball dramedy (and all-time what’s-on-TBS-today classic) A League of Their Own as a tearjerker — until you remember “This Used to Be My Playground.” A decade and a half before Don Draper rhapsodized about nostalgia being “pain from an old wound,” Madonna’s melodramatic League theme ably demonstrated the inherent knife-twisting in looking back, with a lifetime’s worth of hurt in each lyrical memory: “Because life is short/ And before you know/ You’re feeling old/ And your heart is breaking.” Robert Smith never wrote a song anywhere near this merciless; somehow it became Madonna’s tenth No. 1 hit in August 1992. — A.U.

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Few can sing about desire deferred and sound so damn exuberant while doing it, but Madonna provides a masterclass in how it’s done on the defiant “Open Your Heart,” which explodes with a infectious vibrancy from the twinkling synths at the start and carries through to the joyous, you-couldn’t-get-rid-of-me-if-you-wanted-to chorus. “Nothing can stop me from triumph,” she vowed on the 1987 No. 1 — and honestly, nothing ever did. — J.L.

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A half-decade before “Blurred Lines,” The Neptunes granted Madonna a very similar bass-and-cowbell shuffle for her finest Hard Candy single. Madonna matches the relentless groove with lyrics of Terminator-like resilience and proficiency (“Don’t stop me now, don’t need to catch my breath/ I can go on and on and on”), as the synths around her just get meaner and meaner. The song stiffed on the charts at the time, peaking at No. 57, but today it sounds impossibly winning, like a flashback to an alternate-universe version of Madonna’s early career where she got together with Arthur Russell and made a a bunch of classic weirdo club-slayers for the NY underground. — A.U.

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Hearing society’s richest and most powerful people talk about how nothing really matters and how love is all you need can be hard to view any way but skeptically, but by the time she was nearing 40, Madonna had probably seen more than most of us experience in our entire lifetimes. On this fourth single from Ray of Light, she keeps the platitudes from sounding empty by taking her younger self to task: “Nothing really mattered to me/ but making myself happy….I lived so selfishly.” Dance music is often a tool for artists and listeners to build their identities; here, Madonna uses pulsing beats to shed her skin. — N.F.

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The epic beat (courtesy of Stuart Price) on this Confessions highlight recalls ’90s dance gems like Stardust’s “Music Sounds Better With You” while simultaneously setting up the mainstream EDM boom still to come. In the lyrics, meanwhile, Madonna returns to the theme of finding common ground and/or love on the dance floor, acknowledging that love at first sight is an “illusion” but not really caring if it’s real or not, as long as both parties believe it is. — K.A.

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Opening with vinyl static, a loin-tingling bassline and an eerie sample of Kool and the Gang’s “Jungle Boogie,” “Erotica” arrived as the boldest, riskiest reinvention in a career full of them. An icy declaration (via alter ego Dita Parlo) that it was time to kick open the doors on kinks and own them without shame made plenty of prudes bristle in 1992. But years of dirrty followers have proven that not only was Madonna fingering a chord that was already deep within our collective unconscious, but few can do it better than M when it comes to getting raw without pandering or risking exploitation. — J.L.

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One of Madonna’s biggest early hits — and the one most despised by the singer herself. Never mind that exuberant chorus that rolls through its vowels like a rollercoaster cresting before a drop, or the call-and-response moments that make for a karaoke enthusiast’s dream: Madonna remains unequivocal. “My least favorite song [of mine] is ‘Material Girl,’” she wrote in 2015. “I never, ever want to hear it again!” For decades, she’s bristled at the idea of coming across as a vapid, riches-obsessed celebrity because of the song’s dual function as a media nickname. But if you take the song not quite so literally, you get a portrait of Madonna even she would probably agree is on-brand: A woman who knows what she wants and doesn’t tolerate bullshit on her path to getting it. — N.F.

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Madonna has worn plenty of hats in her career, and for the Music era she literally decided to grab her best Stetson and become a full-blown cowgirl. “Don’t Tell Me,” the album’s second single, fused this new country-rock direction with elements of dance and trip-hop. A mix of poetically off-center lyrics like “Tell the bed not to lay/ Like the open mouth of a grave,” a CD-skip stutter effect and that jangly guitar riff, “Tell Me” would’ve ended up a mess for many artists. But for Madonna, it landed her yet another top five Hot 100 hit. — B.G.

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Written solely by late Miles Davis sideman Reggie Lucas, it’s easy to see how “Borderline” became the nascent New York star’s first top ten hit on the Hot 100 — it’s pure pop bliss about that timeless topic, losing your cool over a crush. But while the track might’ve been a hit for anyone, it’s Madonna’s vocal — an overpowering mixture of aching naivete and teasing vitality — that pushes “Borderline” into the rarefied realm of pop classics that continue to sound fresh and relevant to every passing generation. — J.L.

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“Crazy for You” was a fine love song, but “Live to Tell” is the first truly great Madonna ballad: a shellshocked emotional odyssey of shame, trauma and resilience, with the psychological complexity and sonic density of a Songs From the Big Chair single. The devastating truth at the core of “Live to Tell” is never revealed, but also “never far behind,” the knowledge leaving Madonna both empowered and paralyzed. But as captivating as the lyrics are, the song’s most affecting moment is its pre-bridge dissolve, where only the dramatic waves of synth remain, a moment of seeming crisis (or revelation) before a fragile Madonna gently reintroduces herself to the melody: “If I ran away… I’d never have the strength to go very far.” — A.U.

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For a pop star defined by her ferocious confidence, “Drowned World/Substitute for Love” showed us that after conquering the world, Madonna still had doubts about the value of fame, money and everything she’d worked so relentless toward. But while the ambient desert soundscape conveys her internal emptiness, the message skips over self-pity and moves directly into self-examination, brilliantly setting the tone for Madonna’s most spiritually satisfying album — and one of the most emotionally intelligent landmark LPs in pop history. — J.L.

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This irresistible dance hit is a nightclub nursery rhyme, taking the children’s poem “Star Light, Star Bright” and flipping it into a sexy Studio 54 come-on about heavenly bodies. Madonna is credited as the sole songwriter on the track, so she gets full credit for taking advantage of the rote simplicity of a nursery rhyme and turning it into a radio-ready earworm, with a music video that created the first of many iconic looks for the burgeoning superstar. — K.A.

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Madonna’s career has been too mutli-faceted to reduce to a simple two-word message, but “Express Yourself” would probably be a pretty good start: From her “Material Girl” days to her Rebel Heart era, self-expression, and the need to identify what you want and then go out and get it, has always been paramount. Here, the sentiment is backed by a five-star chorus and full-bodied dance-pop groove, unifying and satisfying enough to be worthy of its Sly & The Family Stone inspiration, as well as a David Fincher-directed, peak-MTV music video that was a next-level production even for ’80s Madonna. Speaking of that clip, when you’re grabbing “Express Yourself” for party playlists, make sure you pass over the overcooked Like a Prayer version for the much tighter video edit, found on the Celebration compilation.  — A.U.

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More than two decades before Madonna gave us a questionable “Spanish Lesson,” the then-rising icon experimented with Latin influences for the first time with “La Isla Bonita.” One of the most romantic songs in her catalog, the True Blue single blended maracas, conga drums and Spanish guitar that immediately drifts you to the fictionalized paradise island. But the best part of “La Isla Bonita” is Madonna’s mature, lush vocals, which were a stunning departure from the “helium” register previously made famous on “Like A Virgin” and “Lucky Star.” — B.G.

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Madonna’s only No. 1 single of the 21st century is so simple, it almost seems hastily written: “Music! Makes the people! Come together….Yeah!” Yeah? That’s all? But the unfussy spirit works, if only because it’s not hard to imagine Madonna in the eye of the dance floor, throwing down to Mirwais’s glitchy disco, having too much fun to think of anything deeper or more complex. The music video starring Sacha Baron Cohen as his Ali G. character may have ended up dated by now, but few Madonna singles have sound this fresh almost 20 years out. — N.F.

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Madonna’s famously banned video and ensuing Erotica/Sex era may have you remembering “Justify My Love” as more pornographic than it actually is. In reality, the dirtiest part of the song is the drum loop, a smoked-out, bass-bombed James Brown-via-Public Enemy shuffle that suggests all kind of nocturnal activities — expanded upon only lightly by Madonna’s lyrics (taken from a poem by former Prince protege Ingrid Chavez), whose calls for emotional intimacy are more provocative than any carnal fantasy described. But just because it’s not explicitly NC-17 doesn’t mean the song’s eroticism isn’t still palpable and formidable — few moments in pop history are as sexually charged as the chorus, where everything drops out but Madonna (“Wanting. Needing. WAITING.”) and that incessant drum loop, adorned only by a ghostly harmony on the song’s beguiling insistence: “For you.To justify my love.” — A.U.

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No early ‘80s pop album was complete without one song that threw a scorching rock riff into the synth-dance mix, and on her self-titled debut, that was the irrepressible “Burning Up.” Even this early in her career, Madonna pulls off the deft trick of singing about submission without sacrificing one iota of agency. When she snarls “Unlike the others I’ll do anything — I’m not the same, I have no shame, I’m on fire,” she sounds less like a doormat and more like a pioneer of female Big Dick Energy in pop. — J.L.

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Great pop songs build a refrain around a clever, instantly unforgettable lyric like “Like a virgin/ Touched for the very first time,” but all-time pop songs throw an ecstatic “HEY!” in the middle just to make sure. Such was the level of expertise on display when Madonna hooked up with writers Tom Kelly and Billy Steinberg and producer Nile Rodgers for her first Hot 100 No. 1, and one of the defining songs of the 1980s. “Like a Virgin” has become such a part of the pop vernacular that we take the million little things it does brilliantly for granted, from the unexpected chord changes of its verses to its tantalizingly protracted outro (“Can’t you hear my heart beat… For the very first time?“), providing an absolute masterclass in ’80s pop songcraft and making Madonna’s superstardom permanently undeniable. — A.U.

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A stylistic diversion on the often chilly Erotica album, “Deeper and Deeper” calls back to “Vogue” (both musically and via a direct late-song lift) with its disco warmth and propulsive house beat. But while “Vogue” was about the joy of release, “Deeper and Deeper” is a dance anthem for those who haven’t yet reached that level of confidence. Oozing pent-up desire after years of suppression, it builds to an inescapable climax (punctuated by Spanish guitar and castanets) drenched in the exhilarating danger of taking those first few timid steps toward whatever freedoms you’ve been denying yourself. — J.L.

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Madonna was a big enough star in the ’90s that an album like Bedtime Stories could go multi-Platinum and spawn a seven-week Hot 100 No. 1 and still be considered something of a disappointment. That long-running chart-topper was “Take a Bow,” which sort of provided the fulcrum for Madonna’s pop decade: an R&B slow jam accessible enough to crossover just about everywhere, but rich and personal enough to still feel urgent. The lachrymose crawl of “Bow” almost makes it too much to handle, but the tender vocal interplay between Madonna and co-writer/producer Babyface is as captivating a tango as the one between bull and fighter in the VH1-conquering video. The song became iconic enough that Rihanna could borrow its skeleton for her own breakup ballad a decade later, without needing to make the callback any more explicit than its title. — A.U.

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You could check into a hotel in your own town for a short staycation, but wouldn’t it be cheaper to just go to the club instead? Madonna preaches the power of dance to escape from everyday worries, borrowing the British variant of holiday for her first mainstream American hit and marking her maiden voyage to the Hot 100 top 20. It turned out that one of her most carefree singles is what quickly made top 40 radio care about her, starting a fixation that would last for a stunning 33 consecutive top 40 hits from there. — K.A.

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Years before pop’s EDM boom, Madonna was already connecting the sounds of night clubs past with electronic music’s future on 2005’s disco-inspired Confessions on a Dance Floor LP. Taking on source material as iconic as ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight)” was no easy task — and not just because Madonna had to write a letter to the band’s Benny Andersson and Björn Ulvaeus, famously picky about sample usage, asking for permission to use it. But Madonna (with help from producer Stuart Price and his galloping synths) made it her own — so successfully, in fact, that when Cher unveiled her modern cover of “Gimme!” earlier this month, many on social media joked that she’d sampled “Hung Up.” — N.F.

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Bedtime Stories was Madonna’s way of winning back naysayers following the Erotica backlash, but she still made it clear she wasn’t going to apologize for perceived past transgressions. With the help of go-to ’90s producer Dave Hall (Mary J. Blige, Mariah Carey), “Human Nature” — the last of the album’s four singles — used saucy R&B and a searing sample from rap group Main Source to fuel its theme of liberation.

“Human Nature” drips with sarcasm as Madonna mockingly professes, “Oops, I didn’t know I couldn’t talk about sex” — a statement brilliantly punctuated by the sound of slamming doors. The song’s confrontational nature carried on through the video, where Madonna is seen both tied up and rocking latex dominatrix gear, using bondage as a metaphor for the constriction of her artistic and sexual freedom. The feminist message of “Human Nature” would later be carried on by women who have proudly taken influence from the icon’s handbook, from Britney Spears (who performed the song with Madonna in 2008) to Rihanna’s (who employed similar imagery for “S&M”). — B.G.

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It shouldn’t work, really: Madonna adapting a 1971 folk tune and turning into a raving adrenaline-fest that sounds like what you’d probably hear if you took a Hyperloop train to the center of the sun in the year 3018. But just go with it — that’s Madonna does. Why exactly is she addressing a zephyr in the sky at night? Is getting home from work a cause for celebration or an admission of defeat? Who cares! There’s a reason Madonna doesn’t finish her sentence half the time when she wails “And I fe-el…” The title track of her 1998 LP is a pure jolt of feeling, whatever form that takes. — N.F.

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Madonna always kept her ear to the underground, and in 1990 she married Harlem ball culture (with help from dancers/choreographers Jose Gutierez Xtravaganza and Luis Xtravaganza) to the relatively nascent genre of house music (with longtime ally Shep Pettibone co-writing and co-producing) to give the world “Vogue.” A Hot 100 topper for three weeks in 1990, “Vogue” is quintessential Ciccone: The lyrics hit on her recurrent themes of escaping the pains of life that you know (life that you knooooow) through dance floor ecstasy and her adulation of Golden Era Hollywood glam (the black-and-white David Fincher-directed video is arguably her finest visual moment) — all while an endlessly listenable, strangely of-its-era-yet-timeless disco-house anthem plays. You might try to resist, but once it starts playing, you have no choice but to let your body go with the flow. — J.L.

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Religious iconography has been a key part of Madonna’s image since she wore a rosary dangling above her “Boy Toy” belt buckle at the 1984 VMAs. (Or, really, since her name was first scribed on her birth certificate.) She perfectly delivers on that borderline-blasphemous blend of pop culture and her Roman Catholic upbringing on the title track of 1989’s Like a Prayer, equating love to a transcendent religious awakening. One of the main reasons the lyrics work so well is that she could be singing about a monogamous relationship, a powerful sexual connection, a platonic loved one, or even God him (or her) self — it all comes back to love. Of course, the song’s full religious experience would be incomplete without a perfectly deployed gospel choir, humming hushed harmonies over the verses and singing full-throated sermons to drive it all home. Life might be a mystery, but the mastery of this song is irrefutable. — K.A.

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“And you can dance/ For inspiration” 

Madonna was inspired to write “Into the Groove” by a combination of her love for the dance floor and an infatuation with a Latin boy from around her Lower East Side apartment. “When I was writing it, I was sitting in a fourth-floor walk-up in Avenue B,” she recalled to Details in 1994, “and there was this gorgeous Puerto Rican boy sitting across from me that I wanted to go out on a date with, and I just wanted to get it over with.” In that same interview, she reveals (much to the reporter’s horror) that “Into the Groove” is a song she’d rather never perform again, calling it “dorky.” “You’ve never really understood how good that song was, have you?” the interviewer asks, aware that even if the artist has tired of the song over the years, no one else has. Madonna shrugs. 

“Only when I’m dancing can I feel this free/ At night, I lock the door where no one else can see”

She’s not wrong about “Into the Groove” being dorky. Despite having already set new standards for boldness in pop music by the time of its release via her 1985 big-screen debut Desperately Seeking Susan, the song’s greatest lyric is conspicuously shy, with Madonna slinking back to her place to literally dance like nobody’s watching. But that timid couplet — half of the greatest pre-chorus ever written — ends up being as empowering as anything Madonna ever wrote. It’s a love letter to her millions of fans who’ll never be stars anywhere outside of their bedroom mirrors, a revelation that even the Queen of Pop still finds dancing on her own to be life’s greatest, truest thrill. And anyway, she’s not planning on swaying solo forever, going onto proclaim “I’m tired of dancing here all by myself/ Tonight, I’m gonna dance with someone else.” By the time of the bridge, it’s mission accomplished: “Touch my body, move in time/ Now I know you’re mine.” 

“Music can be such a revelation/ Dancing around you feel the sweet sensation” 

Madonna’s desire to be rid of “Groove” belies the fact that it wasn’t supposed to be hers to begin with — the song was originally written and recorded as a demo for Cheyne, a protege of her ex Mark Kamins, before Madonna reclaimed it as her own. Apologies to Cheyne, for whom the single could’ve been a career-maker, but “Groove” always had to be a Madonna song: No other artist in pop history has understood as well that the lines that separate music, dancing, sex and love into discrete entities are tenuous at best, and in “Into the Groove,” all four elements are continuously smashing into each other, becoming virtually interchangeable over the song’s timeless synth shimmer and jack-hammering bass. Over the years, she may have lost the love for “Groove,” but not for what it stands for, not for what a revelation music and dance and sex and love can still be after 60 years. That’s Madonna. And you better come on, ‘coz she’s still waiting. — A.U.

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