The 100 Greatest Madonna Songs

The premiere of Madonna’s video for “Give Me All Your Luvin,'” the first single off her new album M.D.N.A., is today, children. It’s bound to be a little over-the-top and nutty, like the deranged song itself, and I assume it’s not going to live up to the greatest stuff in Madonna’s catalog. Then I remember: What does live up to the best stuff in Madonna’s catalog? Turns out, not much. Madonna’s repertoire is a varied and thundering collection of self-empowering pop ditties, soulful ballads, and kooky little anomalies. And they’re mostly all irreplaceable. In the tradition of Rolling Stone, who listed their 100 Greatest Beatles Songs a couple years ago, let’s reinspect Madonna’s complete history and name her definitive 100 jams. Ready? Start disagreeing NOW.

100. “Dance 2Night” from Hard Candy

Hard Candy’s most euphoric groove (and best dancefloor-filler) makes the stilted duo of Madge and Justin Timberlake seem like a proper dancefloor romance.

99. “Can’t Stop” from the Who’s That Girl? Soundtrack

Nobody croons about insatiability like Madonna, and this lesser-known track from the filmic milestone Who’s That Girl? was no doubt a help in winning over Griffin Dunne.

98. “You Must Love Me” from the Evita soundtrack

It’s an Oscar-winning ballad, but “You Must Love Me” is more notable as a showcase, paradoxically, both for Madonna’s headmasterly chill and surprising vulnerability.

97. “4 Minutes” from Hard Candy

While Madonna has enjoyed duets with more fitting partners, her collaboration with Justin Timberlake yielded this bumping, boinging precursor to Armageddon.

96. “I Love New York” from Confessions on a Dance Floor

The lyrics? Dorky. The street-tough grit? Contrived. But somehow Madonna’s renewed Danceteria chutzpah sells this piece of glitzed-out camp. It’s the Sex and the City 2 of Madonna songs – unforgivable, yet undeniably fun.

95. “Bye Bye Baby” from Erotica

A candidate for the frostiest song on Erotica, “Bye Bye Baby” is a hip-hop kiss-off with cabaret flair. And it made for a hell of a VMA performance.

94. “Nothing Really Matters” from Ray of Light

Copping both new-age maxims and Beatle sentiments (“Everything I give you all comes back to me”), “Nothing Really Matters” is as queer and curious as a red patent-leather geisha costume.

93. “Shoo-Bee-Doo” from Like A Virgin

“Shoo-bee-doo-bee-doo, baby!” should not work as a triumphant chorus, but Madonna delivers it with such a fierce, preteen urgency that its nonsense melodrama is downright moving.

92. “Super Pop” from Confessions on a Dance Floor, Bonus Track

Madonna’s megalomania is at peak insanity here, but she’s pretty damn provocative and nervy about it. After mysteriously namedropping Isaac Newton and Martin Luther, she throws down a few interesting and hilarious proclamations. My favorite: “If I was a song, I would be ‘Super Pop.’” Sounds like a decent epitaph from here.

91. “Love Profusion” from American Life

Cryptic though it may be to listeners, “Love Profusion” sounds like a moment of sweet clarity to its singer. When you start referencing Cole Porter lyrics (“I’ve got you under my skin”), you must be pretty stoked.

90. “True Blue” from True Blue

The title track off Madonna’s most celebratory album is a cutesy tribute to girl groups with one hell of a romantic swell. Her Annie-esque call of “The sun is bursting right out of the sky” hopefully melted Sean Penn a bit.

89. “Intervention” from American Life

If American Life had been an EP featuring the four-song sequence from “Love Profusion” to “Intervention,” I could possibly give it a sterling recommendation. As such, “Intervention” is a lovely anomaly on that misfired album in its hopeful and unpretentious message.

88. “How High” from Confessions on a Dance Floor

Madonna set out to make electronic music more accessible and cerebral on Ray of Light, and she continues in that tradition on Confessions’ “How High.” Her pulsing interrogations about fame, fulfillment, and meaning here are compelling and articulate.

87. “Jimmy, Jimmy” from True Blue

After her toast to James Cagney on “White Heat,” Madonna’s silly ode to a dangerous lover named Jimmy feels like an overjoyed bit of fan-fiction. But don’t we all want a man who cradles us in one arm while brandishing a tommy gun in the other.

86. “Why’s It So Hard” from Erotica

Like most great Madonna albums, Erotica features a plea for understanding and world unity deep into its second half. “Why’s It So Hard” is both trite and deeply sincere, and it’s always refreshing to hear Madonna – a middle child if ever one existed – call out to her “brothers and sisters.”


85. “Sky Fits Heaven” from Ray of Light

Ray of Light may be a touch too self-serious, but “Sky Fits Heaven” features a heartfelt and straightforward introspection that wouldn’t feel out of place on a more confessional (and lyric-driven) album from ’98 like The Miseducation of Lauryn Hill.

84. “One More Chance” from Something to Remember

Something to Remember is an essential purchase for casual Madonna fans, as it validates her standing as a kickass balladeer and moving vocalist. “One More Chance” is nothing more than a guitar and Madonna’s torch-song trilling, and it’s more effective than anything you’ve heard out of Taylor Swift’s mouth in the past five years.

83. “I Deserve It” from Music

Sandwiched between Music’s flashy, danceable “Runaway Lover” and “Amazing,” the quavery “I Deserve It” feels like an unassuming and nervous testament to her then-new marriage to Guy Ritchie. Just like her unassuming and nervous guitar-playing on Letterman that same year, her efforts here are endearing.

82. “Nobody Knows Me” from American Life

The throbbing electronics and sheer tunefulness of this track put it heads and tails above most American Life fare, but Madonna’s bitchy elitism (“I don’t watch TV!”) qualify it as the album’s brassiest jam.

81. “Like a Virgin” from Like a Virgin

Your eyes do not deceive you: While “Like a Virgin” made for a thrilling cultural moment and an unforgettable VMA performance, it’s also the Madonna single that has perhaps aged worst and most since its debut. It’s kitschy and fun, but it’s also the one Madonna tune no one ever has to hear again. Still: You hump that gondola, girl.

80. “Amazing” from Music

The thumping, harrumphing rodeo clowning of Music peaks in “Amazing,” with all its gushy romantic pains thrashing about like neon paints on an inner-city mural. Credit must be paid to producer Mirwais, who makes this bouncy soundscape almost incessantly colorful.

79. “Bad Girl” from Erotica

Homos know it most, but I’ll reiterate for Madonna novices: Erotica is about heart. This classy ballad with a great message is a parable about a woman who’s sick of walking on the wild side.

78. “The Power of Goodbye” from Ray of Light

Several memorable things here: 1) The video, in which a ravishing Madonna plays chess with the eternally studly Goran Visnjic, 2) the earth-mother vocals, and 3) some of the best lyrics of Madonna’s career. My favorite: “You were my lesson I had to learn / I was your fortress you had to burn.”

77. “Think of Me” from Madonna

We’re already getting to the point in the list where I want to caption everything with “I effing love this song.” Well, get this: “Think of Me” is a lovable plea for sexual consideration in the vein of Teena Marie and Lisa Lisa. You can’t argue with early Madonna. She’s too damn real.

76. “Ain’t No Big Deal” from Pre-Madonna

Madonna’s obnoxious chipmunk squeals are irresistible in this bopping rarity. It so smacks of her NY urchin days that you can almost hear her chomping popcorn for dinner.

75. “Nobody’s Perfect” from Music

Though Music is a bundle of gay weirdness, “Nobody’s Perfect” sticks out as exceptionally bizarre. It’s a self-lacerating, whining meditation that manages to be beautiful. I doubt you’ll hear one of Madonna’s upcoming M.D.N.A. tracks cry anything as melancholic as, “What did you expect? I’m doing my best.”

74. “Nothing Fails” from American Life

“I’m not religious, but I feel such love” is one Ecstasy-blitzed Donna Summer shoutout, but Madonna couches her euphoric musings in a gospel chorus and sweeping electronics. Moving indeed, Madge.

73. “Where’s the Party?” from True Blue

Though it’s a minor moment of jubilance on an album chockablock with joy, “Where’s the Party” is such a fun-loving, twinkly bit of girly urgency. It’s effect on the viewer is threefold: you smile, you skip, you werq.

72. “Santa Baby” from A Very Special Christmas

Madonna replaces Eartha Kitt’s feline comeliness with coquettish babytalk, and the result is a Christmas treasure. I giggle every time she gets to, “I don’t mean on the phone.”

71. “Swim” from Ray of Light

Here you have it: a sign that Madonna may have her feet planted in this world. Like an ethereal, patrician version of Marvin Gaye, she croons the headlines: “Children killing children while the students rape their teachers / Comets fly across the sky while the churches burn their preachers.” It’s heavy and heavy-handed, but it’s also fitting for Ray of Light’s fixation on consciousness.

70. “Get Together” from Confessions on a Dance Floor

Madonna pitched “Get Together” as a nonstop remix, and here we have what sounds like a burgeoning romance tucked within the black lights of a fabulous club. It’s as free-associative and cerebral as anything Madonna’s released since ’98, but this time she’s sporting a sly sexuality.

69. “Jump” from Confessions on a Dance Floor

“Jump” concerns Madonna’s primary draw: her choice to accept her self-consciousness, own it, and choose fearlessness anyway. It’s her strongest power anthem of the 2000s.

68. “More” from I’m Breathless

Sondheim! This Broadway-world update to “Material Girl” has our bratty chanteuse chirping for the one thing she doesn’t have: more. Cole Porter would be proud of the wicked wordplay that Madonna so gamely spews.

67. “Pray for Spanish Eyes” from Like A Prayer

One of the saddest songs on the list, Madonna’s bleating ode to a fallen friend is a devastating vigil. We needed a music video to this one.

66. “White Heat” from True Blue

Not only is “White Heat” a slick and unabashed tribute to Jimmy Cagney, but Madonna is clearly torqued to revel in the classic Hollywood whizzbang. Her love is dangerous!

65. “Celebration” from Celebration

Madonna’s double-disc greatest hits needed a better cap than “Hey You” (chills), so she spit out this rollicking dance jam as a perfect companion piece to that other testament to celebration, “Holiday.”


64. “Cherish” from Like A Prayer

It’s schmaltzy and perky, but “Cherish” may also be Madonna’s cheeriest song ever. It’s the kind of glee that makes a man of deep artistic insight like Herb Ritts cut subtext and shoot a video about mermaids.

63. “Don’t Stop” from Bedtime Stories

Production on Bedtime Stories was a mess; the sheer amount of producers in the edit bay made for a hodgepodge of an album (with tons of unreleased B-sides), but “Don’t Stop” stands as one of Madonna’s slinkiest, classiest slow jams.

62. “Die Another Day” from American Life

The highest-ranking song on this list from Madonna’s most egregiously pretentious album is hard-edged, clunky, and cool: The shoutout to Sigmund Freud is cheeky, her empowered numbness is fierce, and the lyrics cut like an epee worthy of James Bond’s fencing instructor.

61. “Who’s That Girl?” from the Who’s That Girl? soundtrack

In 1986, Madonna just wanted to be Spanish, dammit. Though she’d give us a more timeless tune in that vein, “Who’s That Girl?” is still a sexy little tribute to those minxes you just can’t catch up with.

60. “Runaway Lover” from Music

And speaking of minxes you can’t keep up with: Madonna’s on the losing end of a strained romance here, and she bubbles with contempt like a stiffed bartender at a decadent disco saloon. Curse those urban cowboys!

59. “Something to Remember” from I’m Breathless

I’ll continue to tout Madonna’s skills as a balladeer, but who could deliver a line like, “I hear you still say ‘Love yourself’” with as much visceral hurt?

58. “I’d Rather Be Your Lover” from Bedtime Stories

This sinister Oedipal ode matches Madonna’s girl-group coos with the sultry rhymes of her Maverick signee Me’Shell NdegeOcello, who gets a verse to herself and dishes sass, according to the liner notes, “on bass and in yo’ face.”

57. “Fever” from Erotica

Madonna isn’t known for her covers, but her languid, moaned treatment of the Peggy Lee standard made it positively libidinous – all through the night.

56. “Gone” from Music

The haunting closer to Music is damn dark: “Turn to stone / Lose my faith / I’ll be gone before it happens.” And underplayed! Mirwais knows all the tricks.

55. “Sidewalk Talk” from Jellybean’s Wotupski!?!

Now, this isn’t a proper Madonna song, but the young and plucky vixen owns Jellybean’s chart hit the minute she’s heard on the record. “Watch where you walk / ‘cause the sidewalks talk” is one of the sassiest things Madonna’s ever uttered – and you’ll be delighted to know she wrote the entire record herself (at least according to the liner notes).

54. “Justify My Love” from The Immaculate Collection

Madonna had always loved sex, but she’d never been clinically serious about the topic until “Justify My Love,” the carnal, churning Public Enemy riff about sexual fantasy and salacious reciprocation. Her exploration of the forbidden was made naughtier by MTV’s well-publicized video ban.

53. “Sooner Or Later” from I’m Breathless

Call me a turncoat, but I just don’t like Evita or Madonna’s involvement with it. I do, however, like her as Breathless Mahoney – particularly when she’s owning the nightclub intimacy of Stephen Sondheim’s Oscar-winning “Sooner or Later.” It’s satisfying to believe a singer who coos, “Baby, you’re mine on a platter.”

52. “This Used to Be My Playground” from Something to Remember

The theme to Madonna’s best movie (hands down!) A League of Their Own is nostalgic and sweet, and it gave her a major hit that utilized the lachrymose qualities in her voice – the same qualities that went underappreciated on her minor hit “Oh Father.”

51. “Words” from Erotica

What begins as an elementary complaint about verbal abuse (“I don’t want to hear your words”) evolves into beat poetry about the importance of articulation. “Don’t mince words, don’t be evasive / Speak your mind, be persuasive,” she deadpans, once again clarifying that Erotica was about personal convictions, not just carnality.

50. “Forbidden Love” (’05) from Confessions on a Dance Floor

Madonna claimed COADF was for the gays, and this song about proves it. “Are we supposed to be together?” the song chimes in a stifled, male-robot voice, and the implications of underground (if not “downlow”) serendipity are startlingly apparent and gorgeously sonic.

49. “Bedtime Story” from Bedtime Stories

Bjork could’ve saved this odyssey of unconsciousness for herself, but she finds a worthy dreamer in Madonna, who despairs in her alienation. While “Words” touted wordiness, “Bedtime Story” dismisses verbiage as fruitless noise: “Words are useless, especially sentences… How can they explain how I feel?”

48. “You’ll See” from Something to Remember

Sure, she’s still hung up on the matador from the “Take a Bow” video in “You’ll See,” but Madonna’s declaration of independence over beautiful Spanish guitar-playing is organic and inspired. “It takes more strength to cry, admit defeat” she warns, challenging both her paramour and herself to the task.

47. “Rain” from Erotica

Yes, “love coming down like rain” could be a nasty image, but Madonna makes it palatable and sensual, surprising us with a sauna-warm ballad soon after the chilly beats of Erotica’s preceding tracks.

46. “Keep It Together” from Like a Prayer

Though perhaps more notable for housing “Vogue” as a B-side on its single, “Keep It Together” is a rollicking family reunion that served as the perfect concluding performance in Truth Or Dare. It’s the sunny side of “Oh Father’s” grim familial reckoning.

45. “What It Feels Like For a Girl” from Music

On an album filled with potential hits, “What It Feels Like for a Girl” was an obvious single. Its tenderness and power resonated like no Madonna ballad since “Take a Bow,” which is why it was shocking – and fabulous – that its video was such a violent display of rage, recklessness, and grand theft.

44. “Waiting” from Erotica

You can sum up “Waiting’s” disgraced longing with its awesome, beat-driven refrain at song’s end: “I knew it from the start that you would desert me / You’re gonna break my heart, baby please don’t hurt me.” Fin.


43. “Gambler” from the Vision Quest soundtrack

Madonna wails on us with riverboat chutzpah in this springy ditty. How is this the only Madonna jam to climax with the line, “You can’t stop me now”?

42. “I Want You” from Something to Remember

I hope if Madonna has any regrets about her career, one of them is never again collaborating with the wizards of Massive Attack, who make her cover of Marvin Gaye’s “I Want You” an affecting, somewhat spooky listening experience. And I’m calling it right now: This is the most underrated video in the Madonna oeuvre.

41. “Drowned World/Substitute For Love” from Ray of Light

The opening notes of Ray of Light indicate we’re not in for the typical jiving and rejoicing of Madonna’s previous albums. In fact, the party seems over: “No ferris wheel / no party steal / no laughter in the dark / no one-night stand / no far-off land / no fire that I can spark.” It’s a bloodletting, but it marks one of Madonna’s finest accomplishments as a songwriter.

40. “Sanctuary” from Bedtime Stories

The problem with Hard Candy was that Madonna let her producers take over, but that’s exactly the genius of “Sanctuary.” Though Madonna’s ethereal vocal serves the song well, it’s producer Dallas Austin’s heavenly soundscape that steals the show.

39. “Oh Father” from Like a Prayer

While Like a Prayer was a critical triumph for other reasons, “Oh Father” stands as its quintessential moment of confessional wisdom. Its dredged-up childhood traumas serve as the flipside to “Dear Jessie’s” childlike optimism, and Madonna gives one of her most searing vocal performances to date.

38. “Dress You Up” from Like a Virgin

Silly and a little scandalous, “Dress You Up” is pep upon pep upon pep. It’s perfect. It’s all over your body.

37. “Physical Attraction” from Madonna

“Physical Attraction” is six minutes and 40 seconds of romantic chemistry, poppy hooks, and one tremendous idea: “Maybe we were meant to be together / even though we’ve never met before.”

36. “Beautiful Stranger” from the Austin Powers: The Spy Who Shagged Me soundtrack

It’s always a thrill when we remember that Madonna is totally funny. When she rubs her ass in a dreaming Austin Powers’ face, she’s giving us comic gold, and get this: the song is a roaring success too. William Orbit’s psychedelic stylings suit Madonna’s groovy wistfulness perfectly.

35. “Holiday” from Madonna

Come together in every nation, because there’s this chick on American Bandstand who says she wants to “rule the world”, and I believe her.

34. “Forbidden Love” (’94) from Bedtime Stories

The deep, sweltering R&B groove here feels like a scalding hot shower that Herb Ritts would’ve enjoyed filming. Madonna also shifts from “sexy” to “revealing” midway through the song, admitting in a lovely hush, “Rejection is the greatest aphrodisiac.”

33. “I Know It” from Madonna

It’s still so cool to listen to Madonna’s first album and here the bossy, bratty, vulnerable, steely conviction that will act as a through-line in her gigantic career. “I Know It” is whiny power pop, and its girl-group bravado is delicious. Madonna’s delivery of “I know you think I’m the foolish one” is confrontational and almost defeated, and it’s one of the great endearing moments in her early career.

32. “Hung Up” from Confessions on a Dance Floor

Thank ABBA for penning the fabulous “Gimme! Gimme! Gimme! (A Man After Midnight),” because its galloping beat fuels the salacious “Hung Up” like an endless caffeine barrage.

31. “Love Tried to Welcome Me” from Bedtime Stories

Madonna contemplates sin, guilt, lust, and vulnerability in this seeming farewell to love. It’s the heart of the album, and perhaps the most intimate song in Madonna’s catalog.

30. “Impressive Instant” from Music

Our girl registers as a space cowboy in this trippy aeronautical blitz. Once she starts squeaking that she “likes to sing-y, sing-y, sing-y” and “rumba-rumba-rumba,” we’re too blissed out on rocket fuel and glitter to question her.

29. “Thief of Hearts” from Erotica

It does not get sweeter than this. Allow me to recite the slut-shaming rap that Madonna prattles off: “You do it / You take it / You screw it / You fake it/ Undo it / You break it / You’re over, you can’t take it.” Evil. And legendary.

28. “Your Honesty” from Remixed and Revisited

I’ll be honest: Though “Don’t Stop” is a nicely Madonna-fied version of new-jack swing, I wouldn’t have hated it if this discarded Bedtime Stories cut replaced it on the final track listing. “Your Honesty” is a bopping, swaying love train, and its ebullience is catchy as hell.

27. “Take A Bow” from Bedtime Stories

Madonna’s most successful single to date is a melancholic evisceration of a lover’s artifice, and its hopeless plain-spokenness makes it one of the finest examples of ‘90s balladry.

26. “Ray of Light” from Ray of Light

The song that renewed Madonna’s MTV credibility and earned her the Video Music Award for Video of the Year is an electrified, soaring sensation, and its lyrics are effing great: What could be a more exuberant statement than “And I feel – like I just got home”?

25. “Don’t Tell Me” from Music

More ranch-hand glitch-hop from Music, except this time Madonna’s a lonesome troubadour defending her very being while invoking some tried-and-true country music imagery. The whole whirs and gyrates like a lasso, and it’s an unmistakable radio moment of the early 2000s.

24. “Spotlight” from You Can Dance

There’s no telling why this bad-ass dancefloor beast is so underplayed. It features all the empowerment, urgency, defiance, and scrappiness of Madonna’s standards, and it even boasts the immortal line, “Everybody is a star.” This is your time to shine, dear listener!

23. “Music” from Music

It’s hard not to have mixed feelings about “Music”: The lyrics can be grating (and what could be a weirder introduction to the word “bourgeoisie”?), but it is a flopping, funky-ass porn star of a pop song, and it still feels fresh a complete decade after its debut. It’s like we just said “Hey, Mr. DJ” for the first time a second ago.

22. “Frozen” from Ray of Light

This sweeping dirge is sinister and mysterious, and it features a whole, unusual world of atmosphere that matches its cryptic lyrics. It might make you believe that henna is awesome again.


21. “Burning Up” from Madonna

As much as Madonna was something of a tartier Pat Benatar when she first arrived, she was also inspired by the punks of NYC – and this barebones, breathy war cry proves it. Though I dig the verses, its most unbeatable moment is its climactic “Oooh, ye-ah!”

20. “Crazy For You” from the Vision Quest soundtrack

Madge’s ultimate slow dance, “Crazy For You” is appropriate for a movie soundtrack about melodramatic high schoolers. It’s also undeniably sincere, and maybe that’s why Madonna long declared it her favorite entry in her old catalog.

19. “Lucky Star” from Madonna

A song like “Lucky Star” is so determinedly chipper that you might forget its naughtiest element – the way Madonna croons, “Shine your heavenly body.” Sort of like Prince’s “Gett Off” when he snaps, “Tonight, you’re a star – and I’m a big dipper.” Except Madonna’s version is softer, sexier, and of a piece with the song’s glittery resplendence.

18. “I’ll Remember” from the With Honors soundtrack

This watery ballad is both sentimental and defiant, which is a very compelling dichotomy. “I’ll Remember” was a huge hit for Madonna, and it once again cements her written-off ability to sell an emotional torch song.

17. “Material Girl” from Like a Virgin

While “Like a Virgin” is just overplayed, “Material Girl’s” winking decadence and snide coquettishness feel like very relevant parts of Madonna’s career. Though she will always be more Marlene Dietrich than Marilyn Monroe, I can’t deny how magnetic she is when she’s hiccupping madly after the chorus and accepting gifts from tuxedoed suitors.

16. “Causing a Commotion” from the Who’s That Girl? soundtrack

There is no such thing as an intense Madonna fan who isn’t obsessed with this song. “Causing a Commotion” is jubilant and driving, and Madonna concludes the song with a lyric that works as a mantra for her fanatics: “Quit wasting time / Make up your mind / And get into the groove.”

15. “Papa Don’t Preach” from True Blue

Madonna’s jump from Like A Virgin to True Blue required a new boldness and bigness, and “Papa Don’t Preach”’s righteous, fervent self-reliance is still stunning. I’m most moved by the second verse, in which she belts, “But my friends keep telling me to give it up / saying I’m too young, I oughta live it up.” Self-proclaimed alienation! A Madonna favorite!

14. “Secret” from Bedtime Stories

For a straight-up slice of R&B pop, “Secret” is unmatched. It’s meditative and moving and, most importantly, sexy as hell. And not just because Madonna is bustier than ever in the video.

13. “Rescue Me” from The Immaculate Collection

We can’t deny that Madonna slipped into a serious pretentious streak sometime over the past 15 years, but we can trace this trend back to one amazing song: “Rescue Me” combines Madonna’s love of spoken-word angst and self-revelation with a big, boundless chorus of pure soul. It remains one of her highest-debuting chart smashes.

12. “Over and Over” from Like a Virgin

All hail the highest non-single on our list (unless you include our #4 pick, which isn’t officially a single but remains Madonna’s highest-played radio tune). “Over and Over” is signature resilience matched with a ferocious pop melody. She’s taking no crap, and she’s indefatigable about it. She gets up again, over and over. Pure power.

11. “La Isla Bonita” from True Blue

Surely one of Madonna’s most timeless tracks is “La Isla Bonita,” the gentle, dreamy recollection of utopian San Pedro. As a romance, it’s touching, and as a personal reflection, it’s beautiful.

10. “Live to Tell” from True Blue

“Live to Tell” marks a critical juncture in Madonna’s career: Before then she was an armpit-drying urchin in Desperately Seeking Susan; afterward, she was a serious balladeer, one who was willing to break the rules of radio and release a six minute and twenty second song. “Live to Tell” is the closest thing Madonna’s ever delivered to a “sonic journey,” and it’s beautiful, indigo-tinged adventure in introspection.

9. “Like a Prayer” from Like a Prayer

Now, obviously “Like a Prayer” has been co-opted by overeager karaoke addicts and casual Madonna fans as a national anthem. I can kind of deal with that. What’s important is that “Like a Prayer” remains a truly spiritual, rigorously emotional dance song that kicked off a new era of Madonna: the topical button-pusher.

8. “Erotica” from Erotica

Long before Sasha Fierce entered the world, Madonna copped a ferocious alter-ego to launch an album: As actress Dita Parlo, Madonna took the whips-and-chains double entendre of “Erotica” and sold it like a primed burlesque mistress. It helps that “Erotica” is a hot, smutty grind of a dance anthem.

7. “Deeper and Deeper” from Erotica

Remember what I said about “Causing a Commotion”? That all real fans cling to it as a personal anthem? “Deeper and Deeper” is similar, as it amps up disco drama, arrives at a startingly poignant climax, and references “Vogue” in an amazing conclusion. Madonna called “Deeper and Deeper” a tribute to her dancefloor days, and it remains a DJ’s best friend in many a modern gay bar.

6. “Borderline” from Madonna

The desire and unabashed innocence of “Borderline” are classic enough, but I’m most attached to the phenomenal closing segment, wherein Madonna cries, “You cause me so much pain / I think I’m going insane / What does it take to make you see?” So cool and carnal and real.

5. “Open Your Heart” from True Blue

Madonna is partly revelatory because she makes a line like, “I’ll make you love me” seem like nothing but a righteous power play – but “Open Your Heart” is fabulous on its own. Demanding sincerity and vulnerability is Madonna’s strong suit, and “Open Your Heart” is a prized, urgent display of that asset.

4. “Into the Groove” from The Immaculate Collection

It’s no wonder that “Into the Groove” is Madonna’s most continuously replayed song on radio – it’s magnetic, comely, cool, and compulsively danceable. And it features that trademark confessional magic. If it were up to me, “Only when I’m dancing can I feel this free” would be printed on Old Glory.

3. “Express Yourself” from Like a Prayer

“Come on, girls. You believe in love? ‘Cause I’ve got something to say about it. And it goes something like this.” After an intro like that, most ideology would seem lovable and empowering, but “Express Yourself” is better than that. It’s a soulful imperative: Respect yourself, your man, and being honest “baby, ready or not.” Because you were born this way, see.

2. “Everybody” from Madonna

I abhor when people chalk up Madonna’s talents to marketing and reinvention. All you need is one listen of her gliding, club-dominating debut single, “Everybody” and her real talents are undeniable: She’s a commander, the Baryshnikov of pop chutzpah, and a rightful disco empress. “Dance and sing / Get up and do your thing,” we will.

1. “Vogue”

from I’m Breathless

Could there be any doubt? Vogueing is the perfect dance extension of Madonna as a pop culture entity: It’s self-presentational, winkingly narcissistic, actually narcissistic, a showcase of agility, funny, righteous, and fabulous. The song “Vogue,” meanwhile, is about Madonna’s two favorite things: self-expression and superstardom.

Whether you’re Joe nobody or Joe DiMaggio, you should be demanding attention – mainly from yourself. “Vogue” is Madonna’s greatest moment, the definitive ‘90s dance anthem, and a towering gay phenomenon that couldn’t be more ferocious or fun.