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.
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.