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.