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.