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.