I hope this list isn't a thing that would piss Madonna off. (See my earlier list (shameless self-promotion).)
  1. Express Yourself
    Has a more empowering pop song ever been recorded?
  2. Like a Prayer
    Remember the controversy this video caused? Would people get so mad about a black Jesus today? Or was it that black Jesus was making out with a white pop star? Or was it that Jesus was making out with someone? Or that he was doing it in a church pew? Or was it the burning crosses? Man, that was a great video.
  3. Vogue
    But, seriously, how is it related to Dick Tracy?
  4. Live To Tell
    A song so sensational, I actually sat through At Close Range to figure out what "the secret [she] has learned...[that] will burn inside of [her]" is. SPOILER ALERT: they don't tell you. In their defense, it's a secret.
  5. Borderline
    I love the contrast between this song's bouncy, pop production and its borderline (did you get that?) dark lyrics.
  6. Ray of Light
    You know those old, suburban men who wear a lot of sweaters and are always watching The Weather Channel (perhaps as a substitute for porn)? They were the ONLY ones who knew the word "zephyr" before this song came out.
  7. Burning Up
    When I was around three, I was obsessed with this video. My parents took my fascination with Madonna's pavement writhing as an early glimmer of a crush. I was actually trying to learn her moves.
  8. Take a Bow
    Perfectly captures the beauty and sadness of saying goodbye. And, I believe, Madonna's longest stay in Billboard's #1 slot.
  9. This Used To Be My Playground
    This song put music and words to an emotion that I couldn't name at a time in my life when I should have been too young to have experienced it.
  10. Hung Up
    Listen to this song when you're stalking someone and you'll feel a little less alone. And a little more daring!
  11. Open Your Heart
    Apocryphal trivia: this song was originally titled "Follow Your Heart" and pitched to Cyndi Lauper, who turned it down. When it was brought to Madonna, she changed the title and thus got a writing credit and thousands of more dollars.
  12. Oh Father
    Not only might the video be David Fincher's best work, the song is haunting and scary and empathetic and sad and maybe the rawest we'd seen Madge get at the time of its release.
  13. Human Nature
    Express yourself; don't repress yourself. 'Nuff said.
  14. Secret
    A more negligible entry in the cannon for many but its lyrics emboldened me throughout the process of coming out.
  15. Bad Girl
  16. Cherish
  17. Girl Gone Wild
    It's stupid but it's SO FUN. Especially when you're pre-gaming. And, yes, you can pre-game after 30. Madonna taught me that.
  18. I'll Remember
  19. Ghosttown
    A post-apocalyptic love song: the perfect metaphor for how permanent and frightening love is. Also, great video with Terrence Howard that doesn't seem to be getting enough attention.
  20. 4 Minutes
  21. Crazy for You
  22. Papa Don't Preach
    I love it enough to ignore that "preach" and "trouble deep" is a near rhyme. At best.
  23. Rain
  24. Music
  25. Lucky Star
  26. Dress You Up
  27. Deeper and Deeper
  28. Like a Virgin
    Controversial to put in the middle of the list? Maybe. But as much as I respect its pop significance, I'm just kinda sick of it. And the allegedly sped up vocals in the original recording give it a girlishness that isn't as interesting to me as Madonna's genuine, throatier, real woman sounds.
  29. Keep It Together
    I love this song because I love my brothers and sisters and there aren't enough songs written about sibling relationships. Of course, it's kind of weird to listen to it now, knowing that a few years after it was recorded, one of Madonna's brothers would choose a pay day over his sister and write a tell all book.
  30. Don't Tell Me
  31. Turn Up the Radio
    Should've been the lead single off MDNA and should've been a much bigger hit
  32. Give Me All Your Luvin'
    IT MAKES NO SENSE BUT IT'S SO CATCHY. (Also, it's really fun to sing this song in bed but substitute dirty words.)
  33. Sorry
    When you've beyond You Oughta Know but aren't quite at Untouchable Face, this is a good one to play.
  34. Beautiful Stranger
    Moronic lyrics. But catchy. Also, plays in my head when flirting with a beautiful stranger.
  35. Everybody
  36. Miles Away
    Pop singles as therapy. For Madonna and me.
  37. You Must Love Me
    I love Madonna's performance in Evita and she shines particularly bright on this song, as it was written for the movie and thus there's no Patti LuPone or Elaine Paige recording to compare hers to. But both this and the more famous Don't Cry for me Argentina work better on context than as singles.
  38. Don't Cry for Me Argentina
  39. Jump
  40. Die Another Day
  41. Material Girl
    Another one that's solid but I'm just plain sick of. At least it hasn't been my nickname for 30 years. (Obviously, that's Material BOY.)
  42. Hanky Panky
  43. Frozen
  44. Rescue Me
  45. What It Feels Like for a Girl
    Fascinating concept for a song with some intriguing lyrics but ultimately not melodic enough to rank higher. But. I'm kind of into the Glee version of it. AND MADONNA TAUGHT ME I DON'T HAVE TO APOLOGIZE FOR IT.
  46. Who's That Girl
  47. American Pie
  48. Erotica
  49. True Blue
    The syrupy sincerity of this song gets on my nerves. But it is really memorable.
  50. Bedtime Story
  51. Hollywood
    Although I'm not sure if I can distinguish between Hollywood the Single and Hollywood the Gap Commercial With Missy Elliott and the Mashup
  52. Holiday
    The one of which I'm sickest
  53. You'll See
    Cliched and unspecific but kinda works (especially in the context of its sequel-to-Take-a-Bow video)
  54. La Isla Bonita
  55. American Life
    This song would be infinitely better and pretty fantastic...were it not for Madonna's rap.
  56. Love Don't Live Here Anymore
  57. Justify My Love
    Others have gasped when I admit to finding this song overrated. But separate it from its controversial video and it's little more than highly ambient sex music.
  58. Causing a Commotion
  59. Nothing Really Matters
    The great rarity: a song with excellent verses and a forgettable chorus
  60. The Power of Goodbye
  61. Love Profusion
    Great chorus; can't remember the verse. Was this used in a Garnier Fructisse commercial?
  62. Living for Love
    Not specific enough to be truly remarkable but decent with a great video and, now, because of the Brit awards, an interesting story attached to it.
  63. Give It 2 Me
    She loses me with the "get stupid" bridge
  64. Get Together
  65. Celebration
    It's a testament to Madge's cannon that the first single I'm "meh" about is 65 of 67.
  66. Angel
  67. Nothing Fails
    Except this single. BOOM. LISTED.