My top 20 Madonna songs

A while back, my friend Matt – who is a fellow Fleetwood Mac fan – challenged me to rank my top 20 favorite Fleetwood Mac songs, in order.  The experience was excruciating, but the results were interesting, to say the least.  We were saying how fun it would be to do that again, but alas, Fleetwood Mac is the extent of our musical overlap.  There are a ton of artists I could do this with and there were an equal number he could do but Fleetwood Mac would be the only one that we could do together.  This got me to thinking about how I would rank the songs of my most beloved artists and how it could be a fun challenge, even if I was just doing this by myself.  I figured I might as well jump in with both feet and try to rank my top 20 Madge songs.

This was both easier and harder than I thought.  It is easy to instantly place all her biggest, most recognizable hits on the list, but when I got to thinking about it, is “Like A Virgin” really one of my top 20 favorite Madonna songs?  It’s probably in the top 50, but it doesn’t even come close to the top 20.  In fact, it didn’t even make my first cut of around 40 songs.  So many songs that you’d think would be right up there in the top 10 didn’t and some surprisingly underplayed songs in my library did end up not only surviving the cut, but placing higher than I would have otherwise thought.

I had a few criteria – only official studio recordings were allowed.  Also no live versions – otherwise the Confessions Tour version of “Erotica” would have undoubtedly placed on this list.  I also eliminated demos and leaked tracks.

The final cuts were the hardest to make – how could I possibly cut “Crazy For You”?  It seems unspeakable, but I did it.  It came in at number 21, if that’s any consolation.

Here’s the list, screen captured straight from iTunes.  You may need to click it to make it bigger – that’s as big as I could make it in the post. Caution: heresy, dead ahead.

Screen Shot 2014-07-29 at 2.34.31 PM

A few thoughts:

  • For those that know me, #1 should be no surprise to anyone. “Borderline” has long been my favorite Madonna song – a perfect pop song that has been with me for as long as I’ve been a Madonna fan. It seems a bit crazy to rank it before “Vogue” or “Like A Prayer” but it’s my damn list and I say #1 is “Borderline.”  It also has the best fade-out of any song ever recorded.
  • I feel like I owe an apology to every song that didn’t make this list because “Revolver” made this list.  I can’t help it, I really do love that damn song.  I chalk it up to the awesome live performance of “Revolver” at the MDNA Tour and Heidi playing it constantly when she was writing Double Blind.  It turned what I initially called a Britney Spears reject into one of my favorite Madonna songs.  It still uses too much autotune, but you can’t win ’em all.
  • “Don’t Tell Me” is one of Madonna’s smartest singles.  It is so unlike anything she’s done before or since.  Expect it on the next tour – we’re about due.
  • Erotica is one of my favorite Madonna albums, yet only “Deeper and Deeper” ended up on this list.  That was the song that jumped out at me when I first heard the album.  In all honesty, it probably should have been the lead single vs. “Erotica.”  I wonder if things would have gone differently for that album with just that small change.
  • There’s a paucity of Ray of Light on this list, with only “Nothing Really Matters” sneaking in at #19.  “Frozen” was probably #23 or #24, but “Nothing Really Matters” is still my favorite track off of Ray of Light. I remember thinking back then about how Madonna didn’t seem as “fun” during the ROL years, but whenever I thought she’d lost her touch, I’d listen to “Nothing Really Matters” and my faith would be restored.
  • “Oh Father” is the highest ranking ballad on this list and is, quite simply, the best ballad she’s ever done.  Criminally underappreciated, I love it even though it was the song that broke her streak of 17 consecutive Top 10 singles by stalling out at #20.  I think it’s one of her most personal songs and the top notch video by David Fincher is one of her best.
  • I’m amazed at how well “Like A Prayer” holds up after all these years.  I remember hearing it initially and being taken aback by the odd song structure, but her voice is so strong and of course, there’s the unforgettable visuals that are impossible to separate from the song.  I feel that “Like A Prayer” will be one of those classic songs that people talk about 30 years from now, even as we’re 25 years out from it now.
  • I can hear the peanut gallery now. HOW did “Girl Gone Wild” make it to the Top 10?  What can I say? There’s nothing that should make me like this song any more or less than some of her other disposable latter day “hits.”  It was probably the MDNA Tour that did it – it was a perfect show opener.  It’s also just plain fun.  Heidi said once that she wasn’t sure how she felt about a 55 year old woman being a “girl gone wild” but I’m kind of whatever works.  I think this is a great great Madonna song not in terms of lyrics or originality, but it sounds amazing when you play it loud.  Sometimes, we just want to have fun.
  • My friend Jeff will surely die when he sees “Human Nature” on this list.  I’m not sorry that it’s there.  May she continue to perform it on tour because it’s the Madonna songs that addresses the Madonna experience more than any other.
  • Madonna fans seem to be divided into Team This Used To Be My Playground and Team I’ll Remember.  I am firmly Team I’ll Remember.  It came out at a critical time in my life and spoke to a lot of struggles I was facing at the time. “Playground” can die in a fire.

It feels wrong to put this out there, because I’m sure it will change, but it reflects what 30 years of Madonna fandom hath wrought.  You can also listen to and/or subscribe to this playlist on Spotify if you’re the Spotifying type.

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5 Responses to My top 20 Madonna songs

  1. John says:

    Love this…the only omission I’m surprised by is “Dress You Up.” I figured a hook that strong would have been a given for you.

    • Dan says:

      I was surprised by the relative lack of LAV songs on the list. Only Over & Over made it and honestly, that has a lot to do with how much that song is a personal anthem for me.

  2. Tony says:

    But do you prefer the immaculate collection edit of borderline? I prefer the single version of a Express Yourself myself. Speaking of live versions, I also love the Erotica version on Confessions, but Like A Virgin in Blond Ambition take the prize in my book 🙂 did you like the ?Glee mashup of Borderline/Open Your Heart?

    • Dan says:

      I prefer the edit of “Borderline” to the album version – I think it’s a lot tighter. The single version of “Express Yourself” is probably superior, although the mix used for the video when it premiered and I don’t think I’ve ever heard it since. (The album version got dubbed over if I recall correctly.)

      And yeah, the Glee mashup is great – I still listen to it even though I haven’t watched Glee in forever!

  3. Bas says:

    Surely Team I’ll remember forever! Agree with you: Playground can die in a fire (that one made me laugh). My fav Madonna song of all time must be *drums* Hollywood!

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