Madonna as an appalling MS Paint image

Madonna Singles Ranked, 31-40

Originally Published at Facebook Notes (July 13, 2017)

Every few days or weeks, I pick a music artist or band, compile a chronological playlist of all of their singles (based on Wikipedia, Discogs and a few other sources) and then try to arrange that playlist in such a way that I like each song more than the previous song. Rearranging the songs is a never ending process so once I’m at a point where I think I’m pretty close to how I feel, I share the results with you 10 or so songs at a time. I’ve come to define “singles” in a pretty broad way so that it includes any song that was used to promote an album (via video or single) or any song that charted in a significant way. Generally speaking, I don’t include remixes or live versions of songs that were previously released as singles.

So, I started a website called According to Doyle so I can host (and eventually write) these lists off of Facebook Notes. I’ve copied my lists of U2, The Cure and Kate Bush singles over there so far. Ch-ch-check it out.

We’re in the Madonna Top 40, so let’s get cracking!

40. I’ll Remember

From the soundtrack of the 1994 film With Honors, First Single

Wait, what is this song and why is it so high up this list?

*hits play*

Oh, this song. Yeah, this is really good. Apparently, there was a movie called With Honors. Hunh. I had no idea. Also, back in 1994, this song was something of a comeback hit for Madonna. I did not know that.

39. Open Your Heart

From 1986’s True Blue, Fourth Single

This is the last song from True Blue on my list. Originally written as a rock song for Cyndi Lauper, Madonna took the song and changed both the lyrics and the musical approach to turn it into a dance/pop song (and one steeped in the best 80’s musical cliches). It was her fifth #1 hit and featured one of her more controversial videos. There’s been a lot of debate about whether the video is exploiting Madonna or whether it is critiquing the male gaze. The first time I saw it – in context of the reigning King of Pop, Michael Jackson – I thought it was Madonna trying to play up her sexuality but also play herself up as family friendly (via her friendship with the little boy). I mean, I was 19. What the hell did I know? The ending – She and the kid dancing off down the street – totally felt like a Michael Jackson video to me. That might just have been because that was the music video language we had in the mid-80’s. Anyhow, the song has mildly suggestive lyrics which I managed to completely miss until 2017. Lock and key, indeed. Its a favorite.

38. Holiday

From 1983’s Madonna, Third Single

I know, I know, I like 37 songs better than “Holiday,” but I do. This is another track that I first heard on our college station, WXCI, and it was also her first top 40 hit, peaking at a respectable #16. For an artist that was getting airplay on college stations, a #16 hit was a pretty big deal. If her songs had continued to hit in the mid-teens, I probably would have stayed on her bandwagon longer but as soon as she had a top 10 hit – her next single, “Lucky Star” – obviously she must be a sell out. Never mind that I was just jamming to the song on WXCI the month before and that Madonna hadn’t really had a chance to change anything in order to sell out. Logic holds no sway over the true believer! And I truly believed that success must be a sign that an artist was doing something wrong. Man, this idea that success means failure that gets beaten into many young artists heads by society (and by the bruised egos of failed artists) is a lousy thing. Having a bunch of failed singles doesn’t mean you necessarily suck artistically – but maybe you do. Having a bunch of successful singles doesn’t mean you are necessarily a great artist – but maybe you are. I should have spent more time judging things by how much I enjoyed them and less time shutting out stuff just because it was popular. Especially since I was totally addicted to American Top 40. What the heck!

37. Love Spent

From 2012’s MDNA, Netherlands Single Only

Madonna did not write “Material Girl” but that song came to define her (certainly in the 80’s) more than the songs she wrote. I remember her being introduced more than once as “the material girl.” I guess they weren’t saying she was a gold digger… “Material Girl” was a song about basic 80’s “greed is good” philosophy. Its worth noting that George “Can’t Buy Me Love” Harrison (he did not write that song) got a certain amount of critique for acknowledging that persuing love did, in fact, require some money in 1987’s “Got My Mind Set On You.” Madonna touched on the love vs money debate a few times in her career but of all of her songs on this theme, I think “Love Spent” is the clearest response song to her earlier it. In this tune, her paramour cares more about his cash than about her. She is asking that he treat her like he treats his money – she’s come around to the “money can’t buy me love” position. The song starts off with a banjo (which returns to great effect in the bridge) before turning into a driving dance tune with a strong string stings. Its perhaps my favorite song from MDNA (and the highest ranking one on this list) and I’m glad it was released as a single somewhere.

36. Now I’m Following You

From 1990’s I’m Breathless: Music from and inspired by the film Dick Tracy, Song that Charted

This is my second favorite tune from I’m Breathless. It starts as an old-timey sounding pop standard before turning into an occasionally hilarious dance remix of itself. Madonna’s then-boyfriend Warren Beatty duets with her here and, to his credit, he doesn’t embarrass himself. While the song wasn’t released as a single, it did place on the dance charts and I imagine it must have been good fun to dance to it in 1990, though I wouldn’t know because I was inside theatres for pretty much 18 hours every day and didn’t know for sure if the outside world had survived or not. Anyhow, every time she starts playing around with Dick Tracy’s name in the middle of the remix, I move this song up another notch so it was time to work on this section of the list before my love of well executed filthy jokes led this song to the top of the my rankings.

35. Nothing Fails

From 2003’s American Life, Third Single

“Nothing Fails” is an agnostic gospel song with a dance beat. Its sort of natural, if you’ve followed the arc of Madonna’s career, to connect this song to “Like a Prayer,’ particularly because this is another song where meeting the love of her life makes her “want to pray.” The choir sections are especially well done especially if you – like me – are a big fan of backing vocals. It took me a few weeks to get into this particular track but now its one of my favorite ones to use when I trail dance.

34. Erotica

From 1992’s Erotica, First Single

Madonna and her sexual fantasies were everywhere in 1992. I know many people feel like she jumped the shark after the Erotica album, the Sex book and the Truth or Dare film. My bad luck, I suppose, that I was just getting onto the Madonna train as other people were getting off (see what I did there?). “Erotica” is the first song on my list to which I’ve assigned five stars in iTunes. So its my least favorite Madonna five star song. Which means I love it but it would be the last one I’d rescue if my MP3 collection was on fire (presumably by clicking and dragging them into a picture of a lake or something). “Erotica” was one of Madonna’s first and most successful forays into trip-hop. I was still working on one of my graduate degrees and, thus, never smelled the ocean breeze unless somebody accidentally propped a door in Kennedy Theatre at UHM open but I wish I’d gotten out to a dance club just to see how the kids in those days boogied down to this number (prediction – there was some touching).

33. Love Profusion

From 2003’s American Life, Fourth Single

I really appreciate that Madonna decided she wanted to include more guitar in her songs again in the 21st century. While she frequently plays the guitar in concert, American Life producer Mirwais Ahmadzaï plays it on this particular track. According to Wikipedia, “Love Profusion” was a love letter to her then-husband Guy Ritchie. I hear that – the vocal is heartfelt and genuine. Madonna and Ahmadzaï find a strong balance between the folk rock elements of the song and the dance mixing that is the signature of Madonna’s 21st century work.

32. Sorry

From 2005’s Confessions on a Dance Floor, Second Single

Confessions on a Dance Floor is mixed like one continuous track. Drop the needle on it, stick it into your cassette deck, slip the CD into the changer or hit play on your digital platform of choice and you basically have an hour long party. “Sorry” feels a bit to me like a Giorgio Moroder-style disco number (though I also agree with the various critics who say it sounds like a Pet Shop Boys tune) in the best posible way. You have your throbbing dance beat, your half a dozen languages and a vocal line that is measured and controlled throughout. Its one of the best dance tracks on a great dance album.

31 Keep It Together

From 1989’s Like a Prayer, Sixth Single

I really try hard to separate songs from context as I write about them, but that is a complete fools errand. Context – where we heard them, what we associate them with, etc – is inexorably linked to how we react to different songs. For example, the song “Nightshift” by The Commodores was popular when my grandfather passed away in 1985 and I can’t hear that song without thinking about that instantly. My connection with “Keep It Together” is nothing quite so personal or painful. I first realized consciously that I really genuinely liked Madonna after watching the documentary Truth or Dare. This song figures prominently in that movie and I can’t hear it without realizing that hearing this song in that film is the thing that changed my opinion about her. The lyrics are about the tension between how much one’s family can drive one crazy (especially when you’re a teenager) and how much you love and value them at the same time. I had a really great relationship with my family (I’m in the “all happy families are the same” category) but I recognize that Madonna also means the families we choose (in the movie, its her dancers). I’m going to stop myself before I ramble. Suffice to say I was singing “keep people together for ever and ever” on my way out of the movie for like nine hours.

Coming Soon: The last two marquee collaborations on this list.

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