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.
Here we are at my Madonna top 10. This was the longest list I’ve worked on yet and it was both easier and harder than I thought it would be. It was easy in the sense that I found I have had something to write about every song – I worried I wouldn’t have anything to say about some of them. Granted, I’ve had nothing important to say about almost any of them but some words are more than no words. It was harder in the sense that more songs makes my ranking method a much more rapidly moving target. Like when I wrote about The Police, my top ten were basically my top ten the whole time. They only had 28 singles which meant I was finished with the project in a snap and didn’t have time to reflect upon my bad choices. Every time I posted one of these lists – especially when I had over 50 songs to go – I would read the responses and go “wow, everyone else in the world seems to dig ‘Cherish…’ what am I missing?” and then would reevaluate everything that came next. Usually this meant that 21st century songs were judged more favorably (which I don’t think was anywhere near the intent of the folks who love “Cherish” but that was ultimately the effect).
Anyhow, only two 21st century songs on this portion of the list. Let’s finish this!
10. Deeper and Deeper
From 1992’s Erotica, Second Single
We like songs for all sorts of silly, personal reasons. Way back in 1994, I was working on a production of the model revolutionary jingju (“Beijing opera”) titled Shajiabang at the University of Hawaii at Manoa, as one does. In the men’s dressing room – for reasons that elude me to this day – my friend Harry either claimed control of the boom box or was ceded sole decision making status regarding what music we’d be listening to on any given night. The make-up process for jingju is lengthy and Harry decided the best thing for it would be to play this song over and over again for the entire length of the run of the show. At first, it was funny. Then, it was annoying. Then, it was maddening. Then, it was funny again. Eventually, it was expected. Its like we went through the five stages of earworm grief. It was many years after that production ended that I heard this song again and I felt nothing but happy nostalgia for that production. Its a really good song, too, but most of my feelings about it are tied up with jingju. The human brain is a strange thing.
9. Burning Up
From 1983’s Madonna, Second Single
This is the best track from Madonna’s debut album. It reminds me a bunch of Grace Jones’ contemporaneous work (indeed, I’d love to hear Grace Jones perform this). I sort of didn’t pay a whole lot of attention to this song until Sonic Youth and Mike Watts of The Minutemen created the somewhat tongue-in-cheek Madonna tribute Ciconne Youth Whitey Album which included Mike Watts lo-fi solo version of the song. Something about hearing the song stripped bare like that let me hear Madonna’s original differently. Madonna’s very earliest recordings have a bit more of a punk edge to them but this is maybe the only song on her debut that really preserves that edge – it features much more guitar work than you might remember. “Burning Up” is a relentless expression of repressed desire.
8. Express Yourself
From 1989’s Like a Prayer, Second Single
I had no idea I liked this song so much but every time it comes on and I hear Madonna yell “Come on girls, Do you believe in love,” I’m sold. Like a Prayer is an album, in many ways, about being an adult. Madonna had a huge audience of young people in the early 80’s and she calculated that it was time for her music and lyrical content to grow up with them. In some ways, this song is a rejection of “Material Girl” (I always use the “Satin sheets are very romantic/what happens when you’re not in bed?” line as an example of Madonna poking at the former song). She encourages her listeners to express how they feel so they can get what they want – if you never say it, you’ll never even have a chance to get it. As it happens, this positive message is accompanied by one of the most upbeat and just plain fun compositions in her catalog. Try not to dance. I dare you.
7. Hung Up
From 2005’s Confessions on a Dance Floor, First Single
Madonna had one of the biggest hits of her career in 2005. “Hung Up” went to number 1 in 41 countries, establishing a record in the Guinness Book of World Records that has yet to be beat. It has sold more than 9 million copies worldwide during the digital age. I mean, its ludicrous how successful this song was. The song is built in part around a sample of Abba’s “Gimme Gimme Gimme” (part of the goal of Confessions on a Dance Floor was to capture and update the vibe of late 70’s disco for the 21st century) and the tune brought in some serious money to Abba’s Benny Anderson and Bjorn Ulvaeus. 22 years into her career and Madonna could still blast a song into the stratosphere. Think of all of the pop careers that rose, flourished and collapsed during those 22 years! Madonna is a beast. She can’t be stopped. Here’s the strange thing – I missed this song completely in 2005 and it was just another late-period Madonna track when I started the close-listening that accompanies these lists. The first time I heard it, I gasped and dropped it into the top 20. It took me like eight or nine listens of the other songs before I felt comfortable ranking them but I knew as soon as I heard this one that I loved it. I might have missed it 12 years ago, but I’ve listened to it like 50 times this month on repeat.
From 1994’s Bedtime Stories, First Single
“Secret” manages to be a song about having a secret that sounds like what a secret sounds like. Does that make sense? I don’t know. But both musically and lyrically it feels like there’s something going on that we’re not quite privy to. The chorus has always felt a little spooky to me – I love the “mmmm” part especially. Its not a Kate Bush “mmmm” but its a pretty effective “mmmm” none the less. When I first heard “Secret” in 1994, I was already in a place where I thought Madonna was pretty brilliant and this song blew me away. I wasn’t listening to much radio but I was watching a lot of MTV at the time and I kept waiting to see this video (when “Take A Bow” came into rotation, I was resentful that it wasn’t “Secret”). I still get excited when I hear the opening guitar. Like I feel my heart starting to race excited. So good.
5. Don’t Tell Me
From 2000’s Music, Second Single
I. Love. This. Song. Every one of my top five Madonna songs would be a contender for my “top ten songs by anyone” list. Deciding which one I liked best (and how to order these five) was next to impossible. I did it and I’m standing by it in-so-much as I want to finish this list and publish it, but really ask me again in two days and I might shuffle them all completely again. I love the start and stop production business. I love the melody. I love singing along with it. I think the lyrics are generally pretty great. It makes me want to dance. I mean, everything everything. In 2000, when she released the song “Music,” I figured she’d released the best song off of the album first, but she was just getting us warmed up for “Don’t Tell Me.” Her vocals are warm and soulful – I think she sounds just fantastic on the whole song.
From 1990’s I’m Breathless: Music From and Inspired By The Film Dick Tracy, First Single
“Vogue” has absolutely nothing to do with Dick Tracy. It is neither from that film nor inspired by that film. I was swamped in college radio from 1985 through 1993 and only very poked my head into the world of popular music. Thus, if we’re playing name that tune, I can nail almost everything from 1980 to 1985 but struggle a bit more with 1986 to 1990 (basically, I ignored hair metal). When I did pop my head up, groundhog-like, into the world of contemporary popular music long enough to hear “Vogue” in 1990 my brain did a “Whaaaaaaaat?” double take. I’d heard and enjoyed Like a Prayer and its singles but even though I felt she was expanding her acoustic palette, it wasn’t until “Vogue” came out that I started thinking “this Madonna person – she’s on to something.” Then I saw the performance on the MTV music awards and I was just completely sold. Madonna says she was both inspired by and paying tribute to the gay club scene’s dance craze though there’s an argument to be made (and others have made it better than I could) that she was appropriating culture. That’s a topic that is beyond the scope of my rankings, but its surely worth discussing. At the time, the song was bold, shocking, infectious and cool as heck. It still is.
3. Into the Groove
From the Soundtrack to the 1985 Film Desperately Seeking Susan
Desperately Seeking Susan was a good movie with a strong debut by Madonna. I stand by my earlier theory (touched on when I was writing about “This Used To Be My Playground”) that Madonna has the potential to be a good actress if she is cast in the correct role and and listens to her director. I imagine its hard when you’re the strict custodian of your own image to listen to what somebody else thinks will make you look good on film. Anyhow, “Into The Groove” is a great song built around a double-entendre (“groove” might mean something other than “rhythm”) that may have been unintentional. But I suspect it was intentional. Because I think Madonna usually knows exactly what she’s doing. I liked this song all right when it first came out but my opinion of it was radically altered when Sonic Youth put out their Ciccone Youth cover of the song. I’ve heard it completely differently since then – I feel like it is a pre-”Express Yourself” call for female empowerment. Good stuff.
2. Like a Prayer
From 1989’s Like a Prayer, First Single
I mildly enjoyed “Like a Prayer” when it first came out but, of all of Madonna’s 80’s songs, this is the one that I think has improved most with age. There’s still a little touch of the 80’s club sound going on, but its subtle and doesn’t necessarily lock the song down in that decade. The song combines elements of gospel, funk and dance – I encourage you to read about Madonna’s working method as the song was created. To whit, this song doesn’t sound like her first vision but it is what she wanted it to be. Lyrically, she balances double-entendre with more spiritual concerns in an especially provocative way. However, she sort of turns this on its ear – she’s using the innuendo to get you to think about the spiritual angle instead of vice versa. Its an extremely well-thought out, well-constructed pop song that rewards repeat listening. As I’ve documented elsewhere during this list, its my belief that this album (and specifically this song) represents a major turning point in her development as an artist. She freed herself from her identity as an 80’s pop icon and gave herself permission to experiment and explore – something that has allowed her to remain a vital and active artist for decades. Also, its a really, really great song.
1. Ray of Light
From 1998’s Ray of Light, Second Single
Just try to sing along. This song goes everywhere. My friend Rick just pointed me in the direction of her 1998 MTV VMA aware performance where she struggles to hit the notes. On the other hand, she sounds fabulous singing it on Oprah. And in 2006 on the Conessions tour, she rocked it. But, yeah, the song is crazy crazy hard. Anyhow, that’s not what I was originally going to write here but Rick sent me down a rabbit hole of performance videos just as I’d started writing this.
The book Gödel, Escher, Bach: An Eternal Golden Braid has made the rounds in my friends circles several times (exclusively in the 80’s). There’s a particularly interesting discussion about a Bach piece called The Musical Offering. Without going into too much detail, the piece sort of rises and rises as if its rising up to heaven. While I’m not comparing it to Bach’s piece in terms of composition, I feel that something similar is going on with the musical intent of “Ray of Light.” The music (including the vocal) has a sense of rising up to the heavens which suits a song that is about a woman flying into the universe at faster-than-light speed. I find it to be one of the most exhilarating pieces of pop music released in my lifetime. I might shuffle around my other top five selections, but I suspect this would always be my number one choice. It makes me feel like I can take on the world when its playing. Maybe I need to take a cue from my friend Harry’s love for “Deeper and Deeper” and just let this song play all the time everywhere I go. Bravo, Madonna.
Coming Soon: Duran Duran because I just saw them in concert or Thomas Dolby because he only has like 25 singles or Talking Heads because I think I could actually start writing about them like tomorrow with hardly any prep work.