(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.)
From 1987’s You Can Dance, First Single
You Can Dance was an album of remixes released in 1987. On the album version of “Spotlight,” you can hear the song fading into a remix of “Holiday” as it ends, which is significant because it was composed specifically to sound like “Holiday” after that song was a success. While it was not released as a single in the U.S., it did receive enough airplay at the time to chart on the, well, airplay charts. If you were listening to the radio in 1987 or going to dances/clubs, you very likely hear this song. You may also have been unaware that you heard this song because its about as generic an 80’s Madonna song as was ever created. Still, its fun enough to shout “spotlight” at the appropriate times.
69. Dear Jessie
From 1989’s Like a Prayer, Fifth Single
The line between psychedelic music and absurd children’s music is sometimes razor thin. In the late 80’s, there was this movement called the Paisley Underground in California. Bands grouped under this loose label included The Dream Syndicate, Game Theory, The Three O’Clock, and (most notably for this discussion) The Bangles. Prince was a big fan – he named his label Paisley Park, wrote “Manic Monday” for The Bangles and signed The Three O’Clock to his aforementioned label. His 1985 Around the World In A Day album was his most significant embrace of this style. Notably, he was a collaborator with Madonna on Like a Prayer. There’s no suggestion that Prince worked specifically on this song, but I think there’s an influence. Anyhow, while recording the album, Madonna befriended Jessie, daughter of album producer Patrick Leonard and agreed to record a song he’d written about her. What emerged is a one of Madonna’s most atypical singles – it sounds like a kid’s song in the style of Sgt. Pepper’s which is not necessarily a bad thing. Its ok.
68. Nobody Knows Me
From 2003’s American Life, Promotional Single Only
With this song, we’ve officially entered the realm of “I like these songs but I like other songs more.” I’m sort of stunned to realize I am at least mildly enthusiastic about 68 of her singles, but there you go. “Nobody Knows Me” has slid all over my list in the last month and its landed here. Give me another week and it will be in the top 30 again. I recognize that a significant chunk of the music world stopped noticing Madonna after around 2000 (because we got old, yo) but she kept having huge hits and creating great songs. “Nobody Knows Me” is a low-key but infectious dance track that has a great bridge (it starts with “I don’t want no lies/I don’t watch TV”). I have danced to this one on several trails on Oahu. There’s this one lyric about social diseases that I flip flop on loving and hating and right now, I’m on the dislike part of that curve, but I’m coming around again.
From the 2009 Greatest Hits album Celebration, First Single
“Celebration” is like 4/5 of a great song. I love the verses – there’s this great fast/low rhythm thing going on that is present in a lot of the great dance music of this century (I keep hearing Justin Timberlake when I listen but I think many other singers have used a similar approach). The chorus is also pretty fantastic – it falls in the tradition of Madonna-tells-you-to-party songs. I just want more of these two things. I feel like we get like 90 seconds of awesome and then some dance beats that are fine, but not as awesome as the first 90 seconds. I also appreciate that Madonna flips the hackneyed “male singer uses lame spoken word pick-up lines on female subject of dance song” cliche. The spoken word lyrics for that section are a little lame, but I think that’s the point.
66. One More Chance
From 1995’s Something to Remember, Second Single
Putting aside for the moment that the acoustic strumming at the top calls to mind the appalling “More Than Words” by Extreme, this is a pretty ballad with a better-than-average vocal performance from Madonna. I really dig the simplicity of this tune – I was really into her forays into electronica and trance in the 90’s and, you may recall, this led me to be pretty turned off by Something to Remember. Madonna was training for Evita at the time and, thus, there’s a real sense that she’s taking a risk here and just letting her vocals be the star of this song. It works quite well actually.
65. Hey You
2007 Stand Alone Single for the Live Earth campaign
Another somewhat atypical song, Madonna recorded this one specifically for the Live Earth campaign. A worthy campaign, to be sure. At the time it was released, I wasn’t aware of the campaign and just thought it was a positive message song aimed at people who were experience depression (an interesting song to contract with ‘The Ledge” by The Replacements from my last list – Paul Westerberg makes struggling with depression into a deliberate and provocative horror show while Madonna and collaborator Pharrell Williams want you to know there’s hope and things will get better). I find this song interesting because I really, really enjoy it while I’m listening to it and then have an impossible time dredging it up from my short term memory once its over. But every time it comes on I’m like “Oh, I like this song.”
64. You Must Love Me
From the soundtrack to the 1996 film Evita, First Single
Madonna really worked her butt off to prepare for Evita. This song has yet to make a significant impression on me when I watch the musical live (presumably because I have no soul, though I’d argue its because I have a hard time empathizing with either Peron). Stripped away from the musical and performed by Madonna, I think… well… I guess it works pretty well. I sometimes ever find myself feeling almost moved by it. I don’t really know how it came across on screen because I NEVER WATCHED THE MOVIE. I had other things to do in the mid-late 1990’s – like fall out of touch with music and learn how to teach high school students. The good news is this means that I am able to listen to the songs as singles if I can’t remember them from the productions I’ve seen of Evita. Anyhow, good job to Madonna. This isn’t a song I need to seek out, but she sings it with honestly and passion.
63. Pray for Spanish Eyes
From 1989’s Like a Prayer, Released in Spain only
I was pleasantly surprised to learn that this had been released as a single in Spain because I really, really like the “I light this candle” turn into the chorus, especially as the song progresses. Madonna friend and dance teacher, Christopher Flynn, died of AIDS in the 80’s and this song was written about him. In the initial pressings of Like a Prayer, Madonna included a pamphlet with AIDS safety education information – which was (sadly) a pretty ballsy thing to do even in the late 80’s. Anyhow, this is another song where Madonna sounds genuine and passionate – its interesting to listen to how raw that sounds on this track as compared to her more practiced vocal on “You Must Love Me.”
From 2000’s Music, Columbia single only
“Amazing” is the last (and best) song on this list that falls into the “I can’t remember it five minutes after I hear it” category. The shift into the chorus is almost perfect (I wish she’d pulled a Garbage and really let the beat and instrumentation kick in heavy). Music era Madonna was one of my favorite periods in her career. Part of this was I had a sense in the late 90’s that electronic dance music had finally caught up to the way I’d always wanted it to sound (indeed, the techno, industrial and electronic music of the 90’s is among my favorite of all time) but part of it is that Madonna seemed to be having a blast. I feel like starting with Ray of Light through Music she created some of her least self-conscious and most joyous music. Even the sad songs are exhilarating. So maybe this one doesn’t stick in my head, but I want to jump up and down and shout “yes yes yes” when its playing. It scratches that electronic itch I always have.
61. Girl Gone Wild
From 2012’s MDNA, Second Single
This is another song that’s been slowly creeping up this list as the weeks have gone by – it was in the bottom ten and each time I’ve worked on a section of the list, I’ve kicked it up to the next section. Its a genuinely infectious rave number with a lyrical shout out to a Cyndi Lauper classic and a killer beat. I love the bridge (“I know I know I know”) and always appreciate a call-out to the Roland 808 drum machine – in part because I like the drum machine and in part because I live in Hawaii, the 808 area code state. Its silly, but I get a kick out of that. The only thing that makes me wince a little when I listen to this otherwise great song is the “Oh my God” intro faux-prayer. On the one hand, I appreciate that Madonna has been consistent over her career in her choice of targets (she has stated that her critique of religion is usually a reflection of her more general critique of patriarchal power structures so good on her). On the other hand, this comes across almost as a parody or tribute-band level reiteration of themes that she’s been exploring for decades – its a Madonna’s been there/done that (and done it better) thing in my brain. But once I get past that part, whoa, great song.
Coming Soon: Three more all time classics disrespected because they all can’t be number 1.