(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.)
There’s several classics on this chunk of list, but I want to mention a classic that I just moved up the list as an example of my working method. For several weeks, “Crazy For You” was hovering around 75 or 76 and then something just clicked for me with that song this week. I think it was suddenly noticing the clarinet (that is a clarinet, right? I’ll try to confirm by the time I get to the song) and then that led me to notice how genuine Madonna’s vocal commitment is on that song which made me suddenly like it a lot more than I had previously. So, basically, as with all of these lists, if I were to do this again in a year or two, the results might not only be different but might be alarmingly differently. Alarming to me.
I predict that there will be objections to at least five of these rankings.
80. Love Don’t Live Here Anymore
From 1995’s Something to Remember, Third Single
When I first started ranking songs, I avoided including covers in my rankings. My initial reasoning was that the process of responding to a cover is a different thing from responding to an original song. When I listen to a cover, I always ask “why is this artist covering this song?” I don’t mean that in a negative way, but I do mean it in a critical way – as in “critical thinking.” So, basically, I have a difficult time listening to a cover without also including my feelings about the original song in my response. Rose Royce’s original “Love Don’t Live Here Anymore” is a terrific R&B song with one of the first recorded uses of the LinnDrum. Gwen Dickey’s seasoned vocal performance is at turns restrained and passionate. Madonna recorded the song originally while working on Like a Virgin in 1984 and, it was much more of a vocal stretch for her then than it would have been by the mid-90’s – her voice has kept improving and improving over time. The single is a remixed version from her 1995 ballad album Something to Remember. I think she reaches a nice dramatic vocal peak by the end of the song, but I also think the song was a bit of a reach goal for her in 1984 and she didn’t quite reach it. I’d love to hear her sing it now – its the sort of song that she’d probably slay live. That said, I genuinely don’t care for the lush production – it strips the soul right out of the song. I might like it better if I wasn’t familiar with the original…
From 1984’s Like a Virgin, Third Single
To be clear, this section of songs is still in the “I can take them or leave them” grouping and not in the “I don’t much like them. nope” grouping. Whenever I’m down on an 80’s Madonna song now in 2017, I feel like a bad person. I guess I’m not so much “down” on “Angel” as I’m just not “up” on it. Its fine, I guess. It has that 80’s pop sound that I didn’t care for at the time, but I can kind of get past that. When I make these lists, I establish a number of fixed goal-post songs. When I consider other songs, I ponder “do I like this one more or less than each of these goal-posts.” “Angel” is my “fine but I don’t really care all that much” goal-post.
78. Live to Tell
From 1986’s True Blue, First Single
Hmm. I’m really down on True Blue. One song from that album is in my top 40. No, not that one. That one is at 72. “Live to Tell” is a much-loved and much-respected Madonna single that I find ponderous. I think it has aged well for an 80’s ballad, respect her vocals and think this is one of her strongest lyrics. That said, there’s something about that whole “ding dong dong” keyboard line that just makes the song drag when I listen to it. I do like the Eno-esque keyboard break-down that resolves back into a verse. Sorry, True Blue. You probably deserve better from me.
77. Me Against the Music (Britney Spears featuring Madonna)
From Britney Spears’ 2003 Album In The Zone, First Single
OK, so, where to rank this song? Its a Britney Spears track featuring Madonna but I think its also an essential part of Madonna’s discography. Madonna has been accused of riding musical waves (as opposed to David Bowie who, you know, just rode musical waves) but I think listening to this song and contrasting it with the best song she released in 2003 reveals that Madonna was on a very different wave than Britney. This is a very good Britney Spears song and since I’m unlikely to rank her singles, let me take a moment to opine on the divine Ms. Spears. We don’t take good care of our pop icons, especially our young pop icons. Spears – perhaps more than any other living former-teen-star – has had her agency stripped from her (I don’t think she’s allowed to control her own finances to this day). She’s been treated as a commodity that generates money for other people and for the sin of being successful at what she does, she’s been ridiculed, worshiped, despised and treated like a thing instead of a person. Craig Ferguson hit the nail on the head when he explained why we shouldn’t be mocking her, but I’ll add that evidence points to the possibility that Spears has had very little say in career trajectory. I wish her health and peace and happiness and that she be treated with more respect than she’s been treated. Anyhow, this is a decent Britney Spears track and I like Madonna’s role in it as a sort of elder statesman of dance pop.
76. I Want You
From 1995’s Something to Remember, Song That Charted
I’m pretty down on Something to Remember, too. I loved Bedtime Stories (the album that proceeded it) and adore Ray of Light (ignoring Evita, the album that followed it) but found this album to be a sort of step backwards (sometimes literally, since many of the tracks were remixed of earlier ballads). This is a cover of a classic Marvin Gaye song and the single is a collaboration with trip-hop group Massive Attack (who I love). This is such a radical reworking of Gaye’s tune that its almost impossible for me to even hear them as the same song. While this tune has really grown on me in the last months, I can’t remember how it sounds five minutes after listening to it (I can remember the Gaye version pretty clearly, so this might be a matter of the original crowding out the cover). I can see myself playing this on a chill-out playlist with all the other Massive Attack songs in my library and enjoying it in that context quite a bit.
75. Who’s That Girl
From the Soundtrack of the 1987 film Who’s That Girl, First Single
OK, close your eyes, think of the Pet Shop Boys and press play. Ignore the vocals if you can. I can totally imagine Neil Tennant singing to this music in 1980. That keyboard line is rich and meaty. Now, when I started this project, I thought this and “La Isla Bonita” were the same song and was a little perplexed as to why they were two separate tracks. Turns out I just never really listened to them all that closely back in the 80’s and thought that when the background vocalists were singing “Quien es esa nina” that they were singing “La isla bonita.” I am appalled with myself. Anyhow, we’re still in the “meh” section of songs and I’m pretty “meh” on this one. Clearly, though, it doesn’t really stick with me.
74. Little Star
From 1998’s Ray of Light, UK Promotional Single Only
“Little Star” was released as the B-Side to “The Power of Goodbye” in the USA and seems to have been released both as a CD single and as a double A-Side with that song in the UK. Its also a trip-hop number and I think it might be about her daughter, Lourdes. Or maybe not. Like some of the other songs in this section of the list, it doesn’t especially stay in my head, but I enjoy listening to it well enough when its playing.
73. Rescue Me
From 1990’s Compilation The Immaculate Collection, Second Single
I’ve discussed this at length elsewhere, but for those of you just tuning in, I dislike the ancient practice of releasing a greatest hits album by an artist with one or two new tracks on that album. It essentially forces a fan to purchase a bunch of songs they already have just to make sure they have the new songs. Boo to all record labels. There were two new singles on The Immaculate Collection. One of them was a stone cold classic. The other one was “Rescue Me” which sounds like Madonna took some outtakes from other sessions and Frankensteined them together into a song. Like I hear hints of “Vogue” and “Justify My Love” in this song, but that might just be my tin ear acting up again. I think 15-30 seconds of the verses of “Rescue Me” would have made a great bridge or intro for a different song with the same chorus but the whole spoken word thing just doesn’t click with me on this one.
72. Papa Don’t Preach
From 1986’s True Blue, Second Single
I know, I know. I was just talking with my friend Shirley about this track today and she was relating to me how awesome this song is as a karaoke track. I have a lot to say about the song, but the short version is I have a ton of respect for it but don’t especially enjoy it.
“Papa Don’t Preach” is one of Madonna’s most important tracks. The violin stings at the beginning boldly announced that she was expanding her sound. The bass work is just great. The lyrics (which I just now learned weren’t written by Madonna) are provocative and fit well within her ouevre. While I like to think “Like a Prayer” was her great leap forward artistically, many of the elements I admire about that song are present on this track.
And let’s talk about the lyric (which were written by Brian Elliot with some minor contributions from Madonna). This is a quintessential “the personal is political” track. Critic Robert Christgau argues that she’s ambiguous about whether the song is antiabortion or not and that this ambiguity is a bad thing. I believe she’s not being ambiguous at all – the act of keeping a child is not ipso facto antiabortion. With the acknowledgement that pro-forced birth people embraced the song as backing their position, I would argue that the song is essentially pro-choice – she has the option to have an abortion but she’s choosing to keep the baby. That’s a choice and a major one that she’s making even though her friends (and presumably her father) are going to encourage her to make a different choice. Choosing to keep a baby is one of the available choices involved in being pro-choice.
Obviously, I could be completely wrong here – we all hear what we want to hear and I might be reading my opinions into the song. Madonna, as recently as 2009, was non-committal on this subject, focusing instead on how the song is about standing up to male authority figures – which is frankly another reason why the song was revolutionary for 1986 (and, sadly, is still pretty revolutionary now).
Anyhow, I admire the song so much that I listen to it closely whenever it plays. I just don’t enjoy the song very much. I’d initially ranked it much lower on this list but I really enjoy grappling with it even if I’m not likely to bust it out as a karaoke number. I’ll applaud you if you do.
71. Bye Bye Baby
From 1992’s Erotica, Sixth Single
Again, I like the message of this song (brushing off an abusive lover) but am not especially enthralled by the song itself. Madonna made the choice to sing this one in a sort of casual way – “I’m kissing you off and I’m already over you emotionally.” I can respect that choice both artistically and as a legitimate way to walk away from somebody – especially somebody abusive. The effect it has on me when I listen to the song, though, is that I find myself tuning out. I do like the beat, though, and have been known to trail dance to this song.
Coming Soon: Into the realm of the pretty good.