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.
My friend Shirley is now town for a few months directing Comedy of Errors for the Hawaii Shakespeare Festival. She, her family and I were walking down from Manoa Falls and discussing Madonna. Shirley had a ground-floor view of Madonna’s rise in the 80’s from the discos and dance clubs of New York City. I had always thought Madonna was from New York but it turns out she was originally from Michigan. This led me to read a bio on her and it turns out Madonna was a straight-A student who focused on dance. She lived the stereotype of the wanna-be performer who moved to New York City with $25 and a dream and then eventually broke through via hard work, talent, smart choices, determination and luck.
Anyhow, as I mentioned in the last entry, we’re already at the “I like these songs but I like other songs better” portion of the list so there will be a little less snark. Sorry, snark fans! I’m guessing 3-5 of these will seem to be ranked unconscionably low but Madonna has a lot of songs and they can’t all be Top Ten. Or Top Fifty.
60. Hold Tight
From 2014’s Rebel Heart, Fourth Single
This is Madonna’s most recent single so far and the first one (of four) on my list from Rebel Heart. The lyrics start with a paraphrasing of the Lord’s Prayer so it feels a part of her ouevre but in a way that doesn’t draw attention to itself like on “Girls Gone Wild.” I especially like the chorus on this song (particularly when it reaches the “Everything’s gonna…” noise noise noise part). Rebel Heart is Madonna’s worst selling album though this is at least in part due to the fact that fewer and fewer people are buying albums in general. None-the-less, the odds are reasonably good that you’ve not heard any of the songs from it. I encourage you to check some of them out – its one of her strongest albums this century, ranking up with the equally excellent Confessions on a Dance Floor.
59. Lucky Star
From 1983’s Madonna, Fourth Single
I was pretty sure I hated “Lucky Star” but it turns out its really quite a good song. This was one of the tracks by Madonna that was played a bunch on our local college station, WXCI, when I was growing up. Listening to it now, I am struck by how much it sounds like the other synth-pop songs that were getting airplay back then – it really did fit in with Depeche Mode, Heaven 17, The Human League, etc. Furthermore, her look at the time wasn’t too far off from some of the English bands I was listening to back in the day (though she made it her own and, furthermore, made it iconic). Had Madonna failed to find a huge international audience, I would probably be proudly playing this song on 80’s alternative pop playlists. So, basically, the only reason not to like it was because she had become popular. I suck. Anyhow, “Lucky Star” is still not my favorite Madonna song but its quite good.
From 1992’s Erotica, Fourth Single
This is a cover of a song by Little Willie John. Well, originally performed by Little Willie John, though maybe the best known pre-Madonna version was by Peggy Lee. Madonna’s version probably owes a little more to Lee’s – both feature a more restrained vocal than the original though Madonna’s strikes that great bass line from the Lee version and replaces it with a trip hop beat. On The Spot (my improv team) does this game where we get a beat going and then we try to sing existing songs to that beat. Its a lot of fun and sometimes you can make a song work perfectly. I’d always imagined Madonna was just fooling around like we do in the studio while a beat for another song was playing and liked the result. I’m overjoyed to report that this is exactly what happened. Happy accidents are the best accidents.
57. Bedtime Story
From 1994’s Bedtime Stories, Third Single
Bjork wrote this one for Madonna. Bjork is one of my all time favorite artists and I can’t wait to write about her singles. Consider this a warning. Anyhow, if you imagine Bjork singing this song, it makes a completely different kind of sense. Madonna takes the song in a more blissed-out direction than Bjork might have, at least in my imaginary version of Bjork’s take on the song. Its really good, that take. I wish you could hear it, but I only I can hear it. I’m going to jam out to that for a few.
OK, so, I dig trip hop quite a bit but its more of a chill-out experience for me than a let’s get up and dance experience. I should put together a massive trip hop playlist so the world can chill out. I confess, at my age, chilling out is usually followed by passing out. As in sleep. Like it puts me to sleep but in the best way.
56. Causing a Commotion
From the soundtrack to the 1987 movie Who’s That Girl, Second Single
This is my favorite track from the Who’s That Girl soundtrack. Lyrically, the song was inspired by her then-husband Sean Penn’s violent nature. What I really dig about the song is the bass work. I saw this film in the theatre (under some duress) and sort of didn’t care for it but I loved how this song sounded on the big speakers. Its a really exciting bit of music and if the rest of the song doesn’t quite live up to it at least its catchy.
2010 Fan Club Gift Single
“Broken” was recorded during the Celebration sessions but was not released as an official public single. Members of Madonna’s fan club received a 12” pressing of this single as a special gift. Thanks to the magic (?) of the Internet, we can all enjoy this song now. Its a fantastic song but I admit I feel just a little bit bad listening to it since it wasn’t Madonna’s intention that we non-fan club members hear it. She’s savvy enough to know that once she released it it would eventually be everywhere, but still. Madonna worked with Paul Okenfield to create a few new songs and this was one of them. For whatever reasons, they decided “Celebration” was the Oakenfield track that would make it onto the record and not this one. I sort of get it – Celebration was a greatest hits package and you don’t want to load it up with too many new songs (just enough to force the rubes to buy a bunch of songs they already have, har har har). On the other hand, “Broken” is an infectious song with a killer chorus.
From 2005’s Confessions on a Dance Floor, Fourth Single
Kris Kross, Van Halen, The Pointer Sisters, Flo Rida, and Rhinanna are among the other artists who have urged you to jump. Now Madonna is urging you to jump too. Why aren’t you jumping? What are you waiting for? House of Pain? Maybe its because we’re both older people now, but Madonna gets what kind of dance music I like (and what kind of dancing I can do at this stage – jumping). While lyrically this is a bit more like taking a risk on a relationship, I still think we should all be jumping. All the time.
53. La Isla Bonita
From 1986’s True Blue, Fifth Single
As I mentioned before, I thought this and “Who’s That Girl” were the same song. In my defense, the same production team worked on both songs. That’s some weak defense. In theory, this isn’t really the sort of song I’d typically like. If I were so inclined, I could find a lot to criticize. I am not so inclined and instead will report that singing along with the “Last night I dreamed of San Pedro” section is one of my life’s joys. Madonna’s music has, at times, been heavily influenced by Latin rhythms and themes. This was her first obvious foray into Latin music and she and her writing/producing team created a little masterpiece and one that I like quite a bit even if I like 52 of her singles even more.
52. Dress You Up
From 1984’s Like a Virgin, Fifth Single
Hey, I’m surprising myself. I was pretty sure that all of Like A Virgin would fall to the bottom ten before my inner 15 year old’s wrath. His hold on me has weakened enough that I can admit I really like a bunch of songs from that album – two are, in fact, in the top 50. Amazing! “Dress You Up” is, intentionally or not, a sort of reply song to “Material Girl.” In the latter song, she longs for a guy who has some serious cash. On this song, she goes more in the direction of “there are some things better than fancy clothes.” Specifically, her love is better than fancy clothes. She’s going to dress you up in it. It is possible there is a double-entendre at the heart of this concept.
51. Oh Father
From 1989’s Like a Prayer, Fourth Single
I love how free Madonna sounds on Like a Prayer. She hops from the overblown gospel dance sound of the title track to the psychedelia of “Dear Jessie” to the passionate ballad of “Pray for Spanish Eyes” to a few amazing tracks that we’ve yet to look at. There’s a lot to unpack in the history of this song and rather than doing it myself, I’m just going to direct you to the Wikipedia entry about it. Madonna’s vocal performance is one of her rawest and most honest especially later on in the song. The “father” in the title could both be interpreted to be Madonna’s actual father or God the father – the video supports both of these possibilities. Anyhow, its a terrific song and it lies at exactly the halfway point in my estimation because she has even more terrific songs.
Coming Soon: The song from Madonna’s best movie performance, for serious.