This year marks the 30th year of Madonna singles. While the queen has fallen off some in the past decade, her legacy remains undeniable.
Here I present what I deem to be her twenty finest efforts (it shouldn't be hard to figure out what eras of hers I prefer). I'm ranking just the music here, not the videos.
20. Beautiful Stranger [1999]
This breezy, uptempo number was for the soundtrack to the second Austin Powers movie. Incorporating some 60s elements to tie into the film, it's groovy without being overly cheesy, and she taps into some of the energy she used on "Ray of Light."
19. Nothing Really Matters [1999]
Another cut from the ROL era, this song utilizes a hypnotic house beat to accent Madonna's then-new spirituality. It does so without being overly plodding or on-the-nose. Very light and carefree.
18. Take A Bow [1994]
14 years before Rihanna made (copied) an even more passive-aggressive version of this, Madonna created a more captivating and sensual ballad, the closing track to 1994's Bedtime Stories. It's a rather mature take on a conflict in a relationship, and it's easy to see (for the time period) why this was her longest-running #1 hit.
17. Sorry [2006]
The second single from 2005's Confessions on a Dancefloor continues not only the dance-fueled insomnia of "Hung Up," but also its lyrical bitterness. While that song focused on a relationship that was definitely over, this one is a bit more insecure, going for darker rather than triumphant tone.
16. Rain [1993]
The fifth single from 1992's Erotica, "Rain" is a rather metaphorical song (hint: rain = love). It's a very vivid simile that doesn't come off nearly as trite as it should. But what really sets this off though, is the smart dose of electronic flair in the production.
15. Miles Away [2008]
One of the only tolerable singles she's released since the Confessions era, this sounds like a lost FutureSex/LoveSounds track, but it also really fits Madonna's post-1998 sound rather well, and might be her only successful experiment with modern hip-hop.
14. Deeper and Deeper [1992]
The second single from Erotica, this is steeped in early 90s dance tropes, but like the content of the song, the music just seems to compel you forward. It also never settles into one exact groove for too long, keeping your attention in check for the entire length of the track.
13. Music [2000]
Possibly the catchiest bassline in Madonna's catalogue, this, the title track of her 2000 album, seems to give her presence a backseat to the beat at first glance, but it's really just a necessary adjustment to make the song work. And work it does, the synth hits contained throughout seem to have the power to stop time still for half a second at a time.
12. Express Yourself [1989]
Baby you were born this way. And you're fucking awesome.
11. The Power of Good-Bye [1999]
Living up to its name, this might be one of the most powerful tracks on Ray of Light. Also has some truly excellent production, subtle in all the right places. There just seems to be a bit more gravity to this track than most of her ballads, and it's exceptionally mature and intelligent.
10. Hung Up [2005]
After the commercially disastrous and critically mixed American Life, Madonna went back to her roots: uncompromised dance music. And it paid off, "Hung Up" is one of her catchiest and attention-demanding songs, and it provided her the smash single she needed to return to the public's good graces. A triumphant breakup song assisted by a killer ABBA sample, this could be the one late-period Madonna track that outlasts them all.
9. Bedtime Story [1995]
This song was cowritten the flawless Icelandic queen herself, Björk, and it's a clear indicator of where both Björk and Madonna would go with their next albums. It's ethereal, hypnotic, and utterly beautiful. Unfortunately, it failed to reach the top 40 in the US.
8. Like A Prayer [1989]
The biggest-feeling pop song of all time, and it just keeps getting bigger as the song progresses. It is absolutely undeniable in ways that few songs could ever hope to be; no mortal can resist succumbing to its power. It's probably not about black Jesus. At least not in that way.
7. Erotica [1992]
Right around the time that this single came out, Madonna put out a book titled "Sex." Of course she did. It featured Vanilla Ice posing with her while she was naked. Of course it did. Anyway, this track is similar to the earlier "Justify My Love," but it is far more commanding. This song is about fucking, not making love. With requisite vocalizations. It was one of the riskiest lead singles ever released, but thankfully it was a hit (thanks to the controversy) and sparked some discussion about sex in the media.
6. Vogue [1990]
Borrowing from drag ball culture (which is fucking fabulous and fascinating, please watch Paris is Burning on Netflix before you die), Madonna made a song that made everyone feel included in the dancing, without forcing anything. All backed by a sultry beat. Altogether one of the classiest dance singles ever released.
5. Ray of Light [1998]
A breath of fresh air. A five-minute trip into happy feelings and carthasis, dripping with acid synths and slick guitar licks, this was arguably the smartest of all of Madonna's reinventions, returning her to the status of the relevant superstar with "that new sound."
4. Secret [1994]
What initially appears as a stripped-down guitar track reveals itself to a hip, seductive, vulnerable song. It constantly evolves with some lovely melodic progression and continuously leads you on with its suspense. And delicious bass throughout.
3. Human Nature [1995]
"Oops, I didn't know I couldn't talk about sex." This is pretty directly a response to the Erotica/"Sex" era, and offers the queen at her most honest. Unapologetic, if you will. All over a west coast rap beat. Possibly grating, but "did [she] say something wrong?" No, she did not.
2. Justify My Love [1990]
A prelude to her next two albums, this track compels, rather than commands, sensuality. Accompanied by a very NSFW video, it remains one of the most unusual #1 hits in US history. But it's Madonna at her uncompromised sexiest. It's easy to get lost in this track, with its early trip-hop inspirations and whispers from seemingly all over. Hardly radio-friendly even over 20 years later, this song's success may be Madonna's biggest triumph.
1. Frozen [1998]
Hauntingly beautiful, this is Madonna's purest expression of love. Absolutely gorgeous instrumentals only help to highlight the selfless compassion exuded by the lyrics. There is very little I can say about this track because I truly believe it speaks for itself.
Honorable mentions
