Madonna turns sixty today, so Sam Brooks rounds up the best sixty Madonna songs to celebrate this with her.
Madonna follows forty-nine people on Twitter. I’m one of them. This is not a brag, but a fact. I have no idea why she follows me. I think it might be some algorithmic malfunction. But hey, facts are facts.
Madonna is also one of the most significant pop artists to have ever lived – potentially, the most significant single person in pop music history. I’m not here to debate that, because I don’t care what you think of Madonna.
What I’m here to do is give you sixty of Madonna’s best songs in her thirty-five-year career. Let’s not do the pre-amble, let’s jump in.
60. Dear Jessie
59. I Love New York
58. Dress You Up
56. Candy Perfume Girl
55. Love Spent
54. Keep It Together
52. Future Lovers
50. Veni Vidi Vici (feat. Nas)
49. Who’s That Girl
A semi-classic from the time when Madonna sounded like she was trying to be Selena before Selena was a thing, and her music was ripping off Janet Jackson. Nobody thinks of this song when they think of Madonna, but this mid-tempo Latin-pop song would be a star in anybody else’s catalogue.
47. Rebel Heart
46. Love Profusion
44. American Life
43. 4 Minutes (feat. Justin Timberlake)
The fake trumpets! The classic shifty Timbaland beats! An incredibly charisma-less performance from Justin Timberlake that hasn’t aged well and could have been done by anybody. Madonna caught Timbaland on the way down from his Nelly Furtado and Missy Elliot peaks but still managed to get a track that sounds fresh ten years later.
41. Girl Gone Wild
40. Human Nature
39. Impressive Instant
38. Deeper and Deeper
37. Me Against The Music (feat. Britney Spears)
This song happened, you guys. People forget about a lot from both of these artist’s careers – even though it’s a lean, roof-raising stormer of a track. Britney is basically rapping here, and when Madonna steps into the bridge with an almost Eartha Kitt-like confidence, it’s infectious. Also, this video played constantly on C4 back when they played music videos on network TV, and it likely has occupied a far too large part of my brain as a result.
36. Nothing Really Matters
35. Oh Father
34. Living For Love
31. Papa Don’t Preach
30. The Power of Goodbye
We don’t think of Madonna as a particularly notable balladeer because most people don’t think of her as a particularly good singer. This is an incorrect (and stupid) thought. Madonna is one of modern pop’s best interpreters, which I say with zero irony. Her instrument might be limited, but she injects her performances with humanity, wryness and personality in a way that only a true popstar and performer can do. When the production supports that, like William Orbit and long-time collaborator Patrick Leonard does in this song, the results are magical.
29. La Isla Bonita
28. Get Together
27. Nothing Fails
25. Drowned World/Substitute For Love
One of Madonna’s stranger and more proggy songs which somehow became a single. It’s one of many riffs on her own career and fame that she’s done throughout her career, but her voice takes on a girlish and youthful tone – as if recalling the artist she was fifteen years before this came out. The track has a beautiful build, it’s the kind of song that I can genuinely imagine Mitski releasing now. Like most of this era of Madonna, it was ahead of its time.
24. Express Yourself
23. Into The Groove
21. Crazy For You
20. Material Girl
19. She’s Not Me
Sticky and Sweet is not a highlight of Madonna’s career, but ‘She’s Not Me’ is a six-minute epic full of the fun and wit that signifies the best of her songs (as we’ll see below). It’s a song that manages to be about a cheating boyfriend cheating on someone who’s not Madonna, but also about an audience who expects Madonna to be any of the Madonnas that preceded her. If this was a single, it would’ve ended at about four minutes, but what we get after that mark is a pop-rock breakdown shredded for the gods.
It ends up reading like a challenge to herself. Madonna’s not Madonna, and she never will be.
18. Justify My Love
17. Burning Up
16. Like A Virgin
15. Die Another Day
This would, for what it’s worth, also be in my top three Bond themes (along with ‘Goldfinger’ and ‘Goldeneye’, don’t @ me). In 2003, Madonna was bringing us full-noise orchestra electro-clash, reinventing not only what a Bond song could be, but what a mainstream pop song could be as well. She barely sounds like Madonna on this track – she barely sounds human – and in the process, she basically sets the foundations for EDM to be a genre ten years later. But Madonna is no ‘feat.’ artist – she’s front-and-centre on this track, avoiding the cliches, suspending her senses, and dying another day.
14. What It Feels Like For A Girl
Still the best song to feature a Charlotte Gainsbourg vocal (courtesy of a sample from The Secret Garden, sorry Serge and sorry Charlotte’s own music which is very good). If you ever needed to disprove that Madonna is a great singer, this is the song I’d direct you to. Over William Orbit’s skittish beats and delicate synths, she breaks into her upper register and with each admission of humiliation, you feel her strength building up, right until that killer bridge closer: “When you open up your mouth to speak, could you be a little weak?”
13. Live To Tell
Like the below song, this was a tacked-on Oscar bid for a film that is barely remembered now. It’s the kind of epic full-noise song that you’d give to someone like Demi Lovato or Alessia Cara now, but unfortunately for them, Patrick Leonard’s not doing songs like that anymore. It’s a surprisingly mature and detailed song for something of this nature – it’s less about the end of a relationship and more about the childhood scars that lead to that and the lingering emotional trauma. It’s heady emotional stuff, and rather than being drowned out by the classically 80s production, Madonna’s vulnerability just shines through.
12. Beautiful Stranger
Ignoring for the moment, and potentially forever, that this was a song for Austin Powers 2, this William Orbit-produced ditty carries over a lot of the ebullient joy that Ray of Light had in spades. High reverb guitars, drum loops, and a catchy ‘da-da-da’ post-chorus turns it from an also-ran into a stone cold classic. The only reason why this isn’t known as one of Madonna’s best singles is record label douchebaggery (and maybe because it’s attached to Austin Powers 2).
Sometimes I have to explain a ranking. Sometimes I don’t. Holiday. Celebrate. The eighties was a dark time for a lot of music, but this is when all the production excess of the eighties shone in one holy direction to create one perfect post-disco pop single.
The less-famous A-side to Into The Groove, ‘Angel’ sounds exactly like what Carly Rae Jepsen would be putting out if she was around in the mid-80s. A sweet vocal, a straightforward but subtly dark production, and a beautifully earnest teenage approach to love that only the best pop can do.
9. Open Your Heart
Apocrypha states that Madonna heard this song – originally written as a rock song – and demanded that she have it. Sucks for the person who had it, but Madonna’s instincts were absolutely right. Very few people could sell these cheesy lyrics (“Open your heart to me, darling, I’ll give you love and you’ll turn the key”) with anything resembling honesty. The drumbeat doesn’t hurt, either.
8. X-Static Process
Okay, this’ll be one where you’ll go, “What the hell is that song? I’ve never heard of it?” It comes from the unfairly reviled American Life album (seriously, check it out, it holds up way better than you think) and it wasn’t even a single from that album.
It’s a simple song, one of the few in Madonna’s entire career which is basically just her voice and an acoustic guitar. When the first chorus kicks in, another guitar joins the mix, and she layers another vocal track on top of it – an incredibly literal showcase of self-doubt that works beautifully well. Either a song about her lover at the time or a song about her struggle with her faith. It’s an incredible deep cut of Madonna’s career, and an unfairly forgotten one.
7. Hung Up
Forget Mamma Mia and Cher singing ‘Gimme Gimme Gimme’, this is the best deployment of ABBA in the 21st century. There are three genius things in this pop song: the lyrics “time goes by so slowly”, the aforementioned sample, and the shit-your-pants drop 45 seconds into the song. She released this thirty years into her pop career. No questions on this placement, you guys.
6. Don’t Tell Me
The first time you heard this song, you thought your radio/stereo/music device was messing up, admit it. Madonna used a track skip in a pop song and then kept on using it. Another William Orbit classic that pretty much invented country-pop (not to be mistaken with pop-country, that’s Shania), this song is essentially Taylor Swift’s ‘I Knew You Were Trouble’ but ten years earlier and twenty years smarter.
Madonna is a mainstream pop artist who regularly puts out six-minute songs that become hit singles. It’s easy to forget that. It’s also easy to forget that sometimes these were quite weird and proggy slow songs that would sound more at home on a Sarah Brightman album than on MTV. ‘Frozen’ was Madonna’s first and bizarrely successful stab into world music with way more hooks than you’d expect for a song of this length. Madonna is bringing you Sorceress Edea realness in the video.
4. Ray of Light
Happiness is okay in pop music. We can allow it. You’re allowed to be happy for three minutes, singers. But relentless, ebullient joy? Nah, that’s not cool. Too much for us.
With ‘Ray of Light’, Madonna goes, “Absolutely not. Zephyr in the sky at night, dickshits!” This song isn’t a song that beats you over the head with how happy it is, it’s a song that drags you up into feeling better. I dare you to listen to Ray of Light and not feel a modicum better about yourself, the world, and the icon that is Madonna.
“Hey, Mr. DJ. Put a record on, I want to dance with my baby.”
This was the number one song in our country when I turned ten. That doesn’t mean much of anything, but I like to think it ties me to this club banger in some imperceptible, astrological way. In the same way that ‘Vogue’ did ten years earlier, ‘Music’ is a song that is way smarter and better than it has any right to be – it’s about enjoying music, it’s about getting to the club – and the song goes out of its way not to fall into a boring rhythm. The beat drops out entirely sometimes, it shifts into something else post-chorus, and there’s a random vocoder instrumental.
It’s the perfect club song of Madonna’s career.
I have been able to lip-sync the spoken word part of this song for the majority of my adult life.
We’re fifty-nine songs in you guys. If you don’t know why ‘Vogue’ is great at this point in your life, you’re lost to me and culture as a whole. Strike a pose, let your body move to the music, Dietrich and DiMaggio. If anything, this is the most famous example of Madonna drawing on underground scenes for mainstream success, and also the most commercially and creatively successful example of it – the fact that ‘Vogue’ is Madonna’s second best song is not shade on vogue, but it’s a testament to her career.
1. Like A Prayer
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How on earth do you write about ‘Like A Prayer’ which is, for my money, the best pop song to have ever been produced? On paper, it shouldn’t work: It’s a silly song about comparing loving God to loving a person. It has an ever-present choir in the background, the drums are kind of obnoxiously loud, and Madonna takes a backseat to an amazing gospel vocalist for the bridge for seemingly no reason.
But ‘Like A Prayer’ is the Sistine Chapel of music. You can marvel at its construction. You can wonder at how somebody could conceive of doing it, let alone actually achieve it. Or you can just sit back and let it wash over you, like the best pieces of art. It’s not about comprehending it, it’s not about understanding every moment. It’s about just experiencing it.
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