There's no denying Madonna's seismic impact on music. For nearly four decades now, she's been a trendsetter, shape-shifter, and innovator—a provocateur of pop and fashion and culture. But this is a double-edged sword. Because Madonna is so bold when it comes to her music, that means it's never safe. Translation? She's produced some brilliant songs…and some misfires. Oftentimes, these are intermixed on the same album, which makes listening to her work a very polarizing experience. Diehard fans get this. They know that one of her best tracks can sometimes be followed by something they feel is unlistenable. But I wouldn't have it any other way. Madonna's refusal to play by music's rules is one of the things I love most about her. The fact that she continues to push boundaries—even up to her most recent album, 2019's Madame X—is awe-inspiring. Because the thing is, when Madonna does make a hit, it's not just a hit: It's transcendent.
These 10 songs, below, are the brightest examples of that. I consider them to be the best in her discography, and you've no doubt heard many of them. Most of these songs are more than just dance floor-ready bops: They're real pieces of music history that will stand the test of time. As for her worst songs, which I've also listed? Well, let's hope we forget about those.
10. "Like a Virgin" (1984)
Madonna could have easily been a one-album wonder after her debut, but she followed it up with something the world couldn't ignore: a splashy, synth-y jam called "Like a Virgin," complete with a music video in which she wears a wedding dress. Pair this with a headline-making VMAs performance—where she rolled around the floor, also in a wedding dress—and you have one of pop's most potent moments. Ever.
9. "Music" (2000)
Following 1998's introspective, haunting Ray of Light album, Madonna went bright, colorful, and fun. "Music" is one of her most widely-celebrated tracks, with a sledgehammer chorus and fresh electronic production that could easily work on a 2020 Charli XCX record.
8. "Holiday" (1983)
There's no way this song couldn't make the cut. By far the standout on Madonna's debut album, "Holiday" is effortlessly joyous, with a chant-like refrain that never once feels cringe-y. It's pure light.
7. "Into the Groove" (1985)
"Into the Grove" may have been our first glimpse into the music Madonna would come to be known for: grimy club delights with just enough froth to make top 40 radio. The song sounds very much of its era, but make no mistake: It can still move a room of even the most unbothered millennials. I've seen it many times.
6. "Live to Tell" (1986)
Madonna isn't necessarily known as a balladeer, but her more downtempo moments shouldn't be overlooked. Exhibit A: "Live to Tell," a melodramatic shot of emotion that highlights her signature throaty vocals.
5. "Hung Up" (2005)
ABBA has only let one artist sample their music: Madonna, and thank God they did. No reinvention of M's is more beloved by fans than 2005's Confessions on a Dance Floor, a nonstop, wall-to-wall dance record that soundtracks like a night out. (On the original CD, there were no gaps in between the songs, so it literally played like a DJ set.) It kicks off with the shiny, disco-fied "Hung Up," which topped the charts worldwide. The track is Europop bliss: pulsating and primal, with a bridge that begs to be shouted from the top of your lungs.
4. "Express Yourself" (1989)
Madonna has always been a feminist figure, but that's presented perhaps most directly on "Express Yourself," a stomping ode to recognizing your worth. "Don't go for second best, baby," she exclaims on the thumping chorus, as shimmery bells and whistles swirl in the background. It's yet another example of M's impact on modern radio: There's a current wave of retro-sounding pop happening in top 40, and it all harkens back to "Express Yourself."
3. "Ray of Light" (1998)
When I used the word "transcendent" earlier, I had one song in mind: "Ray of Light," the title track off Madonna's most acclaimed record to date. Widely credited for helping drive electronica into mainstream pop, "Ray of Light" is an absolute rush of techno euphoria, a spinning, sparkly ode to the universe and all its wonderment. It's a song that doesn't just compel you to dance but feel everything around you, like ecstasy without the drugs. And you'll never want the high to end.
2. "Vogue" (1990)
Two songs are largely viewed as Madonna's most essential. This is one of them, and it's obvious why. It's a near-perfect dance tune, complete with easy-to-learn choreography and a hook that literally commands you to "move to the music." If one phrase could some up Madonna's discography, that would be it. Of course, the conversations around the accompanying video's appropriative nature are absolutely valid—and they've been argued at length many times—but there's no denying the omnipresence of this song, both in clubs and culture.
1. "Like a Prayer" (1989)
If, "Move to the music" sums up Madonna's discography, then "Like a Prayer" sums up her entire career. It was, and always will be, her sonic, artistic, and cultural climax, which is no shade to the albums that followed it. (Please see: Confessions and Ray of Light.) But there's something undeniably special about "Like a Prayer." Not only is the song a pop gem of the highest degree, the video—with its sexual and religious themes—set the stage for what Madonna would do in the next two decades. She would challenge how the world viewed Christianity and talked about sex—and the role women played in both those ideas. She would push buttons and piss people off but get them to have necessary conversations. That all started with "Like a Prayer." It really was groundbreaking, and its effects can still be seen and heard today.
10. "Illuminati" (2015)
Muddled, clunky production and lyrics about one of the 2010s biggest internet conspiracies make "Illuminati" a dated mishmash. It's a forgetful song on what's otherwise a wonderfully bizarre Madonna album (2015's Rebel Heart).
9. "Shoo-Bee-Doo" (1984)
The hook on "Shoo-Bee-Doo" glazes right past fun and heads straight to irritating. A word of advice from a Madonna stan: Skip this one and, instead, listen to "Angel," one of the best songs on the Like a Virgin album, a second time.
8. "Incredible" (2008)
This song clocks in at an unbearable six minutes and 20 seconds, but it's more than just too long: There's too much going on. The production on it is way too busy, which is saying a lot coming from me, an unapologetic supporter of Auto-Tune.
7. "Jimmy Jimmy" (1986)
Save for "Live to Tell" and maybe "Papa Don't Preach," everything on Madonna's True Blue album is airy, catchy, and exuberant. The only exception is "Jimmy Jimmy," which, unfortunately, took one step past exuberant and became…well, silly.
6. "Spanish Lesson" (2008)
Madonna's entire Hard Candy album was a bit of a misfire. It's clear she was chasing the 2006 sound of Justin Timberlake, Timbaland, and Nelly Furtado but a full two years later. The result is a collection of songs that sound stale and expired—and it's most apparent on "Spanish Lesson," a Latin-infused track in which Madonna equates sex and schoolwork. That's something not even the most devout Madge followers asked for. (The, "If you do your homework" bridge still haunts me.)
5. "Hanky Panky" (1990)
Madonna's Dick Tracy soundtrack album gave us many jewels, including "Vogue," but "Hanky Panky" is not one of them. All you need to know about this song is that it rhymes the word "panky" with "spanky." No further analysis needed.
4. "Give Me All Your Luvin'" feat. Nicki Minaj and M.I.A. (2012)
It's boggling to think Madonna chose this as the lead single for her MDNA album when she had certifiable bangers, like "Girl Gone Wild," waiting in the wings. The thing about "Give Me All Your Luvin'" is that it doesn't sound like Madonna. The cheerleader "L-U-V" chant at the top of the track is beyond cheesy, and the chorus never quite sticks. Not even a rapid-fire Nicki Minaj verse can save it.
3. "I'm Going Bananas" (1990)
Be glad this song, also from Madonna's Dick Tracy soundtrack, is under two minutes. It's a lukewarm attempt at salsa music that ends up coming off like slapstick parody, which is both problematic and hard on the ears.
2. "Hey You'" (2007)
Madonna's heart was in the right place on this one—it's a charity song released en tandem with the 2007 Live Earth environmental campaign—but the execution is…meh. Her acoustic songs, like the ones off 2003's American Life, are always best when paired with something avant-garde, like a weird electro effect or bass-line. "Hey You," though, just sounds like Madonna attempting to recreate "Imagine." And, well, you can imagine how that goes.
1. "B-Day Song" feat. M.I.A. (2012)
I'm sorry, but "B-Day Song" is truly unsalvageable. The MDNA bonus track is a lethargic foray into sixties twang that winds up sounding like grown-up "Patty Cake." To think this and the superb "Love Spent" exist on the same album is astounding, but like I said, that's just how Madonna rolls.
Christopher Rosa is the staff entertainment writer at Glamour. Follow him on Twitter @chrisrosa92.
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