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.
Best
 

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.

Find out the worst songs at GLAMOUR