The Best Madonna Songs of All Time

No pop songs playlist would be complete without a showing from the Queen of Pop herself, the queer icon to end all icons, Miss Madonna Louise Ciccone. With a name like that, how could she possibly fail to become the superstar we all know and love?

Since her debut in 1983, Madonna has been a glittering beacon of individuality and (let’s not kid ourselves) an absolute go-to for karaoke nights and shower serenades. And with 19% of Grindr users naming music as their top hobby, it’s clear this playlist is especially relevant. So without further ado, we present 42 of the best Madonna songs that have had us singing into our hairbrush microphones for decades.

1. “Holiday”

We dare you to try listening to this without feeling a burst of joy. “Holiday” is an upbeat song about peace, love, and celebration — the perfect soundtrack for Pride.

2. “Lucky Star”

A funky tune that's sure to get your hips shaking. Released in 1983, “Lucky Star” gave listeners a preview of the megastar Madonna would soon become.

3. “Borderline”

Let's step back to the early days when Madonna was just a rising star. This tune, sweet as bubblegum and sassy to the core, is the ultimate ’80s jam.

4. “Material Girl”

Sappy slow dances are for middle school. What really turns Madonna on is cold, hard cash. Let's be real — we're all material girls (and boys) at heart.

5. “Like a Virgin”

No one, and we mean NO ONE, could forget Madonna writhing in a wedding dress at the VMAs. It's a classic that made parents gasp, teenagers cheer, and all of us wish we could feel like a virgin again.

6. “Open Your Heart”

Madonna’s blend of sex appeal and empowerment is on full display here, making our hearts go boom!

7. “Papa Don’t Preach”

Daddy, Madonna ain’t a little girl anymore. She can choose what she wants to do to (and with) her body. Drama, teenage rebellion, a seriously catchy tune — this song’s got it all! It's basically a soap opera in four minutes.

8. “Love Don't Live Here Anymore”

Even Madonna knows what it means to feel jaded. But instead of just making herself into a blanket burrito like the rest of us do when a once-happy relationship falls apart, this powerhouse songwriter turned her sadness into a tune we’ll never forget.

9. “La Isla Bonita”

Inspired by the many beautiful Latinos she encountered in New York City during her formative years, “La Isla Bonita” (Spanish for “the beautiful island”) spells out the details of a spicy fantasy that most of us encounter at least once in our lives — falling madly in love on a tropical isle. Pass the sangria!

10. “Like a Prayer”

It's not a party unless "Like a Prayer" pipes through the speakers. With a slow start and a beat that quickly picks up speed, this controversial track almost gave the Vatican a collective heart attack, but it became a defining moment in pop history. 

11. “Express Yourself” 

Madonna has shared many words of wisdom with the world, but the message in “Express Yourself” is one of our favorites. Be true to who you are, and if the person you’re with can’t get behind it, it’s time to move the hell on and find someone who will. It’s all about demanding respect and equality. Preach, girl!

12. “Vogue” 

“Vogue” is the song that took the underground art form of voguing mainstream. And while some of the OG queens might resent Madonna for that, we give her a lot of credit for helping the community feel not just seen, but imitable. Strike a pose, darling!

13. “Dress You Up”

For the drag queens and fashionistas among us, a tune dedicated to the pure art of dressing up.

14. “Deeper and Deeper” 

On the surface, “Deeper and Deeper” is just another song about sex. But the deeper you go, the clearer it gets that Madonna is telling the story of a young man coming to terms with being gay.

15. “Rain”

Water holds a powerful place in the art of storytelling. And on the fourth single from Erotica, which easily scored a spot on the Billboard Hot 100, Madonna imagines an AIDS epidemic-era rain so strong it will “wash away my sorrow, take away my pain.”

16. “Beautiful Stranger”

An Austin Powers-approved hit! Even international men of mystery can't resist a Madonna jam.

17. “Secret”

It’s mysterious, sultry, and irresistible. A secret we all want to know.

18. “Take a Bow”

Carly Simon’s “You’re So Vain” isn’t the only breakup song about Hollywood heartthrob Warren Beatty. This ballad is for the slow dancers, the love-struck, and anyone who knows what it’s like to have to say goodbye to a lover when what you really want to do is say hello.

19. “Into the Groove” 

If this song inspires you to pull out your best dance moves, you’re far from alone. And that’s the whole point of “Into the Groove,” which encourages listeners to dance and express themselves through music.

20. “Crazy for You”

Slow dance, anyone? When Madonna gets romantic, she gives us gems like this.

21. “You’ll See”

If a broken heart’s got you down, queue up “You’ll See” for a reminder that Madonna don’t need no man — and neither do you.

22. “True Blue”

This feel-good track is an ode to true love, and we’re so here for it. 

23. “This Used to Be My Playground”

Music may be the first thing that comes to mind when we think of Madonna, but this bitch has acting chops too. Next time you’re on a Queen of Pop kick, add A League of Their Own to your must-watch list. The film gave us some great quotable lines (“There’s no crying in baseball!”) and some great music, like “This Used to Be My Playground.” 

24. “One More Chance”

Ever lost a great love because you took him for granted? Hey, Madonna can relate. Sometimes you’re lucky enough to get one more chance with the wisdom to appreciate what you’ve got.

25. “I’d Be Surprisingly Good for You”

Next up on Madonna movie night? Evita, the iconic film that taught us a lot about Argentine history, made us drool over Antonio Banderas and gave us a handful of Andrew Lloyd Webber earworms like this duet with Jonathan Pryce.

26. “Don’t Cry for Me Argentina”

The most memorable line from Evita comes from the movie’s most memorable song, “Don’t Cry for Me Argentina.” Madonna may be telling you not to cry, but you’ll want to keep the tissues handy for this one. And when you’re done weeping, queue up the remix, which Madonna spearheaded with the goal of making the song more danceable while holding onto its emotion and Latin roots.

27. “Ray of Light”

When baby Lourdes was born, Madonna went through a bit of a rebirth herself, seeking answers to questions she hadn’t faced before bringing life into the world. “Ray of Light” is about Madonna's newfound interest in spirituality and the Kabbalah, but don’t let the serious subject matter fool you — this existential bop will have you shaking your ass.

28. “Frozen”

Madonna did it before Disney, giving us a mystical masterpiece about the coldness of love. And the icy aesthetics in the video? We get shivers just thinking about it.

29. “Music”

The ultimate road trip song, with a cowgirl hat-wearing Madonna that makes you wanna yeehaw your way to the dance floor. This upbeat dance-pop song is all about the power of music and dancing to bring people together.

30. “American Pie”

Don McLean’s nearly nine-minute folk-rock hit gets a Madonna reboot that clocks in at a much more modest four-and-a-half minutes. And she makes it danceable like only a Madonna song can.

31. “Die Another Day”

Madonna dips her toes into the Bond universe for this explosive track, playing the ultimate Bond girl in the sizzling music video.

32. “Hung Up”

Remember the days of waiting around the phone for that special someone to call? If you’ve ever been left on read, you’ll relate to this one. Sampled from ABBA's "Gimme! Gimme! Gimme! (A Man After Midnight)," this infectious track made us all disco divas again.

33. “Cherish”

Another ’80s Madonna song that’s pure pop gold. It's like a sunny day in song form.

34. “Sorry”

Even Madonna makes mistakes, but she’s a big enough person to offer up apologies. Keep this one on hand for the next time you need to say you’re sorry.

35. “Living For Love”

We live for this heartbreak anthem that had us all believing in love again. And that red matador outfit in the music video? Work it, queen!

36. “Give It 2 Me (feat. Pharrell)”

Madonna teams up with Pharrell Williams for this energy-packed dance anthem.

37. “Isaac”

The Queen of Pop’s appreciation for other cultures and religions shines through in “Isaac,” which features portions of a Yemenite Hebrew poem. A group of Israeli rabbis called the song blasphemous, but we think our goddess nailed this one. 

38. “Justify My Love”

It was so raunchy, MTV banned the video. Now, it's a classic Madonna banger. How’s that for justification?

39. “Don't Tell Me”

Madonna goes country, and honestly, it's a look and a sound that works.

40. “4 minutes (feat. Justin Timberlake and Timbaland)”

Madonna and Justin Timberlake on the same track? Yes, please! A dynamic duo for a dynamic apocalypse song with next-level vocals from our queen.

41. “American Life”

Madonna's take on the American Dream is as controversial as it is catchy. Would you expect literally anything less?

42. “Ghosttown” 

Another apocalyptic bop, “Ghosttown” imagines life for the survivors of the end of the world. Written as a callout to the intolerance and antisemitism Madonna saw taking a foothold in Europe, this song serves as a warning of what the world may become if we don’t get our shit together and start spreading love. But true to form, she delivers a serious message with killer vocals and a danceable beat.

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