Madonna Named Her 5 Most Iconic Songs and 2 of Her Picks Are Bad

Madonna named the five most iconic songs of her career. Three of the Material Girl‘s picks are correct. The other two are questionable at best.

1. ‘Like a Prayer’

During a 2015 interview with HuffPost, Madonna was asked to name her most iconic songs and the first she mentioned was “Like a Prayer.” Madonna’s career has been full of religious provocations and none was more sublime than “Like a Prayer.” On one level, the tune can be understood as a straightforward religious song. On the other hand, the track can be understood as a salacious pseudo-religious song about with some pretty strong innuendos. Regardless, it has one of the best instrumentals in the entire history of pop music.

“Like a Prayer” is part gospel, part funk, part pop, part rock, part ironic, and part sincere. In other words, it’s one-of-a-kind. Other pop artists like Lady Gaga and Lil Nas X attacked Christianity in their music, but none of them managed to write a song this perfect.

2. ‘Like a Virgin’

“Like a Virgin” also straddles the line between a joke and a heartfelt song. One could see it as a sweet love song about finding that special someone after suffering numerous broken hearts. In contrast, it could be interpreted as a naughty novelty song about virginity. Madonna resists being put in boxes.

Either way, the lyrics of the song are wonderfully ambiguous. While other ’80s dance songs were about simple subjects like dancing zombies and sussudio, “Like a Virgin” is so layered it inspires exegesis. Madonna’s helium vocals are the bubblegum cherry on top of a pop masterpiece.

3. ‘Ray of Light’

“Ray of Light” is an important song in the Material Girl’s catalog. It proved she could sing like no other when she put her mind to it. It also proved that she was capable of writing sophisticated 1990s alt-rock lyrics. But is it really as iconic as the Queen of Pop thinks it is?

Sure, “Ray of Light” has a great music video. However, it doesn’t receive as much airplay as other Madonna songs like “Holiday,” “Material Girl,” or even “Santa Baby.” “Ray of Light” is a lot of fun, but I doubt many zoomers have heard it.

4. ‘Express Yourself’

Madonna’s career had always had a girl power vibe, starting with the relationship protestations of “Borderline” and maturing with “Papa Don’t Preach.” “Express Yourself” might have been the first song of her career whose feminist theme was explicit. The opening line “Come on, girls! / Do you believe in love? / ‘Cause I got something to say about it / And it goes something like this” is a perfect rallying cry.

However, “Express Yourself” probably isn’t one of Madonna’s top five most iconic songs. Today, it might be more famous for its similarities to Lady Gaga’s “Born This Way” than anything else. Still, that funk beet is impeccable. 

5. ‘Vogue’

Now we’re back on track. “Vogue” isn’t just one of Madonna’s most iconic songs, it’s one of the most iconic songs of the entire 1990s. While much of the dance music of that decade sounds dated, “Vogue” has a retro sheen that makes it paradoxically timeless. The track’s campy rap number about Old Hollywood stars put Madonna on the same level as Marilyn Monroe and James Dean.

Madonna would explore house music again and again with tracks like “Rescue Me” and “Deeper and Deeper.” Those tunes don’t compare to “Vogue.” “Vogue” may have been the best house song to hit the mainstream until Beyoncé released “Break My Soul” decades later.