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A whopping 12 Madonna songs reached No. 1 on the Billboard Hot 100. Some of those Madonna songs are all-time classics. On the other hand, one is a lifeless track inspired by William Shakespeare.

Madonna on a couch
Madonna | Koh Hasebe/Shinko Music/Getty Images

12. ‘Who’s That Girl’

The theme song for Madonna’s flop comedy Who’s That Girl somehow managed to reach No. 1 on the Billboard Hot 100. Why the American public bit on “Who’s That Girl” is anyone’s guess. This is one of the biggest Madonna songs that doesn’t get airplay anymore.

11. ‘This Used to Be My Playground’

Even an artist as interesting as the Queen of Pop made boring easy listening music sometimes. The strange premise of “This Used to Be My Playground” is ruined by a lack of musical momentum.

10. ‘Take a Bow’

“Take a Bow” has a reputation for being one of the great Madonna songs. Other than the cliche riff and the Shakespeare paraphrase (“All the world is a stage / And everyone has their part”), there’s nothing memorable about it.

9. ‘Papa Don’t Preach’

Of all the hit songs about teenage pregnancy, “Papa Don’t Preach” is definitely the best! In all seriousness, “Papa Don’t Preach” is a good illustration of why teenage pregnancy isn’t really a topic for pop songs.

8. ‘Open Your Heart’

“Open Your Heart” has a decent groove but Madonna arguably oversings the track. Asking someone to open their heart isn’t a bad idea for a song, but the Queen of Pop did it better in “Frozen.”

7. ‘Justify My Love’

“Justify My Love” is first and foremost a scandalous music video with a song attached to it. Still, it’s one of the most experimental No. 1 hits of the 1990s. Lenny Kravitz’s production is sleek and sexy.

6. ‘Live to Tell’

A good pop ballad is built around melodrama, and the riff from “Live to Tell” has more melodrama than an entire season of Dynasty.

5. ‘Vogue’

The 1990s saw the return of many 1970s trends. Madonna got to the party early by bringing disco back with 1990’s “Vogue.” Those opening strings are one of the club’s greatest siren songs.

4. ‘Like a Virgin’

“Like a Virgin” would be a tremendous bubblegum pop song, but the song’s tiny dose of sex makes it so much edgier and more memorable. Is “Like a Virgin” a beautiful love song or a sleazy novelty? You decide.

3. ‘Crazy for You’

Perhaps Madonna’s best ballad, “Crazy for You” combines desperation, sex, and some of the best backup vocals of the 1980s. So much of Madonna’s catalog is great dance music and “Crazy for You” is a perfect invitation to a slow dance.

2. ‘Music’

There are so many great rock songs about music. “Music” is the rare pop song about music and it has one of the best instrumentals of Madonna’s career. Sadly, Madonna never reached No. 1 after this, but what a song to go out on.

1. ‘Like a Prayer’

Behind the sacrilege, the controversial music video, and the scandalous live performances, “Like a Prayer” is simply a perfect song. If any song served as the Queen’s true coronation, it was this one.

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