Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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Here it is. Are you nervous? I’m a little nervous. I’ve tried on five outfits, and my hair is just a fright, but oh my gosh, there’s no more time to prepare. Now is the moment. Here are my top ten Madonna singles of all time.

Okay, okay… one more stall. I want to thank everyone who’s been following this countdown. Your interest has made it even more fun.

Now it’s time. Let the countdown conclude.

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Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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Oooooo-weeee! We’re getting down to the wire, and everywhere you look, there’s a classic song demanding to be acknowledged. The next part of the countdown includes some of Madonna’s best-known work and two songs that should’ve charted much higher than they did.

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Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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Welcome to flavor country, people. The next batch of Madonna singles includes some undeniable classics and more hooky grooves than Captain Hook’s dining table. (Because he scratches it with his hook, thus making grooves. Ha! Wait… where are you going?)

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Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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For any other artist, this next batch of singles would be the highlight of a career. They’re all very good, and some of them are great… and when I consider that they’re not even in my top thirty, I’m reminded that Madonna is more than a “shrewd businesswoman.” People have called her that for years, and they mean she’s less an artist than a collection of successful strategies.

And while I would never claim that she’s the world’s best singer or songwriter, I submit these songs—her “mid-range” hits, if you will—as proof that she is much more than a CEO with a head mic. From producer to producer, from era to era, she has developed an excellent body of material that deserves to be respected as art as well as commerce.

Speaking of respect… I am totally stoked by all the “True Blue” fans who have written to insist that the song should have ranked higher than number 45. I had no idea it was so beloved! I’ll be interested to see what you think of the following. Remember, when someone has this many hit, some of them have to rank low…

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Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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Even though we’re at the low end of the list, we’re not really in trouble. Madonna’s least accomplished singles might be forgettable and derivative, but they are generally not unpleasant to hear. With a few ungodly exceptions, I actually like every song here… but like isn’t the same as love, you know?

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Welcome to Ranking Madonna’s Singles, in which I rank all 55 Madonna songs that have charted on Billboard’s Hot 100 chart.

To see all the entries in this countdown, just go here.

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Why am I doing this? Well, at this point, Madonna’s songs have been a constant part of my life for twenty-five years. In 1985, when I was six years old, I saved my allowance and bought the 45 single of “Material Girl.” Five years later, when I was walking past a neighbor’s house and heard “Vogue” coming out of the radio she kept on her windowsill, I knew I needed to hear that song again right away. The night before I went to Wal-Mart and bought the Like a Prayer album (on cassette!), I prayed for God to give me a sign if He thought owning Madonna’s music was a sin. At the time, she was making out with a black Jesus in a music video, so I felt like I needed to cover my bases. When I woke up the next morning without a bleeding dove at the foot of my bed, I figured the Lord wanted me to hear “Cherish” whenever I desired.

And that’s just the tip of the cone bra. In sixth grade, I frequently stayed in from recess to practice voguing. When I was an R.A. in college, I made it a hall-wide program to watch the premiere of the “What It Feels Like for a Girl” video on MTV. One night in 2008, I started refreshing my iTunes right at midnight, just so I could download “4 Minutes” the moment it was released.

Why does Madonna’s music affect me so deeply? Why do I hang on through every rise and fall in her popularity? Why can I remember exactly where I was when I bought Ray of Light?**

I’ll explore those questions throughout this list, and I’ll throw some serious gauntlets. Is “Don’t Tell Me” better than “Music?” Is “Crazy for You” a classic or a snoozer? Oh, my friends… I address all those burning questions and more.

Before I start ranking Madonna’s 55 Hot 100 hits, however, I want to praise her top album tracks. These songs were either never released or didn’t chart, but they still deserve a place in the Madge Hall of Fame.

**1998. Midnight. Tower Records in downtown Atlanta. My friend Brandt and I rode home from the release party in his silver convertible, blasting the song “Ray of Light” over and over.

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