The 10 best Madonna singles

Madonna - Truth Or Dare (


40 Years ago this summer, Madonna visited Seymour Stein, president of Sire Records (part of Warner Bros.), in the hospital with the desire to get a record deal. She succeeded, the deal was for the release of 3 singles, including an option for an album. The total value of the contract was $52,500, of which $7,500 would be made available if Madonna composed her own songs.


In the article on the great Ray Of Light album the start of Madonna’s career is already explained, so I’m not going to do that here again. Read the article Madonna – Ray Of Light.

Today, Madonna is the only out of three superstars of the 1980s, who were born in 1958, who’s still alive. Both Michael Jackson and Prince have left us.

Madonna - Artist Of The Decade - Billboard 12/09/1989 (

Madonna – Artist Of The Decade – Billboard 12/09/1989


Also, the successes are immeasurable. The advert above says it all really, and that’s the way it was on December 9th, 1989. By now, the total number of sold records has reached over 300 million! Madonna is the best selling female artist of all time. With 38 singles reaching the top 10 of the American charts, she’s the most successful female artist of all time.

Top 10

Madonna is responsible for a great number of excellent songs. So, now I give you my personal top 10 singles. The dates mentioned beneath the titles correspond with the dates of entry in the Dutch top 40.


Madonna - Holiday (


March 24, 1984

For me, Holiday was the first time encountering Madonna. I immediately liked the song. It was danceable, happy, catchy and well produced. After all this time, it’s still fun!

Madonna - Holiday (British version) (

Madonna – Holiday (British version)

The record company didn’t think the single would be as successful as it was, so no video was made for the song.

In 2005 Madonna named Holiday as her favorite single of all of her top 10 singles.

Sire didn’t want the Britisch single to include a photo of Madonna (and instead used a train), because they didn’t want the British audience to know that Madonna wasn’t an R&B (read: black) artist.


Madonna - Like A Virgin (

Like A Virgin

December 1, 1984

The first single off the album with the same name. Chic’s Nile Rodgers produced the album, which was recorded digitally, still a novelty at the time.

The video for the song was filmed in Venice and depicts Madonna singing and dancing on a gondola. She was also filmed wearing her distinctive 1984 outfit, white lingerie sporting the infamous Boy Toy belt.

Madonna on the lyrics:
“I like innuendo, I like irony, I like the way things can be taken on different levels.”


Madonna - Material Girl (

Material Girl

March 9, 1985

The song that defined Madonna, and the entire era. In the accompanying clip Madonna reenacts Marilyn Monroe’s performance of Diamonds Are A Girl’s Best Friend from the 1953 movie Gentlemen Prefer Blondes.

Madonna (about Like A Vigin and Material Girl):
“I liked them both because they were ironic and provocative at the same time but also unlike me. I am not a materialistic person, and I certainly wasn’t a virgin, and, by the way, how can you be like a virgin? I liked the play on words, I thought they were clever. They’re so geeky, they’re cool.”


Madonna - Into The Groove (

Into The Groove

August 10, 1985

At the time I had just started my study in Amsterdam and was introduced to a new phenomenon: cable television. The Into The Groove video was on every channel all day long, and the movie the song was linked to, Desperately Seeking Susuan, was heavily promoted. I loved the song. I watched the movie as well, which was quite enjoyable.

The song is infectious and is my favorite ‘early’ Madonna single.

“The dance floor was quite a magical place for me. I started off wanting to be a dancer, so that had a lot to do with the song. The freedom that I always feel when I’m dancing, that feeling of inhabiting your body, letting yourself go, expressing yourself through music. I always thought of it as a magical place – even if you’re not taking ecstasy. Hence that came to me as the primary inspiration for ‘Into the Groove’.”


Madonna - Papa Don't Preach (

Papa Don’t Preach

June 28, 1986

Best song off the True Blue album, that addresses teenage pregnancy. At the time this was a huge taboo. When Madonna played in Italy during her 1987 Who’s That Girl World Tour, she dedicated the song to pope John Paul II, who had called upon Itialians to boycot Madonna’s concerts, particularly due to Papa Don’t Preach.

“[The song] just fit right in with my own personal zeitgeist of standing up to male authorities, whether it’s the pope, or the Catholic Church or my father and his conservative, patriarchal ways… For ‘Papa Don’t Preach’ there were so many opinions – that’s why I thought it was so great. Is she for ‘schma-smortion’, as they say in Knocked Up? Is she against abortion?”


Madonna - Like A Prayer (

Like A Prayer

March 18, 1989

First single off the (fine) album with the same name. Once again, the single caused quite the uproar, in part because of the lyrics, but the large part was brought on by the accompanying video.

It’s hard to imagine now (although…), but several religious groups (including, again, the Vatican) called for a boycot. Not just of Madonna, but also of Pepsi and Pepsi related companies. One day prior to the video’s release, Pepsi had announced that Madonna had signed a $5 milion contract for advertising purposes. Under the pressure, Pepsi relented and forfeited the deal, with Madonna getting to keep the money involved in the deal.

And why? The story of a racially inspired killing, a black saint and dancing in front of burning crosses. The backlash reeked of institutionalized racism and (religious) hypocrisy.

“Once you’re a Catholic, you’re always a Catholic – in terms of your feelings of guilt and remorse and whether you’ve sinned or not. Sometimes I’m wracked with guilt when I needn’t be, and that, to me, is left over from my Catholic upbringing. Because in Catholicism you are born a sinner and you are a sinner all of your life. No matter how you try to get away from it, the sin is within you all the time.”


Madonna - Vogue (


Aril 7, 1990

If there’s one thing Madonna did was perfect at during her career, it was sensing the times. Madonna wasn’t the first artist to use voguing in music, but she most definitely was the one who elevated it to an international trend.

The classic, and beautful, clip was shot in black-and-white, and mimicked the 1920s/1930s era.

“I’ve been very inspired by New York. The song Vogue was inspired by walking into a nightclub and seeing the Xtravaganza crew voguing. And I was like ‘woah, what the hell is that?’. It was just the most amazing thing.”


Madonna - Justify My Love (

Justify My Love

December 1, 1990

The song was written by Ingrid Chavez (known for her involvement with Prince) and Lenny Kravitz. The song’s beat was a sample of Public Enemy’s Security Of The First World (which in turn was a sample of James Brown’s Funky Drummer).

The song, and the accompanying video in particular, were sexually explicit. Consequently, the video was banned by MTV. When the video was released on VHS it, almost overnight, turned into the best selling videoclip af all time.

“Why is it that people are willing to go and watch a movie about someone getting blown to bits for no reason at all, and nobody wants to see two girls kissing and two men snuggling?”

The Public Enemy sample was used without permission and Kravitz had claimed the song’s credits for himself. One year later a lawsuit, started by Chavez, resulted in adding Chavez’s name to the credits.


Madonna - Ray Of Light (

Ray Of Light

Msy 2, 1998

The title song of the phenomenal Ray Of Light album. A glorious electronic dance song, which keeps on building and building the suspense. One of the very best songs Madonna ever made.

“It’s totally out of control. The original version is well over 10 minutes long. It was completely indulgent, but I loved it. It was heartbreaking to cut it down to a manageable length.”


Madonna - Music (


August 12, 2000

Disco, electro-funk, dance? What does it matter. Music is a fantastic song, that addresses the influence that music can have on people’s lives.

In the video recorded for the song, Sacha Baron Cohen playes the role of his alter-ego Ali G.

Madonna about the inspiration for the song (in response to a Sting concert):
“Suddenly, people lost their inhibition and their politeness, and everyone was practically holding hands… I mean, it really moved me. And I thought, ‘That’s what music does to people’.”


For your listening pleasure, the playlist of the top 10 is displayed on the right.

In closing

What’s your opinion on Madonna? Do you miss songs, and if so, which ones? Let me know!

This story contains an accompanying video. Click on the following link to see it: Video: The 10 best Madonna singles. The A Pop Life playlist on Spotify has been updated as well.

Compliments/remarks? Yes, please!