It only took a few minutes in the documentary The Greatest Night of Pop where Lionel Ritchie mentions that they had to choose between inviting Madonna or Cyndi Lauper, without being able to have both on the recording, for a new generation to wake up to one of the biggest sexist misrepresentations of so many decades: rivalry between the two biggest pop singers of the 1980s.

For teenagers who grew up in those times, antagonizing the two was expected, which was always a shame, after all, the two artists transformed the way girls dressed and behaved, but they were never on stage together.

Of course, Prince and Michael Jackson also had their beef, as mentioned in the same documentary, but, in pre-binary times, magazines and newspapers demanded the choice: either you were sexy like Madonna or you were original like Cyndi.

And the rivalry was reinforced with countless magazine covers that listed the differences between them. And yes, the two really can’t tolerate each other, but who could handle the pressure?

And behold, 40 years after they exploded, in 1984, both Madonna and Cyndi Lauper will perform in Rio de Janeiro in 2024.

A time machine and an opportunity to get closer? Well, the last part is unlikely. Let’s look at the most common points listed as conflicts between the Divas?

Style

Who came “before”? It’s a problem that fans of the two singers don’t know how to solve because the “thrift store style” of throwing several pieces on top of each other was the fashion of the 1980s, and both Madonna and Cyndi Lauper had this look as their “signature”. Both still think they came before the other.

That said, Madonna won the contest in a simple sense: what she wore could be copied by teenagers. The lace, the bandanas, and the bracelets were cheap and easy to find. Cyndi went for the somewhat more gypsy style of long skirts and high-top sneakers in different colors (still used today!) with fishnet stockings.

The problem? Every week she had one hair color, sometimes two in the same cut, and shaved one side. Impossible to imitate when at 14 or 15 years old your parents still determine the rules of the house, do you agree? In this way, wannabe Madonnas were more frequent than Cyndis.

What is sad, wrong, and regrettable is that on several covers and articles, the simplification of the comparison was that “Madonna was the most beautiful without talent” and “Cyndi was the ugly one, but talented”. Nothing more misogynistic!

Musical repertoire

Madonna’s music has always been seen by critics as “easy”, undoing her artistically and insisting that her success was the result of marketing and the cunning of exposure and controversy.

It’s hard to agree, but you can still understand the source of the cruelty. Cyndi Lauper, on the other hand, has always been praised as a songwriter and performer. In other words, Madonna was more ‘famous’, but Cyndi was more “talented”. Subjective as hell!

The main difference is that, although both are pop, Madonna opted for danceable songs with R&B sources.

Cyndi had a blues and punk streak that worked perfectly in the new wave years, but suffered when the style was considered “outdated.” In terms of chart hits, Cyndi took the lead in 1983, but when Madonna picked up the pace in 1985, she scored more number 1s.

Artistic quality

Although Madonna has always signed a large number of musical compositions, it was only after True Blue, in 1986, that it became clearer what her “music” was. Cyndi Lauper came with Time After Time – now an American standard – on her debut album, being covered by Miles Davis and other major artists.

I confess that I agree with this division: Cyndi has more voice, and greater range, and her compositions are ALL beautiful and emotional. You know when it’s her song, both because of the peculiarity of her accent and vocal style, while Madonna, eternal chameleon, doesn’t have a signature.

Activism

It’s a shame that the rivalry between Madonna and Cyndi Lauper prevented the two from always acting separately on feminist and LGBTQIAPN+ issues. Both embraced both causes even when it was not yet popular, they made a point of being bold in their videos, shows, and songs on topics considered taboo at the time.

Fame: True Colors or True Blue?

Madonna won this contest comfortably. She is still one of the most famous women on the planet and in the 1980s she was second only to Princess Diana in terms of paparazzi stalking and magazine covers.

Cyndi Lauper had health and personal problems that delayed the release of her second solo album, True Colors, released shortly after Madonna’s third, True Blue. That’s right, they both had albums titled True.

While True Colors mean showing how someone really is, revealing their true nature or character, True Blue expression is the definition of being unwavering in commitment and extremely loyal.

True Colors scored almost the same number of hits as True Blue on the radio, with Madonna briefly in the lead, but the covers of the politicized What’s Going On and Iko Iko suggested precisely a more engaged positioning of Cyndi, something that all the critics also used to collaborate with the beef between the two.

There is no “best” among them

I give my testimony in the first person as a passionate fan of both since I was 12 years old. There is no “better”, they are different and wonderful.

Many use the perception that Cyndi is smaller because she is more authentic, and Madonna’s chameleon side, one of her greatest qualities and the reason for her longevity, would have made her less original. Of course, we understand the analysis, but it is still subjective.

If we go into numbers and prizes it only gets more confusing. Cyndi has some of the most prestigious ones – Tony, Grammy, Emmy – just missing an Oscar. But her shows don’t fill stadiums like Madonna. Algorithms may give the Crown to one, but my loyalty is equally divided.

For 40 years I always dreamed of a collaboration between the two. Unfortunately, unlikely. But I’m glad they were always able to make me have fun. I love Cyndi! I love Madonna.