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Why Madonna Succeeded Where Cyndi Lauper Failed

Updated on October 30, 2016

Madonna and Cyndi Lauper appeared on the music scene around the same time in the 1980s. Madonna is still going strong and is still very well known. Lauper is still making music and peforming but isn't a household name. She's remembered for just a few songs. So, why is it that two artists who started out so big took such different career trajectories? And are there Madonna and Cyndi equivalents among today's major pop girls?

She's So Unusual Album Cover
She's So Unusual Album Cover
Madonna Album Cover
Madonna Album Cover

Record Sales

New Yorker Cyndi Lauper, born Cynthia Ann Stephanie Lauper, released her debut album She's So Unusual in 1983. The album produced four megahits Girls Just Want to Have Fun, Time After Time, She Bop, and All Through the Night. Her next two albums were also successes. Lauper went on to sell more than 25 million albums. Then she faded away. However, Cyndi is far from being a failure. She has worldwide record sales of 50 million and has won Grammy, Emmy, and Tony awards, which is a rare feat.

Michigan native Madonna Louise Ciccone released her first single in 1982 and is still a big name in music 30 years later. She's sold more than 300 million records worldwide. She's the best-selling female recording artist of all time according to the Guinness Book of World Records. Not only is she a successful singer, she's an entrepreneur, actress, author and director. She's become a musical icon and has influenced many of today's young female artists.

So, why did Cyndi Lauper fade away while Madonna continues to have commercial success and iconic status?

Madonna's Debut Everybody

Madonna Wanted Fame More

Madonna was business savvy. She was aware of the need to continually reinvent herself and her sound. She knew how to market herself. Cher said about Madonna:

...she is always riding the crest of the wave. She always saw trends WAY before anyone else...

Cyndi Lauper wanted to make the music she wanted to make. Not what happened to be hot at the time. Madonna was also willing to exploit her sexuality to gain attention in much the same way Miley Cyrus is doing today. She created controversy with her book Sex, which had explicit photographs and her explicit Erotica album. Madonna also courted religious controversy with her Like A Prayer video.

Lauper was far less controversial than Madonna, which would have meant less press interest in her. The most controversial part of her career was probably her song She Bop making the Parents Music Resource Center's "Filthy Fifteen" list because it was about masturbation.

Cyndi Wanted to Make Personal Music

Madonna didn't seem like she really cared about music. She wanted success and fame and the music industry was a means to accomplish that. This is not to say she didn't care about the music she made. She's a perfectionist who has strong visions for how she wants her albums to sound. But her albums were clearly made with a focus on commercial success rather than artistry.

Cyndi's debut Girls Just Want to Have Fun

Lauper was more of a true artist. She stubbornly wanted to make the music she loved and fought with her label for creative control. Madonna was a businesswoman who would follow whatever musical trends would sell.

Cyndi changed over time. She left her crazy, colorful image behind and started making personal music. This kind of music was less appealing to her younger fans and due to her earlier crazy pop girl image, she likely wasn't taken seriously by the kinds of people who would buy more serious music.


In the 1980s, it was common to see Madonna clones. Cyndi clones were a less common sight. Her image wasn't as attractive to young women and wasn't as easy to imitate. Just like how Katy Perry has a more appealing image to young girls than someone like Adele.

There was also an age difference. Cyndi was already 30 when she had her first hit. This made it more difficult for teenage fans to identify with her. She was already in her mid 30's when her third album came out. Madonna was only 24 when she first came on the music scene making it easier for young girls to identify with her.

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Album Breaks

Cyndi Lauper took big breaks between album releases. This is the release schedule for her first four albums.

  • 1983 She's So Unusual
  • 1986 True Colors
  • 1989 A Night to Remember
  • 1993 Hat Full of Stars

She also starred in the flop comedy film Vibes. In that same time period, Madonna released twice as many albums, starred in the hugely successful movie A League of Our Own and started her own record label Maverick Records. She was far more productive and always in the public eye. Cyndi was disappearing from the music scene for long chunks of time.

Are There Equivalents of Madonna and Cyndi Today?

The Madonna and Cyndi story is so compelling that people will look for comparisons with today's artists. California girl Katy Perry sometimes gets cast as a modern Madonna because she left behind her early pop rock sound to pursue commercial pop instead. And she's had huge success doing it. Many early fans felt she was a sellout. However, I don't think Katy has the level of ambition Madonna had. It's possible that she'll give up pop music at some point and transition to acoustic music where her real talent actually lies.

Katy Perry has said she wants to make an acoustic album someday

A more recent and much more Madonna-like example is Nashville born Miley Cyrus. She's using the same kinds of shocking techniques to gain publicity and it worked well for her so far. She successfully manipulated the media and general public to draw attention to herself. However, it's a bit early to cast her as today's Madonna because we don't yet know how she'll fare over the next few years. Time will tell if she's a worthy successor to Madonna.

Kesha and Lady Gaga are two artists who have fallen on hard times, so they are sometimes cast as the modern Cyndi equivalents. Kesha's excellent sophomore album Warrior and last two singles were major flops. Gaga's experimental (and to me disappointing) Born this Way album sold far less than her debut and produced fewer successful singles.

Like Cyndi Lauper, Kesha has a beautiful ballad that repeats the phrase "time after time"

Like Cyndi, Kesha Sebert (who like Miley is also from Nashville) is a true artist who stubbornly wants to make music she loves and is frustrated because she has to make radio friendly music. Instead of big names in pop, she brought rock legends and alternative artists onto her Warrior album as collaborators and she created a very artistic, noncommercial companion EP called Deconstructed. Kesha also fought her label Kemosabe Records for creative control.

Interestingly, Cyndi was the one who introduced Kesha's Die Young performance at the 2012 American Music Awards and both women have ballads that repeat the phrase "time after time" over and over. It's like she was destined to follow in Cyndi's footsteps. However, Kesha already made a comeback with her newest song Timber. She's working on her third album and she's filed a lawsuit to break her contract with Kemosabe.

New Yorker Lady Gaga (Stefani Germanotta) is compared to Cyndi because she had a massive era with her debut The Fame and a less successful but still very profitable era with Born This Way. However, her most recent lead single Applause struggled to get off the ground. She's since had flop singles and ARTPOP was a critical disaster. The Gaga comparison is understandable since she started off huge like Cyndi but then ran into trouble during her second album. However, she does have a massive and very devoted fan base. I don't see Lady Gaga going away any time soon because she has a large enough fan base to sustain her.

It's tempting to make these comparisons between today's artists and Madonna and Cyndi. The causes of Kesha's and Lady Gaga's troubles were very different from what happened with Cyndi. Many artists go through struggles in their careers and then bounce back. Time will tell if there really is a modern Madonna and Cyndi among us.

© 2013 Learn Things Web


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    • Ned 3 years ago

      Madonna was always a presence on the 80's and 90's music scene. Cyndi wasn't. I think long breaks were a huge factor in her fading over time.

    • Learn Things Web profile image

      Learn Things Web 3 years ago from California


      I do think the big breaks were a big factor. You can be forgotten very quickly.

    • Joel 2 years ago

      I love both.. I actually got to meet Cyndi twice and I've seen her 3 times. Madonna is "too big" to actually ever meet. Although since Kinky Boots Cyndi Lauper has gotten more of her fame back. Let's hope for a brand new album to help her out more.... oh and a collab ... how amazing would that be with the two of them on the stage singing TOGETHER.

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California


      Cyndi has definitely held onto her fame in terms of having respect and being able to continue to put out music and do plays and the like. Yet I think she doesn't have the downsides of fame that Madonna experiences from being too well known. It's great that you got to meet her multiple times and that she's so accessible.

    • Hector Ponce Cortegana 2 years ago

      Madonna has been with us for such a long time and she really knows what and how to do it!. Madonna will never stop making music.

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California

      Hector Ponce Cortegana,

      She really does. No one spots trends like Madonna. I can't even think of someone who matches her in today's music scene.

    • Tim 2 years ago

      That is why Madonna is reigned Queen of Music..but I still love Cyndi Lauer she was great in her time...

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California


      Yes, Madonna is considered to be the queen of pop and had a huge influence on female pop stars like Lady Gaga and Katy Perry.

    • Rayca 2 years ago

      Really well said. It seems like maybe the music execs. may know what's best. You have creative control, you don't sell records. The execs. know what sells. Really nice article.

    • But 2 years ago

      No one was a Madonna clone in the 80s they all copied Debbie Harry and Madonna did too. other than that great article !

      I think Gaga could have been a new Madonna if she didn't waste all her ideas at once. but she won't end up like Cyndi because her fanbase is just too big and too devoted (yet somehow can't seem to get her new album to platinum).

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California


      I didn't mean Madonna clones in terms of musicians. I meant there were a lot of fans dressing like Madonna but far fewer dressing like Cyndi. She didn't have an image young girls found appealing. I don't see Gaga being as big as Madonna but she isn't going away either.

    • kons 2 years ago

      Madonna's success it's a unique accomplishment...And that's bc Madonna's career/song/artistic existence has meanings (the right meaning at the right time)...No other artist had any kind of meaning (they were just singers who sang just songs) or if they later had, Madonna had it first. Madonna dared to speak about things that were huge taboos at the time, giving to people the chance to think. That's the reason. Beside that Madonna has a unique artistic way to pass these meanings to the people through her voice, her moves, her looks, her face.

    • jonthe1 2 years ago

      Madonna can't sing ,Cyndi can.

    • Treavor 2 years ago

      I don't get how you call Cyndi a failure when she is still in the industry and your still writing about her.

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California


      You must have missed this part:

      "However, Cyndi is far from being a failure. She has worldwide record sales of 50 million and she has won Grammy, Emmy, and Tony awards, which is a rare feat."

      But she is often seen as a "failure" in comparison to Madonna. I don't necessarily think this but their different career trajectories are often presented that way.

    • Alina 2 years ago

      I don't think age matters. there have been 20 something year old artist who were who did not become famous. and there is young people who enjoy artist who are past 30. nikki minaj for example. and 24 is a grown adult too so I don't get how that makes someone relatable to a teenager. that's more like justin beiber who was only 15 when he started.

    • Learn Things Web profile image

      Learn Things Web 2 years ago from California


      It's true that lots of young people listen to older artists. But most singers are in their teens or early 20's when they have their first hit and then their fans tend to grow up with them. Once those singers hit their early to mid 30's the next generation of teens will have moved onto the next group of young artists that break out. Radio is often reluctant to play songs from artists past the age of 35 because younger audiences find them harder to relate to.

    • Au fait profile image

      C E Clark 2 years ago from North Texas

      Interesting analysis and a good read. A shame women have to go to the lengths that Madonna and Miley have to promote their work. I think it's demeaning them and their audience demeans itself by expecting, requiring, and watching that sort of thing. It's more of a freak show than musical talent. People are so shallow . . .

      I couldn't answer your poll because I don't really care about either of them.

    • ANTONIO 21 months ago

      Beautiful analysis! add other observations: about the look I do not think that was less attractive lauper madona, rather I think the look of Madonna was more feasible to dress, how to prepare the lauper it would take a day!

      I think the lauper has weighed negatively wrestling in his image, and finally about to break album was unfortunately affects health problems.

    • Learn Things Web profile image

      Learn Things Web 21 months ago from California

      Thanks Antonio. Cyndi did have health problems that delayed her albums. It definitely wasn't a choice and it shows how outside factors can influence someone's career direction.

    • ANTONIO 21 months ago

      And about the choice of Cyndi for wrestling what do you think ?

      Greetings from Italy

    • Learn Things Web profile image

      Learn Things Web 21 months ago from California


      I know she was involved in wrestling years ago. I don't know if she's still doing anything like that.

    • Jessie 8 months ago

      I think both women are amazing! But when Madonna release her album in 1985 with Like A Virgin she became an instant Megastar. Even Cyndi can't match the "True Blue" album as Madonna's third. Whilst her (Cyndi) is deminishing in the 80s era alone. I think this concrete the statement of the author why Cyndi fails and Madonna became the "Artist of the Century" of the 80s alone which made MJ furious :)

    • Artist of the Century 8 months ago

      Artist of the Century

    • Absolutely cuntish 8 months ago

      You people are largely total fuckwits so shut the fuck up.

      YouTube Cyndi Money Changes Everything. .. choose the live version with about 1.3m views and get a dog up ya bcoz that there is a true star.

      No faked up phony slapper like Madge.

      A rock and roll pop angel at full tilt.

    • Jj 2 months ago

      I have problem with your definition of success. Madonna is a business, a perfect example of chasing the emptiness of fame and money. Cyndi and other artists are following their muse and found fame and $$$ along the way.

    • Justice 2 months ago

      Saying Madonna isn't an artist is wrong. She is an artist. She cared and still cares about her music. She was involved in music making and was willing to experiment.

      Just because she is a great business woman, doesn't mean there is no artistic integrity.

      She was good with trends. Not that she followed them, but she could have always sensed what will be huge.

    • Learn Things Web profile image

      Learn Things Web 8 weeks ago from California


      Madonna is definitely an artist. I meant true artist in the sense that she wouldn't have released music that wouldn't have been big on the charts.

    • Christian 7 weeks ago

      I think there's many back-handed "compliments" about Madonna in this article. More than a mere spotter of trends, Madonna is a phenomenally gifted songwriter and artist, always finding something new to say, always consistently good regardless of who she works with. And Madonna has certainly chased her muse as much as the best of artists - there's barely a genre of music she hasn't dabbled in. Rather than a trend spotter, I'd argue she is a bold risktaker whose gambles almost always pay off (except for American Life's war protest / folktronica). And she's the only artist who has had the stamina for a 30+ year career in the spotlight, with no breakdowns, no rehab and no playing the victim, even when the media and the public have been out for her blood. A legend of our times!

    • Learn Things Web profile image

      Learn Things Web 7 weeks ago from California


      These aren't backhanded compliments. They're objective observations. For me, I like their music equally. But it's obvious that Madonna did what it took to succeed in the mainstream while Cyndi didn't. I don't believe it's wrong to want to be a huge artist or a legend. But there's no doubt artistry has to take a backseat when someone wants to be a pop music phenomenon.

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