My understanding is that the two of them came on the scene at about the same time. Why did one get single-name-famous and one didn’t?
I think Madonna had/has infinitely larger range of styles the Cyndi ever dreamed of. Madonna also continuously adapts herself and revamps her whole image ever few years. She is constantly striving to stay current. Think about Lady Gaga, now think about who will replace her in 5 years, and 5 years after that, and 5 years ago etc… Those were all Madonna.
Also, Madonna was a better singer and I’m willing to bet (having never seen either of them live) that she has a much better stage presence and probably puts on a better show.
Sex appeal.
Hers did very little for me, but it was there, and Cyndi Lauper’s wasn’t.
The drive. Madonna worked tirelessly from late 1982 to 1988 - in that period she was either releasing an album, or a single, or a film, or was on tour, or doing something to keep the attention on her and her work. 1988 was her year off and then she went straight into it again right through until she had her first child in the late nineties. And with every album there was a new image, a new development, a slightly advanced or changed sound.
Cyndi, by comparison, left three years between her debut and the follow-up, and then a further three years between her second and third albums. This wouldn’t necessarily always be a bad thing and she did okay, but compared to Madonna she was just left behind. Eventually Cyndi’s American success faded and although she’s done well for herself and is now regarded as an eighties legend, Madonna just outdid her as a pop star in every way imaginable. Madonna is on another level entirely.
I think they’re both amazing, just in different ways.
Most of what you said I agree with, but Cyndi Lauper is a much better technical singer than Madonna. Lauper had command of about 4 octaves, and Madonna’s voice, while capable, was limited and not particularly strong.
I heartily dispute this. Of the two - Cyndi has much more raw talent than Madonna. While Lauper has a thick Nooo Yawk ayyyccent that hampered her appeal, Madonna (especially in the early years when the two were in competition) has a rather thin, reedy voice. Madonna’s singing is heavily doctored in the studio and live recordings of her are barely listenable.
Madonna is the archetypal case study in how MTV changed the pop culture landscape - the image of her strutting around in the “Like a Virgin” video mattered far, far, FAR more than anything any actual singing she did. The music was almost beside the point.
Let me state for the record that I’m not anti-Madonna, I like her and even like some of her music, but as for why she ascended to super-stardom and Lauper became a “where are they now?” It’s purely iimage - Lauper’s stage personae perfectly represented a very specific time period in pop history - 1983 - while Madonna was shrewd enough to keep looking ahead, anticipating all the next pop culture trends and capitalizing on them.
Madonna is a business woman who can sing and dance. Cyndi Lauper was a performer who could sing and dance.
I don’t know what “single-name-famous” has to do with it. Madonna billed herself as Madonna, so she is known as Madonna. Cyndi Lauper billed herself as Cyndi Lauper, so she is known as Cyndi Lauper. If she had billed herself as just Cyndi she would be known as Cyndi to this day, just as, say, Jewel (certainly never as big a star as Madonna) is known as Jewel. Lulu was always known as Lulu, and Donovan as Donovan, for the same reason. The only example that springs to mind of someone who billed themselves by their full name, but is often known just by their first, is Elvis, and that surely has as much to do with the fact that his first name is (or was, when he first became known) very unusual and distinctive, as with the extent of his fame.
Not to disagree with the rest of your post, but Madonna was NOT the better singer when they both started out. Compare “Time After Time” with the comparable ballad “Crazy for You.” Madonna wasn’t too proud to get singing lessons, as part of her constant reinvention, and became much better as a singer over the years. (according to this Spin interview, she got vocal coaching for “Evita”, that would have been around 1994-95, and prior to that was very aware of her vocal limitations) However, she had always been a good performer – Madonna’s early training was as a dancer, not a singer – and later became a great performer.
I’d have to agree that sex appeal had a lot to do with it. Madonna was a beautiful young woman and she used it. Cyndi Lauper wasn’t ugly, but you’d think of her as quirky before sexy.
It’s not just that, of course; it’s also true Madonna was the hardest working woman in show business, and had a marketing savvy unrivalled in pop music. But sexy matters.
Madonna was blessed with good health.
Cyndi Lauper has suffered numerous health problems. It’s often prevented her from touring.
I think Cyndi is a better musician. But, her image has changed little since the 80’s. Madonna is a master at reinventing herself every few years. Keeps her fresh and up to date.
Organized Crime backing, (not that there is such a thing of course).
or
Perhaps wrestlers pinned her career down.
I like them both tho.
I hate to disagree with someone who’s agreeing with me, but I don’t think of Madonna as beautiful. Sexy, yes. Hot as hell, yes. But beautiful? Not on her best day. The most I can say for her looks aetheitically is that with a world-class production team of make-up artists and photographers, she can fool you into finding her quirkily attractive.
To me, her quintessential role is of the skanky, sexy Susan in Desperately Seeking…, drying her armpits on a hot-air blower in the Port Authority, and brimming with all the confidence in the world. Magnetic, but not remotely pretty.
Cyndi on the other hand always looked like your weird-duck loopy cousin with a great voice but you’d never find her pretty or sexy, just talented.
The OP makes the assumption that both women had the same aim, namely to become as famous as possible for as long as possible.
For Madonna I would tend to believe that. Now without suggesting that Cyndi Lauper was completed uninterested in fame, she always came across as being more about expressing herself without necessarily only aiming to sell as many records as possible.
There are many many people with more talent than Madonna who sell much much less than she does. Doesn’t mean they do not “have” something, rather than that their aims are different.
Madonna started a whole new marketing concept. A woman who wasn’t ashamed of her sexuality and used it as an asset. The strategy was to put something out there that pushes the boundaries of sexuality, get old and boring people riled up, and teenagers of course will love anything that old and boring people hate. It was later perfected by Britney Spears, and since then there has always been at least one successful female pop singer using the concept. Currently it’s Katy Perry.
Before Madonna no female singer really used the “I’m a sexy and proud of it” concept to sell music. Now advertisers use it whenever they can to sell anything to young adult women and teenagers.
The theme ran not only through Madonna’s music, but through every thing Madonna did herself. That’s why she was more successful than anyone else.
Popular music is never about the music. It’s about what the music says about the people who buy it. What do you think of someone who owns a Lauper record versus someone who owns a Madonna record?
In the sage words of Yogurt, Moichendising!~
(Spaceballs reference)
She was a far better business woman and new how to image herself as a hot commodity. She is extremely driven, add a little talent, and a lot of style and you have an icon.
Cyndi’s newest album is ten times better than anything Madonna has released lately.
Cyndi recorded with B.B. King, Charlie Musslewhite, and Johnny Lang. 
Some of the Best blues singers still living.
Memphis Blues is a must have in your collection.
One of the sadder moments I’ve heard on the Howard Stern show was when he had Cyndi on.
She sang a remake of “Time After Time” that wasn’t very good at all. And this was YEARS after the song became a hit. It was like she couldn’t come up with anything new so she remade her hit song from long ago.
Howard was nice to her, but the whole thing was pretty sad,
For your enjoyment:
Well, I enjoyed it at least.
OK, it’s Cyndi Lauper. Figure someone will want to know before clicking.