Cyndi Lauper on fun, fashion and freedom of expression: ‘We have braces on our brains’

Before Cyndi Lauper rose to fame as one of the most singular pop breakouts of the 1980s, she was queen of the cash register at the edgy Manhattan boutique Screaming Mimi’s. The vintage emporium is still a downtown staple, but a little of its spirit comes uptown this month with Cyndi Lauper: A Suitcase of Memories, a two-part auction of her fashion and personal items at the New York auction house Bonhams.

On a recent Thursday morning in New York, the singer is sporting seafoam green hair and is in good spirits as she leads a private tour of the collection. It is an Aladdin’s cave of outfits from her five-decade career, with clashing prints, jutting tutus and statement headwear in every color you can imagine. As she strides around in her platform creepers, she gives a few final notes to the Bonhams team. Is that rainbow fan at the right angle? And can we confirm that more mirror balls are on their way?

“Over there is my grandmother’s pyjamas,” she says, walking over to a mannequin that displays the leopard print sleepwear Lauper wore in the Girls Just Want to Have Fun video. The ensemble was originally purchased from her family’s favorite mail order catalog. “Frederick’s of Hollywood gave people in Queens a glimpse of glamor and sexiness,” she says. “You know, they’re flannel pyjamas, but come on – they’re leopard!”

Lauper’s leopard print pyjamas from the Girls Just Want to Have Fun video, 1983. Photograph: Courtesy of Bonhams

Born in Queens, Lauper was raised as part of a large family who worked in New York’s Garment District as cutters and seamstresses. After leaving home at the age of 17 armed with not much more than a toothbrush and a copy of Yoko Ono’s book Grapefruit, she honed her eclectic style while working at Screaming Mimi’s in between singing at downtown local clubs.

“I went to art school but I didn’t finish,” Lauper says. “So what happened is this, I guess.”

Lauper captivated a generation with performances which combined music with art and fashion, selling more than 50m records. Her fantastic debut She’s So Unusual became the first debut album from a woman to produce four top-five singles upon its release in 1983. Hits like True Colors and I Drove All Night followed, as well as new ventures: she co-founded the True Colors United foundation in 2008 to benefit homeless LGBTQ+ youth and, in 2013, won a Tony award for her Kinky Boots score.

Cyndi Lauper. Photograph: Greyshock. Courtesy of Bonhams

After retiring from live performance last year, Lauper says she is enjoying the chance to take stock. Leading us past the metal bra and headdress from her True Colors video and a red plaid dress she wore to the inaugural VMAs in the early 80s, she seems nostalgic for the freedom of the decade. “It was a time where there was a little bit of a wildness,” she says. “We’ve been corporatized – we kind of have braces on our brains. You know, it would be nice if you could think for yourself sometime.”

As well as ephemera such as handwritten lyric sheets, the exhibition features a Raggedy Ann doll from the Girls Just Want to Have Fun video and a multi-colored spotted couch that could have come from the set of Pee-wee’s Playhouse. “I did this to inspire people,” Lauper says of the show. “To inspire us who are older to remember the individuality of creativity, and to inspire the young to discover that creativity is individual.”

Lauper is a great storyteller – I could listen to her anecdotes for hours – and as no-nonsense as you might expect from a born-and-bred New Yorker. As we admire the singer’s newspaper skirt from her True Colors album art, a guest asks Lauper if she worried that the fragile-seeming skirt would fall apart. “What do you mean? No,” she replies crisply. “It was a photoshoot. I was good.”

Lauper’s newspaper skirt ensemble from the True Colors album cover shoot. Photograph: Courtesy of Bonhams

Last year, Chappell Roan wore a replica of the newspaper skirt while inducting Lauper into the Rock and Roll Hall of Fame. Lauper says that Roan is the one of the few current stars whose creativity she relates to.

I can see that with Roan’s edginess and use of color. “It’s not just that,” Lauper tells me in a conference room later that morning, adding that she sees songs like Pink Pony Club as landmarks for LGBTQ+ representation. “It’s how she wrote about a lifestyle and made it normal. And then the clothes, sure.”

In 2022, Lauper released a new version of her abortion rights song Sally’s Pigeons to protest against the US supreme court overturning Roe v Wade. “If we don’t have control over our own bodies then we have no real freedom,” she said at the time. “We need to mobilize. We need to let our voices be heard.”

She sees the exhibition as coming at a “great time to have people inspired and come alive again” as the midterms approach. Despite gentrification squeezing out artists from the city, she says “the good news is that, because of Mamdani, the billionaires might be moving out, giving us our city back.”

In 2023, Lauper gave her blessing for Nicki Minaj to sample Girls Just Want to Have Fun in a song from Minaj’s Pink Friday 2 album; Lauper joined her on stage for a performance a few months later. Given Minaj’s recent alliance with Donald Trump, does she feel differently about the collaboration now?

“No,” Lauper says flatly. “First of all, I don’t believe in cancellation. And second of all, the fact that she did Girls Just Want to Have Fun musically – it’s a political thing anyway, babes.

“Girls just want to have fun. They’re entitled to a joyful experience in this world. Like it or not, we’re here. We’re not going out in the rice fields any more. Yes, rise up and put your foot down, and she did. I don’t know what she’s doing now. But I still don’t think you cancel people, because otherwise there’s no room for discussion.”

Cyndi Lauper. Photograph: Ruven Afanador / Courtesy of Bonhams

Lauper says that she learned the importance of breaking bread with those across the political spectrum through her advocacy work. “If you want people to listen to you, you need to listen to people,” she says. “If you don’t let people evolve, what are you doing?”

The exhibition shows how Lauper’s own tastes evolved too. In the 90s, she became increasingly drawn to sculptural pieces from Vivienne Westwood and Alexander McQueen, styling designer pieces with a DIY twist. For 1994’s Twelve Deadly Cyns album, she paired an electric blue Dolce & Gabbana shrug with a bowler hat that she spray-painted and decorated with feathers to match. “I wanted it to look like art,” she said, pausing by the ensemble as she wraps up the tour. “I remember that because it was another invention.

“That’s what makes it exciting,” she says. “That a young person would look and go, ‘I could do that.’”

• Cyndi Lauper: Suitcase of Memories, Part I is a live auction at Bonhams New York on 22 October. Part II runs online until 23 October