Gracie Abrams Meets Cyndi Lauper: Two Generations of Pop Connect Over Songwriting, Shyness, and the Art of Reinvention

In a quiet studio in north Brooklyn, a rare and radiant exchange unfolds: Cyndi Lauper, the neon-haired powerhouse who defined the 1980s, and Gracie Abrams, the introspective Gen Z singer-songwriter who gives voice to emotional fragility, are sitting side by side — laughing, listening, and discovering that they share far more than a love of melody.

They’re surrounded by vintage records and warm light, heads bobbing to Rickie Lee Jones’ “The Last Chance Texaco.” It’s Lauper’s suggestion — a song Abrams, 26, admits she’d never heard until this moment. “I can’t believe you’re the person who showed it to me,” Abrams says, eyes wide. “If I ever heard that song out in the world, I’d want to leave wherever I was and go write. It just makes you want to beat everything you’ve ever done.”

Lauper laughs. Her Queens accent still carries the toughness and charm that made her an icon. “That’s what music’s supposed to do,” she says.

For both women, this meeting feels like fate. Abrams grew up with Lauper’s synth-soaked anthems — her mother’s favorite — filling their home. “There was such power in the air when your music was in the room,” Abrams says. “You’ve had the career you’ve had because you’re the one making all the decisions.”

Lauper shrugs with a grin. “I had to fight. I’m scrappy.”

The Soundtrack of Two Eras

Lauper, now 71, has just wrapped her 69-date farewell tour, announced a Las Vegas residency for next spring, and is set to be inducted into the Rock & Roll Hall of Fame this fall. Abrams, meanwhile, is at the start of her own legacy — fresh off her four-year run of shows, including her stint as an opener for Taylor Swift’s Eras Tour and multiple sold-out nights at Madison Square Garden.

Despite their decades apart, both artists have faced the same demons: shyness, creative block, and the unrelenting pressure to evolve.

“When I listened to ‘I Know It Won’t Work,’ I started crying,” Lauper admits. Abrams looks genuinely shocked. “Don’t say that to me! I can’t believe you listened to my music.”

“I listened to all of it,” Lauper says matter-of-factly.

The admiration flows both ways. Abrams, still in awe, says, “I adored your music before I even understood what you meant. The older I get, the more I understand its significance — as a woman, as an artist.”

The Shared Language of Songwriting

Lauper and Abrams soon dive into what they know best: the creative process. Both describe songwriting as an almost spiritual experience — equal parts discipline and divine accident.

“Sometimes you write something and think, ‘Wow, genius!’ Then the next day you go, ‘What the heck was that?’” Lauper jokes. “Ain’t that what we do?”

Abrams nods. “There’s this weird trance when it works. You almost black out for a second, and then suddenly — the song’s there. That’s the drug.”

Lauper laughs knowingly. “Kind of addictive, yeah.”

But even legends face doubt. “I always think, ‘I suck,’” Lauper says, chuckling. “Then I tell myself, ‘Get the bad stuff out, move on, find the good one.’ It’s three or four chords — how bad can it be?”

Abrams relates instantly. “I go through that cycle every time,” she admits. “I feel like I’ll never write again — and then something hits.”

From Catholic School Rebel to Hall of Famer

As the conversation deepens, Lauper recalls her mischievous school days with characteristic candor. “I got kicked out of Catholic school — twice. Once for talking back.”

Abrams bursts out laughing. “They just didn’t want to hear everything you were right about.”

The two share a moment of understanding — both shaped by the tension between defiance and vulnerability. Lauper, who built a career on bold individuality, sees that same spark in Abrams’ introspection. “You’re doing what I did — you’re saying what you mean,” Lauper tells her.

Finding Power on Stage

Abrams admits that performing didn’t come naturally. “I never played in front of anyone before the pandemic,” she says. “The night before my first show, I was up all night throwing up from nerves.”

Her first performance — a small gig at the Observatory in Orange County — changed everything. “It was tiny, maybe 100 people,” she recalls. “I wore a gray dress and blue Converse. I didn’t even brush my hair.”

“Was that like a big ‘Screw you’?” Lauper teases.

“Honestly, I was just terrified,” Abrams laughs. “But then I realized performing is actually fun. People were having a good time — that was enough.”

Lauper nods knowingly. “That’s the community. That’s where we win as people.”

The Creative Rituals

For Lauper, songwriting often begins with cleaning the house. “When I’m in motion, all this stuff comes to me,” she says. “I don’t know why. Maybe it’s the rhythm of it. My mom used to say, ‘Clean up the room,’ and I’d end up sitting with my guitar instead.”

She’s currently writing a new Broadway musical adaptation of Working Girl, following her Tony-winning success with Kinky Boots. “It’s been 10 years in the making,” she says. “It’s worth it — it’s about where we are now, how the world’s changed for women.”

Abrams is in a different kind of transition — her last tour just ended, and her next album hasn’t yet taken shape. “I don’t know what I want to say yet,” she admits. Lauper smiles and says simply, “Take a breath.”

Passing the Torch

As their conversation winds down, Abrams becomes reflective. “The older I get, the more grateful I am that I was raised in a house where your music was playing,” she tells Lauper. “Now I can apply those songs to my own life.”

Lauper grins. “Well, I’m surprised you weren’t dancing around to them!”

“I was too shy,” Abrams confesses.

“Doesn’t matter,” Lauper says. “You’ve got your whole life now. You’re going to make it. You’re going to write the book.”

It’s a moment of quiet mentorship — one legend handing down not advice, but belief.

Two generations of artists, separated by four decades yet united by the same calling, sit surrounded by music and laughter. For a few hours in Brooklyn, time bends: the woman who told the world that girls just want to have fun meets the woman teaching a new generation how to feel — and both realize they’re still learning how to listen.

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