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Cyndi Lauper on how her iconic hairstyles reflected her life's defining moments

2:05
American Music Awards
Cyndi Lauper breaks down her iconic hairstyles from the '80s to now
Ron Galella Collection via Getty
ByShannon Caturano
July 21, 2025, 10:07 PM

Cyndi Lauper's bold, ever-changing hairstyles have always been more than just a fashion statement -- they were acts of rebellion.

In an interview with "Good Morning America" Digital, Lauper revealed that her half-shaved head in the "Time After Time" music video symbolized defiance at a time when women were "haunted by the image of their mother in a life of drudgery."

"Cutting my hair in that way would also be a rebellious act, one culture fighting to move away from a more oppressive culture for women," she said.

Lauper said she surprised Dave Wolff -- her longtime boyfriend in the '80s and former manager -- with her haircut, revealing her new red style for the first time while the cameras were rolling in the video because she wanted his reaction to be "natural."

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"The hair symbolized a counterculture and rebellion, and that was significantly important to me," she said. "If you're going to color your hair, you might as well ... color it a color."

Lauper also reflected on a deeply personal moment in the video: The tears she shed onscreen were real.

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She said it was the moment she realized she had made it as a rock star, recalling how she had once faced homelessness and was voted "most likely to die" by her peers in school.

"I was either going to expire or be this artist, and I wound up being this artist," she recalled. "That's why I was crying, because I couldn't believe life had given me that gift."

Nearly 40 years later, the video has amassed more than 500 million views on YouTube, proof of its lasting cultural impact.

"It became a classic because I think I spoke to people," Lauper said.

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Lauper added that the video's message still resonates, because women today can relate to the feeling of not wanting to fit in.

"From the clothing to the hair to the makeup, it symbolized one culture fighting to move away from a more oppressive culture for women," she said.

Lauper told "GMA" her hair has been an outlet for her creativity over the years and a way to encourage women.

Below, she described the inspiration behind some of her most memorable styles.

Photo shoot, 1983

Cyndi Lauper portrait session in London June 15, 1983.
Terry Lott/Sony Music Archive via Getty Images

"Red hair, I just liked the way it felt," she said. "And it wasn't just regular red, it was a crazy color. I think at that point I was using fire-engine red, and sometimes it was brighter than others."

American Music Awards, 1985

Cyndi Lauper attends the American Music Awards, Jan. 28, 1985.
Ron Galella Collection via Getty

"For the 'Money Changes Everything' music video, that was the color. Everything was black and white except for my hair, and that was painted," she said.

Performing in Chicago, 1999

Cyndi Lauper performs in Chicago, Sept. 2, 1999.
Paul Natkin/Getty Images

"A friend of mine had done her hair in dreads, and I said, 'How do you do that?' Because it looked like once you could do it, you didn't have to mess with it," Lauper recalled.

She continued, "I had done my hair blue, which I liked at the time, and it was after I had my kid, and I just did my own dreads, and I was doing my own hair on tour … it looked good."

Melbourne concert, 2023

Cyndi Lauper performs during a concert supporting Rod Stewart, March 14, 2023 in Melbourne, Australia.
Sam Tabone/WireImage via Getty Images

"I like mohawks, and, yeah, purple is good," Lauper said. "A lot of times, you know, if it's spring, I get it. Inspired by the flowers, you know, and tulips."

Lauper has seen tremendous success over her decadeslong career, earning two Grammy Awards, a Primetime Emmy Award, a Tony Award for co-writing "Kinky Boots," four Billboard Music Awards, two American Music Awards, and a star on the Hollywood Walk of Fame.

Her debut album from 1983, "She's So Unusual," made history as the first by a woman to score four top-five hit singles, including the iconic "Girls Just Want to Have Fun" and "Time After Time."

She is set to be inducted into the Rock & Roll Hall of Fame in November.

Lauper is currently on the last leg of her yearlong Girls Just Wanna Have Fun Farewell Tour, with 21 shows left in North America this summer.

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