Cyndi Lauper Then & Now: Pictures of the Pop Singer Over the Years

The ‘80s would not have been the same without Cyndi Lauper. The singer is a living music legend so take a look at Cyndi from her younger years to today.

Born Cynthia Ann Stephanie Lauper, the icon known as Cyndi Lauper burst onto the scene in the early 1980s thanks to her album She’s So Unusual. With that LP, she broke through the glass ceiling — it became the first debut album by a female artist to achieve four top-five hits on the Billboard Hot 100. First working with the band Blue Angel, Cyndi then established herself as a solo artist with her version of “Girls Just Want to Have Fun.” Her music and fashion became synonymous with the 1980s, blending early punk, new wave, and pop into a unique sound and signature style.

Cyndi won the first-ever MTV Video Music Awards’ Best Female Video prize in 1984 for “Girls Just Want to Have Fun,” and has been recognized as one of the greatest music videos of the era. She has also won countless awards at the Grammys, Emmys, Tonys, and VMAs.

Beyond her music, Cyndi has built a respected acting career, appearing in hit TV shows like Mad About You, Bones, and That’s So Raven, as well as films such as Vibes, Life With Mikey, and Henry & Me. She even made a cameo in The Goonies, contributing the beloved theme song “The Goonies ‘R’ Good Enough.”

Cyndi is also a lifelong LGBTQ+ advocate, co-founding the True Colors Fund to combat youth homelessness and champion equality. Now celebrating her Rock Hall induction, decades of hits, and the announcement of her farewell tour, Cyndi Lauper continues to prove that true icons never fade — they just keep inspiring new generations to be unapologetically themselves.

Want to learn more? Take a look at Cyndi and marvel at this icon in our gallery!

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