In 1986  her second album, ‘True Colors’ released in the fall of  that year, while it was successful with  the title track reaching number one and the album peaked at number four and went platinum, its softer, adult contemporary sound lost Lauper some fans. Cyndi’s musical career continued to spiral downwards in 1988 and  she made an attempt to breakthrough into the film industry with the comedy ‘Vibes’ but it also bombed at the box office. She went on to release her third album in 1989, ‘Night to Remember’ but it met with weak reviews and although it spawned the Top Ten hit "I Drove All Night," it suffered from disappointing sales, peaking at number 37.

1990 was the year that Cyndi broke her relationship with Wolff and went on to quickly marry actor David Thornton. Along with Debbie Harry, Cyndi Lauper became the face of the punk scene both in the US and the UK and Europe and at first, her music was a bright, colorful new wave fusion of a number of styles, including new wave, post-punk, reggae, pop, and funk. Her music and her appearance helped popularize the image of punk and new wave for America, making it an acceptable part of the pop landscape. Lauper didn't follow through on the success of her debut album ‘She's So Unusual’, instead choosing to turn toward middle-of-the-road ballad style and mainstream pop. But for many who remember the 1980’s, her first album remains a benchmark of that period.