Tiffany
She was the Mall Queen of teen America in the late 1980s, and the red-haired pop starlet scored huge hits as the decade came to a close. However, as she crossed over into adulthood, Tiffany found it majorly difficult to sustain any kind of musical career. She released a sexier, more R&B-influenced album at the age of 21 that failed, and eventually wound up posing for Playboy.
Debbie Gibson
The other mall princess of the late 80s was also a squeaky-clean girl-next-door, and the future “Deborah” Gibson was also noteworthy in that she wrote her own songs. But after she entered her early 20s, she attempted to make a musical comeback with a racy 1994 video that featured the 22-year old as a burlesque performer. The album peaked at only #109 on the Billboard charts.
