44. Debbie Gibson
Band Or Solo Artist?: Solo
Genre: Pop, R&B, Rock
Greatest Hit: "Foolish Beat" (1988)
In 1988, Gibson became the youngest artist to produce, write and perform a number one single, "Foolish Beat," on the Billboard Hot 100, a record that still remains unbroken. Like Britney Spears, Gibson started as a teen but grew into a bonafide '80s hottie (who still looks good today). Consider her the pop princess of her generation.