Debbie Gibson - Foolish Beat

Release date: 1988

This was Gibson's first American #1 single and it gave the 17-year-old the honor of becoming the youngest artist ever to write, perform, and produce a #1 single. The song captures the fantastical feelings of a teenage girl as she deals with heartbreak for the first time and wonders if she can ever love again.

Looking back at the song in a 2013 interview with Billboard magazine, Debbie Gibson said: "I find that people have kept (it) with them. I think it's because the lyrics are simple, but you can fill in the blanks with your adult experience." 

Album: Out of the Blue