Major Hit: "Bust a Move" (1989)

Other Hit: "Principal's Office" (1989)

It was all so simple then. Young MC garnered his record contract by rapping over the phone to Michael Ross and Matt Dike, owners of the famed LA-based record label Delicious Vinyl. The signing proved to be a smart move, as the rapper went on to record "Bust A Move," which won a Grammy for Best Rap Performance and pushed his debut LP Stone Cold Rhymin' to platinum status. He also collaborated with Tone-Loc on the writing of hits like "Funky Cold Medina" and "Wild Thing." Still, few remember Young MC's follow-up hit "Principal's Office." But we do—and now you do too.