96. Shyheim the Rugged Child "On and On" (1994)
Album: A/K/A The Rugged Child
This minor hit from Shyheim the Rugged Child, recorded when he was 16 years old, might sound lighthearted, but lyrically it deals with teenage prostitution and hard-headed underage hardrocks who get caught up in a cycle of violence. Although some of the appeal of the song might have stemmed from the undeniable appeal of a mini-Wu offspring, Shy is actually no joke on the microphone, and RNS' production is on point.