42. 2Pac f/ Dave Hollister "Brenda's Got a Baby" (1991)
Producer: The Underground Railroad Album: 2pacalypse Now Label: Amaru/TNT/Interscope
This song became as famous for its music video as it was for its tale of a black girl lost. Over syrupy sweet '80s style R&B, Pac bears emotional witness to a common tragedy. Pac's narrative about the stress and fear that comes with having a child in the ghetto gave him an opportunity to speak to women, who were starting to pay more attention to him after his star turn in the film Juice. The success of this single taught him a critical lesson that would lead to a string of chart-toppers: Make music for female fans. They actually purchase music.