3. 2Pac "Brenda's Got A Baby" (1991)
Album: 2Pacalypse Now
Producer: Deion "Big D" Evans, The Underground Railroad
Between "Dopefiend Diner" and "So Many Tears," part of 2Pac's legend is his ability to tackle complex and difficult subject matter. The darkest moment in his catalog may very well be the narrative behind his first single. Inspired by a true story in the newspaper, 2Pac weaves a fictional plot about teen pregnancy and child abandonment that seared itself into the conscious of pop culture log before Teen Mom was on air.