11. Lauryn Hill "Doo Wop (That Thing)" (1998)
Album: The Miseducation of Lauryn Hill
At the end of this song, Lauryn asks: "How you gon' win, when you ain't right within?" According to the Grammys that year, Lauryn herself was right within, winning five with her debut, The Miseducation of Lauryn Hill.
Her only No. 1 single, "Doo Wop," dedicated a first verse to women and a second to men, encouraging listeners to avoid the romantic pitfalls that she had seen or experienced firsthand. This was testament to the idea that rap could be used to uplift, unite, and empower women in a way that wasn't cloying.
Lauryn was able to walk the thin line that is a cautionary tale without too much self-righteousness, simply by inserting her own humanity, saying: "Don't think I haven't been through the same predicament." She has seen "that thing" in her own world and she just doesn't want you to be miseducated about it. —Alexander Gleckman