47. A Tribe Called Quest, "Bonita Applebum" (1990)
My former Universal Records product manager, Grace Harry, hates when I introduce her (actually, I wait until her, well, applebum is turned the other way) in a whispered tone as "the real life Bonita Applebum that Q-Tip wrote about when they were dating in high school." There is no shame in that game, Grace! This is the song that truly birthed the idea of neo-soul. It was the coolest love song hip-hop has ever offered us. And that is miles better than being effective.