Jenifa Taught Me (Derwin's Revenge)

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De La Soul is best known as the clown princes of hip-hop, yet the group spent a lot of time rapping about sex, though in their typically lighthearted style. One of the most notable examples is 3 Feet High and Rising's second single (the flip was the popular "Potholes in My Lawn"), which details a clumsy early hookup. According to De La Soul rapper Dave, "Derwin is a friend of ours who we used to crack on because he never got no girls. He loved the song, of course. It put him on the map."