41. EPMD "Jane" (1988)
Album: Strictly Business
Label: Fresh Records/Sleeping Bag Records Priority/EMI Records
The final song on EPMD's landmark 1988 debut Strictly Business is "Jane," a quick rap about a girl who pissed Erick Sermon off a few years earlier. Erick meets a girl named Jane who wants to hook up, but she'll only go out with him if he brings a friend for her friend. Erick drags Parrish out on a double date. Finally alone with Jane at the end of the night, Erick shows her what he thinks is the night of her life, but he awakes to a note that suggests the sex was wack. It doesn't really seem like the kind of story you'd want to make public, but EPMD had a thing for weirdly self-deprecating story songs typified by subsequent songs like "Who's Booty" and the series of sequels that "Jane" inspired.