Song: "Exhibit C" (2009)
Album: Exhibit C EP

One of the most quietly dark lines on this list, that, like so many others, puts you right in the author's shoes with a few brief words. But while many a rapper will rap from coming from nothing, being homeless and destitute is an altogether different thing, one you're not going to hear referenced too often. Herein, Jay is sleeping in both a literal and figurative sense: he's asleep but he also lacks "knowledge of self." The song, which explores his spiritual awakening and how he turned his life around, all begins here, with the most square-one setup possible: With nothing to lose, on Meserole Ave.