This week, Mark Costello and David Foster Wallace’s Signifying Rappers: Rap and Race in the Urban Present is back in print from Back Bay Books. The 1990 intellectual frolic has mostly been the missing piece in Wallace’s oeuvre, often dismissed as juvenilia while he was alive, then being consigned to expensive, out-of-print territory, even after his death, when all things DFW piqued readers’ interest. It’s a curious, often precocious book from an era when thinking hard about hip-hop and seeing how far down the grad-school rabbit hole it could take you was a relatively new phenomenon.
In the case of Signifying Rappers, Costello and Wallace compared Bob Dylan and Flavor Flav, exhibited an unhealthy obsession with the high-low bridging of Schoolly D’s 1988 track “Signifying Rapper,” and dropped far too many self-deprecating “we’re clueless white boys” asides. But it’s also got some fairly quintessential proto-DFW moments. For a sense of what this strange little book is all about, here are ten of the most memorable quotes from Signifying Rappers.