David Foster Wallace knew about Wittgenstein, Frege — and Ice T. Just republished by Little, Brown, Signifying RappersWallace's 1989 slim, smart volume written with his Amherst College classmate and novelist Mark Costello, is a reminder of both just how infinitely curious Wallace was and how relevant rap has always been to American popular culture.

Wallace was, arguably, the broadest literary mind of Generation X: he could write a novel about tennis and marijuana (Infinite Jest) and, also, muse on the ethics of boiling crustaceans while they are still alive (in the titular essay of Consider the Lobster). Back in 1989, though, he was just a 26-year-old Harvard graduate student (one who had recently attempted suicide; he would tragically succeed in taking his own life in 2008) living on Houghton St.

Many people have roommates; few have roommates who are on the cusp of literary greatness. Wallace had lived with Costello at Amherst and now asked the Boston native to move in with him. In his new introduction to this volume, Costello — who has written a novel of his own, Big If — is alone worth reading. He writes of living with Wallace in Boston:

Dave was more of a bar man than a club man, but … I could often talk him into a music crawl through the town. In 1989, humanity lacked the great and hungry search tools of today, Google, Yahoo, YouTube, Bing. But on mild Friday nights in dense-packed urban areas, we did possess another life-enlarging search engine. It was called walking.

This was precisely the cultural moment when rap was becoming mainstream, spurred along by Tone Lōc and Bobby Brown, the latter a native of the black Roxbury section of Boston. A friend of Costello’s – “a lefty lawyer for the tugboat workers’ union – arrived to stay at the Houghton St. apartment, brining tapes (this was, remember, when people still listened to tapes) of Slick Rick, N.W.A. and Public Enemy. Rap was thus in the air. Shortly thereafter, Wallace went to New York to meet with an editor, and the idea for Signifying Rappers was born.

Michael Pietsch, the CEO of Hachette Book Group (the parent company of Little, Brown) and a longtime editor of Wallace, told The Atlantic Wire, "Every book David published should be in print and available for his readers. Not only is Signifying Rappers his only collaboration, it is an early example of his distinct voice and shares the characteristics of all of his future non-fiction: a line-by-line melding of superb writing, cultural insight, personal observation, and analysis."

A book about rap written a quarter century ago by two very white guys has tremendous potential to be embarrassing. I am happy to report that Signifying Rappers did not make me cringe a single time, though I did have to look up both cultural references (Schooly D) and words from DFW’s famously capacious lexicon (epiclesis; seriously, Dave?). It is also probably the only book about popular music to seriously discuss the origins of synecdochal imagery.

At heart, this book has heart. Its message is simple and humane. “Rap is poetry,” Costello writes in the introduction — a poetry of protest, that is, speaking to what Wallace calls later in the book (the two write in alternating chapters) “the carcinomoid Other…inside Us” that frightens “Concerned Citizens” who do not want to hear about the macabre imagery of what Wallace and Costello call “Hard Rap.”

Because, remember, this is long before Jay Z was cavorting around with the leader of the free world and Ice Cube was making crappy family movies. The Ice Cube of N.W.A. (and make sure to google the meaning of that acronym) was singing lines like these, from “Fuck Tha Police,” released in 1989:

Ice Cube will swarm

On any mothafucka in a blue uniform

A young n---- on the warpath

And when I finish

It’s going to be a bloodbath

Of cops, dying in L.A.

Signifying Rappers tries to understand the attitude behind the confrontational rap of the late 1980’s without either condemning or fetishizing the genre. Wallace, in one of his sections – and they are, with no disrespect to Costello, more insightful than those of his partner – argues that “the unsubtle does not necessarily mean the simple or crude.”

Rap, he says, is black music for black people, presenting to its listeners a “a kind of dystopian present from which no imaginative future can emerge.” If this sounds a little earnest, or even naïve, remember that Wallace is writing about the genuinely angry verses of Public Enemy, hoarse with pleas from the ravaged Reagan-era ghetto, not the overproduced beats of Nelly and 50 Cent, who are playing solely to the market, their music largely absent of social value.

At the same time, Wallace applies the same kind of cultural analysis to rap that he would bring, memorably, to the cruise industry and Midwestern state fairs in the essay collection A Supposedly Fun Thing I’ll Never Do Again, published eight years after Signifying Rappers. He notes, for example, that rap borrows a tone of urgency from commercials for American Express and Oxy-5 acne cream, writing that “Rappers have merely wised up to the fact that crisis is the best salesman.”

Crisis would envelop rap in the ensuing decade. The same year as Signifying Rappers was published, 2 Live Crew’s As Nasty As They Wanna Be became the most filthy object ever foisted upon Western Civilization. Five years later, California congresswoman Maxine Waters would come to the defense of rap, calling it “a new art form to describe [our children’s] pains,” even as conservatives demonized the musical form as a great ill visited upon the inner city by its own denizens. As Wallace notes, “the Great White Male is rap’s Grand Inquisitor.” That was never more true than in the 1990s, as rap was steadily infiltrating the suburbs.

So maybe what’s most striking about Signifying Rappers is its sensitivity. Too many think of Wallace’s as the bard of cool irony, a dealer in pop-culture arcana. In fact, this book is more than the “deeply dorked-out artifact of 1989” Costello calls it in his preface, but an example of how to write about a culture that is not your own.

Speaking of which: In a famous 1997 skewering of John Updike in The New York Observer, Wallace lambasted a group he called the Great Male Narcissists for their fundamentally incurious outlook. That tradition, lamentably, continues, with the likes of Wallace peer Jonathan Franzen unable to imagine a convincing character who is not a hyper-intellectual, over-sexed Midwesterner: that is, himself. Costello and Wallace, driving around the bleak precincts of North Dorchester and Roxbury, saw a world that was not their own. And were curious about it, about what it said of the nation at large. That’s always a good place to start.

Photo of the South Bronx in 1977 by Associated Press.