Signifying Rappers: Rap and Race in the Urban Present, an experimental study of rap – labeled, variously, within the book as a “sampler,” a “literary essay,” and a collection of “theses about why serious rap is important” – published in 1990, coauthored by Mark Costello and David Foster Wallace, has received a surprisingly small amount of academic and cultural attention.Footnote ¹ Despite the fact that the public appetite for unpublished or little-known Wallace material has in recent years been so insatiable, Signifying Rappers is only now being reissued and repackaged, with a new introduction from Costello, nearly five years after Wallace's tragic and untimely death. Other posthumous publications and reissues include Wallace's undergraduate philosophy dissertation, Fate, Time, and Language: An Essay on Free Will (2011); a previously uncollected edition of essays and occasional writings entitled Both Flesh and Not (2012); a transcript of Wallace's 2005 Kenyon College commencement address, given the title This Is Water (2009) and printed in a bizarre, one-sentence-per-page, Little Book of Calm-like format; and several collections of interviews, including Conversations with David Foster Wallace (2012) and David Foster Wallace: The Last Interview and Other Conversations (2012).Footnote ² Along with several academic studies, the list of posthumous publications also includes D. T. Max's meticulously researched biography Every Love Story Is a Ghost Story: A Life of David Foster Wallace (2012) as well as, most significantly, 2011′s The Pale King, edited and organized by Wallace's Little, Brown & Co. editor, Michael Pietsch. The fact that obscure and esoteric texts, such as the aforementioned Fate, Time, and Language, a forbiddingly dense academic paper with limited general-audience appeal, have found mass-market release makes the omission of Signifying Rappers even more conspicuous. Highly conscious of the book's curiously overlooked status, this article offers a detailed re-examination of Wallace's foray into music criticism, arguing that the book offers a revealing glimpse into his development as both a fiction writer and an essayist. The article begins by tracing many of Wallace's subsequent thematic concerns and literary techniques back to this early text, as well as positioning the work within the larger trajectory of his career. Ultimately, this retrospective reading shows that far from being a mere curiosity piece in Wallace's corpus, radically disconnected from anything he published either before or after, a close interrogation of Signifying Rappers enriches our understanding of Wallace's work, revealing an oblique vision of Wallace striving to articulate a personal artistic agenda in response to the postmodern literary tradition. The essay proceeds to address Wallace and Costello's uncanny presaging of many of the preoccupations of institutional hip-hop and whiteness studies, offering an extended interpretation of the text in light of these disciplines. This analysis also explores representations of race within Wallace's work more generally, as well as addressing the underlying reasons behind the obscure status of Signifying Rappers within these two related fields. The overriding thesis of the article is that, although in many ways a problematic text, there are numerous significant attributes that render Signifying Rappers worthy of wider scholarly and public engagement.

There are currently no sustained literary analyses of Signifying Rappers, and even monograph-length enquiries into Wallace's writing gloss over the book – or else entirely omit it from discussion. Tellingly, The Legacy of David Foster Wallace (2012) includes Signifying Rappers in a list of Wallace's publications but contains no other references to the text, clearly indicating its nonexistent scholarly legacy. One possible explanation for the absence of scholarly interest in Signifying Rappers is the fact that literary collaborations are notoriously difficult to account for. The fact that the book was cowritten with Wallace's friend and fellow Harvard student Mark Costello, thus further muddying the hermeneutic waters of intention and purpose, surely goes a long way towards accounting for this scholarly reticence.Footnote ³ Part of the explanation behind such reticence is surely an attachment (whether conscious or otherwise) to the persistent myth of the Romantic, impassioned author, whose writing gushes forth from the depths of his soul, unsullied by any form of mediation or compromise, a phenomenon labeled by Stone and Thompson, in their 2006 edited collection Literary Couplings: Writing Couples, Collaborations, and the Construction of Authorship, as the prevailing “paradigm of the unitary author.”Footnote ⁴ Or, as Wallace himself described it, as the Wordsworthian notion of “the text as the creative instantiation of the writer's very self.”Footnote ⁵ A great deal of popular writing on Wallace has sought to position Wallace in just this way – as a sui generis, anomalous figure, who emerged without artistic precedent – as has, occasionally, some academic criticism. Although early critics writing on Wallace perceived Infinite Jest's engagement with an American postmodern tradition, it is striking that it took until 2001, with the publication of Timothy Jacobs's “American Touchstone: The Idea of Order in Gerard Manley Hopkins and David Foster Wallace,” before detailed comparative analysis was carried out on the novel, despite Wallace's writing being replete with intertextual references and allusions, along with the fact that many of his nonfictional texts and interviews indicate an engagement with a diverse range of prior literary figures. Dave Eggers contributed to this discourse of artistic exceptionalism in the gushing preface to the tenth anniversary edition of Infinite Jest, claiming that the novel

While there is a shred of truth in Eggers's effusions, the claim that Infinite Jest is wholly without precedent is a misleading one. As scholars have consistently demonstrated, Wallace's novel owes significant artistic debts to a diverse range of fictional and theoretical texts, among them Don DeLillo's End Zone, Dostoevsky's The Brothers Karamazov, the poetry of Gerard Manley Hopkins, Hamlet, and Lacanian theory.Footnote ⁷ Thus, even before acknowledging the explicitly collaborative influences upon his work, the notion of Wallace as an unprecedentedly original, sui generis figure is clearly untenable.

Furthermore, in spite of this institutional reluctance to tease out the murky strands within jointly authored texts, Signifying Rappers presents a relatively straightforward intellectual partnership. Although Wallace and Costello no doubt revised and offered suggestions for each other's work, each section of the text is clearly labeled either “M.” or “D.,” clearly differentiating between the two writers' contributions. Thus the text is less collaborative than would initially appear, and reasonably straightforward demarcations can be made about Wallace's share of the work, diminishing a large part of the critical hesitancy surrounding the collaboration. Given Wallace's cultural significance, it is difficult not to relegate Costello's role to the “Sancho Panza” or “Alice-Toklas-esque” (25) DJ position Wallace refers to in his differentiation between the “MC/rapper and his record-scratching, sound-mixing Sancho Panza, the DJ” (24).Footnote ⁸ Although Costello is a successful author in his own right, having published the acclaimed novels The Bag Men (1997) and Big If (2003), this article limits itself to a discussion of the book in relation to Wallace's career. Hence all quotations are from Wallace's sections of Signifying Rappers, except where noted.

A further impediment to the book's academic reception has been the fact that, aside from a handful of brief mentions in the 1993 McCaffery interview, Wallace rarely, if ever, mentioned Signifying Rappers in other contexts. It is highly odd, for instance, that David Lipsky's 1996 interview, conducted on behalf of Rolling Stone and later republished as Although of Course You End up Becoming Yourself (2010), asks only one, fairly innocuous, question about Signifying Rappers; in response to the query, Wallace stated that the book allowed him to feel productive during a period in which he was both “terrified to write fiction” and “desperate to feel like a writer.” Working in a collaborative manner gave Wallace a concrete literary project while he waited until he was able to return to fiction: he told Lipsky that whenever he attempted fiction, “it was just an incoherent mess.”Footnote ⁹ In addition to rarely mentioning the book in interview contexts, he never again returned in his writing either to music criticism in general or to hip-hop in particular, despite claiming, in other contexts, both that music is an art form “that is jacked pretty much directly into people's emotions” and that “God has particular languages, and one of them is music.”Footnote ¹⁰ But even this silence can be misleading, for although Wallace repeatedly distanced himself from his first two publications of fiction – 1987's The Broom of the System and, to a lesser extent, 1989's The Girl with Curious Hair – he never publicly disavowed his expedition into music writing. Presumably, critics have used Wallace's silence as reason for neglecting the work, as they may well also use D. T. Max's recent dismissal in Every Love Story Is a Ghost Story. Max's biography rapidly glosses over Signifying Rappers, arguing that Wallace's interest in hip-hop was, ultimately, merely “theoretical, verbal, abstract,” that it never “touched him” in the way other musical forms did: “His interest had the quality of a very smart kid slumming it.”Footnote ¹¹ It may be true that Wallace's musical tastes encompassed other genres, but it seems odd to suggest that Signifying Rappers, a rigorously detailed and researched study, could be produced by a writer wholly detached from the emotional aspects of the music. Although Wallace's motives for writing the collaborative text were somewhat pragmatic, at the time he was clearly enamored with the genre.Footnote ¹² Indeed, the effusive and borderline evangelical tone used throughout much of the book calls into question Max's assessment. In light of the critical silence surrounding the text, Max's appraisal seems to provide yet another reason for ignoring or dispensing with the text. Perhaps understandably, Max's overriding interest, in the sections of the biography that discuss the book, is in contextualizing the work in relation to Wallace's life, though his dismissal of Signifying Rappers, and its potential to further ghettoize the text within Wallace studies, is one of the key claims the article takes issue with.

Despite the fact that almost twenty-four years have passed since the first publication of Signifying Rappers – Wallace points out early on that “[i]f you're reading this in print it's already dated” (71) – our contention is that even aside from being an insightful glimpse into Wallace's career trajectory, the monograph has numerous virtues in and of itself, virtues that save it from being a mere period piece, of only historical interest. To begin with, despite early reviewers' accusations of its being overly cerebral, the book has an infectiously exuberant quality; there is a joyousness in the writing that is expressed through playful experimentation with language.Footnote ¹³ One example of this kind of experimentation is in Wallace's use of compound conjunctions to open sentences (“And but you can feel” (43), “But so the point is …” (47), and “Well, but except …” (94)), a technique that would become a hallmark of his later writing, and gives the prose an oral, spoken quality. Passages that open with such phrases have a frenetic, breathless tone, as if the author cannot spare the time to form conventional linkages between sections and is racing to get the next idea down on the page before it escapes him. The frequent use of ellipses throughout the text also contributes to this feeling, creating an impression that the text is more spontaneous and unedited than it surely is. As a rhetorical gesture, this is a canny deployment, since it makes the pronouncements within the book (many of which offer provocative reflections on race and class, and are thus culturally sensitive) seem slightly more preliminary, as if the author is rehearsing a particular line of reasoning or argumentation, instead of being entirely wedded to the opinions expressed. In this way, Wallace's heightened self-consciousness, as a “white yuppie” (20) writing on “music of, and for, blacks” (21), is mirrored on an orthographic level. Frequently, these ellipses either indicate a new, though tangentially connected, idea or else interrupt or fracture a line of reasoning, as in the following section, in which Wallace claims that the self-consciousness

Here the interruption works as a kind of representational “Aha!” moment, in which Wallace dramatizes the way in which a particular line of reasoning can lead to an unexpected, epiphanic conclusion. This mimetic representation of thought is one of Wallace's most significant contributions to literary nonfiction, creating a kind of overheard, performed interiority. Intriguingly, Wallace also uses such pauses between paragraphs, in a manner that suggests a stronger-than-usual connection between paragraphed ideas and also contributes to the performative quality of the text. Continuing from the passage quoted above, Wallace links together two separate paragraphs via double ellipses:

This representation of thought-in-motion is both a means through which Costello and Wallace can explore sensitive political and racial content, and a key factor in explaining the book's literary virtue.

The linguistic experimentation throughout Signifying Rappers, much of which has come to define Wallace's distinctive prose style, also includes capitalized nouns, used to great effect in flagging key media and political abstractions – such as “the rhetorical relation of Part to Whole” (38), “Great White Male” (24), and “Yuppie America” (63) – that have enormous potency in cultural discourse. At times such capitalizations are even portmanteaued into abstract noun clusters, denoting a string of commonly joined buzzwords, as in the aforementioned quotation, in which Wallace discusses the way rap artists present “DrugsViolenceGreedDespair as an artistic choice” (44). Foreshadowing the abbreviated language of electronic communication are Wallace's many truncations, among them “thru” (33), “w/o” (102) for without, “mothafucka” (98), “stats” (100), “'scope” (40) for telescope, “dissed” (96), “music biz.” (71), “Yr.” (126), “vocab” (100), “w/r/t” (84), the exclamatory “… WHA?” (45), “more $” (71), “rep.” (30) for representative, and “AKs” (27) for AK-47 assault rifles. Neologisms also abound: Wallace consistently uses such inventive constructions as “yuppiness” (20), “trochee'd rhymes” (20), “multiple-earring'd” (101), “kaboom” (70), “pre-Ph.D.'s” (27), “the media-We” (39), “defness” (123), “huge-afro'd funk” (70), “malschooled” (99), “untalent” (114), “probably appropriater yet” (84), and “avant-avant-gardists” (128). Some of these neologisms are more successful than others, though there are many comical and innovative wordplays, as in the line “… an attitude we all pretended was so-very-phisticated” (124) and the reference to “Public Enemy's be-clocked Flavor Flav” (101). And though the book's vocal reproductions are not strictly neologisms, Wallace also finds novel ways to represent spoken American English in both the repeated – and surely, in 1990, stylistically unusual – use of “like” as a vocalized pause, as in sentence fragments such as “Do those of you in like Chicago or NYC …” (69) and “since like around Homer” (99), as well as in the frequent use of colloqualisms, among them “so freaking long” (95), “godawful” (114), “dicklessness” (118), “tight-ass” (114), “well pardonnez-moi but …” (118), and the resigned “it'll be hard to fucking care” (121).Footnote ¹⁴ In the same vein, the text's insistence on using contractions – “it's” (69), “what's” (69), “you're” (71), etc. – also contributes to the text's aforementioned oral quality.Footnote ¹⁵

The book's oral, spoken quality cannot be emphasized enough. All the usage decisions outlined above render the book a kind of transcribed address: as though two intelligent, impassioned hip-hop fans, both brimming with opinions and theories about the genre, are sitting down with the reader to discuss the music they revere. In this way, the book fits neatly alongside Wallace's intention for his fiction, as being “like a late-night conversation with really good friends, when the bullshit stops and the masks come off.”Footnote ¹⁶ As previously mentioned, the authors' extreme self-awareness of writing on rap from an extramural perspective is to some extent lessened by the spontaneous, first-draft quality that such techniques create. It is surely no accident that the text contains so many colloquialisms, contractions, interjections, and ellipses: such techniques, along with the dialogic interplay of Costello and Wallace's alternating arguments, signal that Signifying Rappers is clearly meant to be received with the expectations of speech, rather than text. A later correspondence sheds light on this curious textual quality; writing to Harper's editor Joel Lovell on the inclusion of his PEN/Faulkner address on Kafka (entitled “Laughing with Kafka”) in a forthcoming issue of the magazine, Wallace stressed that he wanted all “[i]diosyncracies [sic] of ital, punctuation, and syntax” left unchanged, arguing, “A big reason for this is that I want to preserve an oralish, out-loud feel to the remarks so as to protect me from people's ire at stuff that isn't expanded on more.”Footnote ¹⁷ Clearly, a similar impulse is at work in Signifying Rappers: Wallace's extreme self-awareness of his outsider status and corresponding fear of public “ire” is at least partially obviated by the text's “out-loud feel.” Incidentally, there is something deeply counterintuitive about Wallace's frequent insistence on the spoken quality of his prose; for an overeducated “pre-Ph.D.” (27) student schooled on Derrida and de Man, Wallace would surely have been intimately familiar with the post-structuralist critique of phonocentrism. Indeed, there is a seeming disjuncture between Wallace's commitment to constructing prose with an “oralish, out-loud feel” and Derrida's critique of an unacknowledged Western “metaphysics of presence.”Footnote ¹⁸ In his 1991 review of H. L. Hix's Morte D'Author: An Autopsy, Wallace revealed a comprehensive knowledge of structural/post-structural theory, and appeared tacitly sympathetic to the post-structuralist position on phonocentrism, pointing out that

Wallace's summary points to one of the central tensions animating his own work, particularly in the years following his death: the contrast between an intimate sense of authorial presence and the alarming awareness of utter absence.

Signifying Rappers's dazzling level of linguistic experimentation seems primarily born out of a mimetic impulse, the desire to have the book's language respond to the wildly inventive genre under discussion. As SPIN magazine's Brandon Soderberg notes, the fact that, in the late 1980s, the rules governing hip-hop criticism were not yet codified “gives the book an unfettered freedom that couldn't exist at any other moment in hip-hop history.”Footnote ²⁰ Though Wallace's writing before this point was still stylistically unique, writing on rap gave Wallace license to use all kinds of linguistic invention, appropriating the wild energy and freneticism of hip-hop to create a deeply idiosyncratic writing style. Far from producing what one early reviewer uncharitably described as “choppy, awkward and confusing … literary prose,” Wallace's sections of the book display all the linguistic virtuosity that would later earn him widespread critical acclaim.Footnote ²¹ Indeed, one of the aspects that attracted magazine editors like Harper's Magazine's Colin Harrison to Wallace was the book's outlandishly experimental and comic prose style. As Marshall Boswell points out, it was “on the strength of Signifying Rappers” that “Harper's began sending [Wallace] out on unconventional journalistic assignments,” further testifying to the argument that Wallace's literary nonfiction prestige can be traced back this text.Footnote ²²

Importantly, Signifying Rappers also functions as an oblique primer on many of the themes and preoccupations of Wallace's subsequent career. His sections of the book implicitly install hip-hop as the creative epitome of postmodern art, arguing that its complex poetic innovations, representational verisimilitude, and disturbingly profound distillation and reflection of Reagan-era economic logic – all of which Wallace illuminates so memorably – justify its exemplar status. However, although Wallace's enthusiasm for the genre is so clearly evident, many passages also express misgivings about certain aspects of hip-hop, prophesying its logical endpoint and exposing its thematic lacunae in a manner that closely resembles Wallace's critique of postmodern fiction. In fact, throughout much of the book, it is possible to observe Wallace rehearsing many of the arguments that will later come to define his approach to fiction. Crucially, he even searches for a signifier to denote whatever will follow postmodernism, in his claim that “[s]erious rap's the first music to begin creative work on the new, (post-)postmodern face the threat of economic inequality to American ideals is wearing” (121). This tentative, parenthetical attempt at definition reveals Wallace attempting to foresee whatever lies beyond the coordinates of postmodernism, a recurring impulse in both his fiction and nonfiction.Footnote ²³

Furthermore, his key preoccupation – returned to at numerous points throughout the text – with the ways in which subversive black music has been coopted by white media and corporate record labels mirrors his later thesis (expressed most compellingly in 1993's “E Unibus Pluram”) on the countless ways in which advertisers and commercial artists have appropriated and thus eviscerated postmodern fictional techniques, while his recurring emphasis on rap's myriad “sources” (12) reveals Wallace working through the implications and meaning of artistic influence. In addition, his frequent attacks on contemporary US poetry's insularity (together with his uneasy feeling about hip-hop's audience: “what if cutting-edge rap really is a closed music?” (45, original emphasis)) relate in clear ways to the closed nature of much experimental literary fiction, which only a small coterie of initiates can appreciate or understand, while the cyclical, eternally self-replicating version of the American music thesis Wallace advances mimics the “crank-turn[ing]” theory of contemporary fiction he spoke of at length in his 1993 interview with Larry McCaffery.Footnote ²⁴ Perhaps most significantly, Wallace's concerns with hip-hop's overriding cynicism and lack of a positive program – the fact that it has “no vision of anything beyond present discontent” (127) – is a refracted version of his later critique of “postmodern lit” (1993, 58), in its tendency to endlessly ironize and debunk the culture without proposing any positive content in its place. Thus an attentive reading of Signifying Rappers allows us to observe the ways in which Wallace was rehearsing, in an indirect and veiled manner, the artistic agenda he would shortly set forth.

Perhaps just as curious as Signifying Rappers's lack of recognition from literary scholars is its minimal impact on the now-flourishing discipline of hip-hop studies. Despite prominent music critic Rachel Kaadzi Ghansah's recent appraisal of the book as “one of the finest essays ever written about rap music,” Signifying Rappers has, on the whole, been dismissed by the canon of rap criticism.Footnote ²⁵ This dismissal is particularly intriguing given that Signifying Rappers, published in 1990, actually precedes Tricia Rose's Black Noise: Rap Music and Black Culture in Contemporary America (1994), a monograph that is almost uniformly acknowledged within hip-hop studies as the seminal work in the field.Footnote ²⁶ Only a handful of scholars, however, even acknowledge the existence of Signifying Rappers: Wallace receives passing mention in William Eric Perkins's introduction to Droppin’ Science: Critical Essays on Rap Music and Hip-Hop Culture (1996), for his description of sampling techniques; in Russell Potter's Spectacular Vernaculars: Hip-Hop and the Politics of Postmodernism, which offers a decidedly dismissive reading of Wallace and Costello's approach to rap; in Robin D. G. Kelley's essay “Looking for the ‘Real’ Nigga: Social Scientists Construct the Ghetto”; and in Andrew Bartlett's “Airshafts, Loudspeakers, and the Hip-Hop Sample,” though these essays merely gesture to Signifying Rappers rather than engaging it in any significant way.Footnote ²⁷ It is also completely absent from later works concerned explicitly with whiteness and hip-hop, notably Bakari Kitwana's Why White Kids Love Hip Hop, Michael Jeffries's Thug Life, and Jason Tanz's Other People's Property (2007).Footnote ²⁸

That Signifying Rappers has not made more of an impact on studies of hip-hop and race is regrettable: the study articulates, at times problematically but always in a spirit of cross-cultural earnestness, a fascinating confrontation of race and critical engagement that both pre-dates critical whiteness theory and sheds light on an area of Wallace's intellectual curiosity that is seldom explored. Scholars have not yet written in detail about Wallace's often curious depictions of race and racial issues. Kathleen Fitzpatrick, in The Anxiety of Obsolescence, includes a brief discussion of Wallace approach to race in formulating the provocative thesis that “[c]anonical postmodernist fiction works to … retreat into the purity of universal white masculinity,” while Emily Russell's 2010 article “Some Assembly Required: The Embodied Politics of Infinite Jest” makes passing reference to the ways in which “the discourses of medicine, entertainment, religion, race, gender, and sexuality operate in a network to construct how we understand bodies,” but focuses on Infinite Jest's description of athletic bodies rather than its presentation of race.Footnote ²⁹ There is, however, something odd, and potentially revealing, about the fact that although he applied intellectual rigor and complex analysis to such obscure topics as sports autobiography, animal rights, talkback radio culture, pornography, and the films of David Lynch, Wallace never again wrote directly on racial issues. Despite living for many years in Bloomington, Illinois, a town largely populated with “educated republicans” and with fairly prominent racial segregation issues – in an interview, Wallace himself described the racism in Bloomington as “very quiet, very systematic” – it is intriguing to speculate on the reasons why Wallace shied away from this particular form of cultural analysis.Footnote ³⁰ Although highly self-conscious about what he labeled his own “resounding” whiteness, there are several highly curious racial comments and portrayals through his work: Wallace was sentimentally proud of Welsh/Scottish ancestry (in 1989 he sent a postcard to David Markson that featured the Wallace clan tartan, and once admitted to having wept patriotically at the end of Mel Gibson's Braveheart), concerned that he would be perceived “as anti-Semitic” because he did not approve of the narrative arc of Schindler's List, and in graduate school wrote “a long novella … about a wasp who passes himself off as Jewish.”Footnote ³¹ Finally, Jonathan Franzen's infamous 1996 essay “Perchance to Dream” includes a piece of correspondence from Wallace to Franzen that laments the ways in which mainstream culture has “alienated” white males, a sentiment that reflects the outsider compulsion of Signifying Rappers.Footnote ³² Wallace's letter argues that while “tribal writers can feel the loneliness and anger and identify themselves with their subculture,” the fact that “[w]hite males are the mainstream culture” means that they operate from a more difficult cultural position: “so why shouldn't we be angry, confused, lonely white males who write at and against the culture?” (51, Wallace's italics).

Indeed, a primary concern of Wallace's is the notion of positionality – that is to say, his whiteness – a consideration that looms large in the disciplinary foundations of what is now known as whiteness theory. He and Costello make frequent reference to their “outsider” status as white males attempting to interpret hip-hop, presumably keen to underscore their assertion – however problematic – that rap is “black music, of and for blacks” (21), and that “whatever musical or socio-political importances [sic] there are in rap/hip-hop are pretty obviously there to be drawn out by and for black people” (48). From the outset, their analysis is plainly preoccupied with issues of “entitlement” – the title of their opening chapter – anticipating the kinds of whiteness studies subsequently undertaken by white scholars in the mid- to late 1990s.Footnote ³³ In a statement that recalls Greil Marcus's thesis on cultural appropriation in Mystery Train (Wallace, in a 1991 LA Times review of Marcus's Dead Elvis, lauded Marcus as a “genius”), Wallace is careful to note that “everything the white rock listener pays to enjoy is black-begotten.”Footnote ³⁴ In fact, in a footnote worth quoting from at length, Wallace effectively summarizes the mission of the contemporary white scholar embarking on whiteness-conscious studies of black culture:

These invocations of “admission,” “relativism,” “credibility,” and “outsider” status suggest a certain reverence for nonwhite cultural production and a pre-emptive response to the kind of antiwhite criticism that Wallace perceives to be coterminous with rap music: “The Great White Male,” he suggests, “is rap's Grand Inquisitor, its idiot questioner, its Alien Other no less than Reds were for McCarthy” (24).

Consistent with his evident racial self-consciousness – elsewhere Wallace acknowledges himself to be “resoundingly and in all ways white” – Wallace's musings on rap defer at several points to an anti-intellectual methodology that privileges feeling over thought.Footnote ³⁵ Viewed from this perspective, the aforementioned oral quality of the work may also be read as an acknowledgement of the authors' own “rare white” entitlement to discuss rap and an attempt to downplay their “pre-Ph.D.” position of privilege by presenting the material as “less what we knew than what we felt, listening; less what we liked than why” (23, emphasis added). This strategy provides appropriate accompaniment to the “goofy gaffes” and “nutty, ballsy freedom to riff and explore” that Soderberg praises in his review of the book.Footnote ³⁶ Wallace's playful attempt at racial inversion culminates in an anecdotal experience of “invisibility” that, in such a race-sensitive context, cannot help but recall the narrator of Ralph Ellison's Invisible Man. Wallace chronicles the experience of attending a rap concert at Madison Park High as a white undergraduate in terms reminiscent of Ellison's existential “invisibility”: the “audience who turned out to see the Returning Ruler … didn't hassle or abuse us. Actually it was worse. They acted like we weren't there.” Wallace marvels at the fact that he and Costello “didn't even qualify as interlopers: we were so conspicuous we were invisible” (49, emphasis added). Beyond a loose affinity with Ellison's narrator, whose physical blackness serves as a barrier between his humanity and the compassion of the world in which he lives, Wallace's incredulity at going completely unnoticed, at being so incongruous as to be completely irrelevant, also recalls William S. Burroughs's own adoption of the invisibility motif during his years in Tangiers – a parallel tale of the bemusement with which whiteness confronts the conditionality of its reception.Footnote ³⁷

Wallace's strategically self-conscious approach to rap's blackness – and his own whiteness – does not always pay off. The surprise with which Wallace interprets his irrelevance or “invisibility” reads, in the present context of rap and race, as an overestimation of the importance of antiwhiteness to rap's particular presentation of blackness. Our suggestion, however, is that the essay's overwhelming focus on race – the allegedly irrevocable blackness of rap and the irredeemable whiteness of Wallace and Costello – signals not only intellectual and cross-cultural earnestness but also a keen interest in the project of “making whiteness strange” that Richard Dyer would, seven years later, establish as essential to the progression of American racial ideology.Footnote ³⁸ Wallace's interest in rap, for all his ostensible mystification, is not at odds with, but rather dependent upon, his whiteness; it is, in his own words, an “uncomfortable, somewhat furtive, and distinctly white enthusiasm” (21, emphasis added). The reader gets the sense, as the authors continue to marvel at what they evidently deem their atypical affinity for rap music, that their foray into rap criticism is intended to signal their potential positionality “outside” the same humdrum whiteness they lampoon throughout the book. Wallace's tendency to self-consciously parody the “Yuppie” whiteness he embodies (“the urban-crisis stats that make us grimace over our morning croissants” (43)) is more than overshadowed by repeated assertions of a strangeness rendered credible by the fact that rap's “appeal for 2 highbrow upscale whites was just plain incongruous” (23).Footnote ³⁹

Bearing in mind that to apply a postmillennial understanding of the relationship between rap and race to Wallace and Costello's twenty-three-year-old text would be anachronistic, it should be noted that their dramatic assessment of the role of whiteness in rap is, at least, contextually sound. Rap's gangsta period, from the late 1980s to the early 1990s, was by no means exclusively preoccupied with the symbolic opposition between Wallace's “Yuppie” whiteness and gangsta's own ghetto-centric brand of blackness, but it undoubtedly heralded the terms of racial authenticity that continue to pervade hip-hop culture today. The Los Angeles riots of 1991, ensuing in part from the infamous scenes of police brutality inflicted upon Rodney King, effectively symbolize the moment of social crisis from which gangsta drew its momentum. In turn, media sensationalization of the genre's frequent lyrical attacks on police and other official authority figures inevitably heightened the rebellious significance of the music to mainstream America. Eithne Quinn, author of the important hip-hop study Nuthin’ But a “G” Thang: The Culture and Commerce of Gangsta Rap, contends that, contrary to Wallace and Costello's reading, the “undeniable pleasures” of rap's thematic investment in danger and difference “may have been overstated by critics,” and that “much of gangsta's appeal stemmed from shared, youthful, masculine pleasures rather than the ‘othering’ of racial difference.” Quinn acknowledges, nonetheless, that amongst gangsta's founding objectives are to

In Spectacular Vernaculars: Hip Hop and the Politics of Postmodernism – one of the few studies to acknowledge Wallace and Costello's work – Russell A. Potter derides the duo's approach to rap as “canny ‘insider’ posing” and draws attention to their failure to incorporate an understanding of the “signifying monkey” trope from which the book's title is derived. At times, Potter's brief dismissal of Signifying Rappers evinces derision and skepticism:

Potter quite reasonably describes the authors as problematically “titillated” (84) by their acknowledged fear of rap's dramatic violence and “closed” (84) blackness. His critique also situates such misreading of rap's vernacular play within the framework of the signifying monkey itself, whereby the white man (symbolized by the Lion, the self-designated “king of the jungle”) is outsmarted because he does not understand the “serious unseriousness” of the black man's wordplay:

Wallace and Costello's ambivalent response to rap's violent content and the extent to which this renders the music “antiwhite” reflects, certainly, a failure to engage with the art of signifying as thoroughly as they might. However, Potter's wholesale dismissal of Signifying Rappers willfully ignores the fact that the book is as much concerned with establishing rap's important place in the postmodern cultural canon as it is with questions of racial positionality and, in fact, covers much of the same ground as Potter's Spectacular Vernaculars – five years earlier. Potter is right to challenge the often awkward treatment of race, especially the white–black tension, in Signifying Rappers, but the essay's quite clearly embryonic attempt at whiteness analysis should not overshadow or nullify its expert assessment of rap's postmodern potential.

Potter's critique does, nonetheless, identify what is arguably the crucial problem with Signifying Rappers from the perspective of contemporary whiteness criticism. For Wallace, the role of whiteness in rap is manifested in the white listener's experience of fear. Unlike his earlier commentaries on the imperative separation of author and subject when writing on rap as a white listener, Wallace's veritable revelry in the disturbing aspects of violent and racially provocative rap in the body of his essay is at odds with contemporary whiteness methodology. He points to fear as the vital connection between the “rare white at the window” (30) and the ostensibly unavoidable blackness of rap, a fear he characterizes in his “outsider” rap concert anecdote as “a kind of delicious enforced paranoia” (42) that he shares only with the white police officers also in attendance. The thrill of rap's symbolic danger, according to Wallace, rests heavily on its commitment to remaining “closed, prepositionally black, Other”: rap “can and must remain a cutting edge … the only kind of edge We fear, anymore, at all” (34, original emphasis). The possibility that rap is not designed to thrill the white listener with the deferred threat of violence, crime, and other horrors characterized by the increasingly mythologized ghetto space is, incredibly, proffered as the suspected “root and hidden white mainstream fear” (45). Wallace asks, “what if cutting-edge rap really is a closed music? Not even pretending it's promulgating anything controversial or even unfamiliar to its young mass audience? What if rap scares us because it's really just preaching to the converted?” (45) Although these anxieties relate in clear ways, as we have outlined, to Wallace's fears surrounding the impenetrability of avant-garde poetry and fiction, on a literal level this line of questioning perpetuates the common conservative critique of gangsta rap, wherein the central concern is the extent to which its violence-driven narratives are “serious,” to borrow Wallace's term. At this point, the book's confrontation of positionality and entitlement slips into an existential crisis of sorts, in which the “hidden fear” of the “white mainstream” consumers of rap is the possibility that it has no interest in white people whatsoever; that for “serious” rap, the white listener need not exist.

It would be imprudent, ultimately, to dismiss Signifying Rappers on the basis of its more troubling fantasies about the relationship between whiteness and rap. Wallace's approach is not, after all, a formal venture into critical whiteness analysis as we know it today, but rather an explorative, tentative, and quite concertedly self-effacing attempt to engage with the material in an unprecedentedly race-conscious way. As this article has outlined, the book contains numerous provocative and incisive interpretations of rap's cultural power; nearly every page contains an illuminating reading of some aspect of hip-hop production and reception. The problem with Signifying Rappers, from a contemporary whiteness-studies perspective, lies not in its positionality or methodology per se but rather in the inconsistency of its aims. Wallace and Costello oscillate between musicological analysis and cultural commentary, admissions of inadequacy, and bold assertions of near-mastery: “Perhaps the purview of the outsider alone is pretty much the only way to subscend rap's yes vulgar Alien surface and hear this pathos” (122). By and large, the book demonstrates impressive and thoughtful appreciation of rap and the culture that it both stems from and perpetuates: Wallace memorably describes rap as “a kind of metaphor-with-larynx for a subbed-culture unique in its distillation of the energy and horror of the urban American present” (47) and prophesies its potential to improve black American literacy. He also argues that rap deconstructs the “bourgeois-less economics of the '89 ghetto” through a sustained critique of 1980s Reaganism, wherein “the best rappers both exemplify and ridicule the contradictions inherent in 80s conservatism, in mixed images of political democracy and economic Hobbesianism” (126). These latter theses indicate Wallace's interest in the import and impact of rap as a cultural force in the broader American context, as much a product of particular social phenomena (Reaganomics, “white flight,” and the changes ushered in by the crack cocaine trade) as a potentially leading instrument in political change and the evolution of the social status quo.

These early and ambitious attempts to address race as a white American writer are highly instructive in considering Wallace's subsequent career. His fiction, particularly Infinite Jest, reveals a writer committed to recording both subtle and unsubtle forms of racism: there are numerous occasions in which characters use racist epithets, such as “nigger” (857), “Orientoid tongues” (767), “chinkette” (728), “coloreds” (1054), “bugeyed fucking spic” (533), and “Orientals” (467). Almost all these examples are taken from passages in which Wallace uses free indirect discourse, and thus are clearly distinct from the narrator's voice; in addition, after one such instance of the word “nigger” (857), Wallace emphasizes this distance by directing the reader to an endnote that simply reads “Sic” (1026).Footnote ⁴³ However, one particular line from the novel, taken from a long section in which the narrator (clearly a proxy for Wallace himself) details the “many exotic new facts” (200) he has acquired during his time at a halfway house, reads as more directly autobiographical: “That black and Hispanic people can be as big or bigger racists than white people, and can get even more hostile and unpleasant when this realization seems to surprise you” (200). Importantly, the “this is how” section of Infinite Jest (172), in which Hal narrates Mario's Tennis and the Feral Prodigy, owes a clear debt to Jamaica Kincaid's much-anthologized prose poem “Girl,” and indeed can be read as a white middle-class retelling of Kincaid's text.Footnote ⁴⁴ Moreover, in his 2001 essay on American usage, Wallace wrote about his in-class explanation of the differences between “Black English and White English” – an explanation, he notes, that resulted in “more than one colleague profess[ing] to find my spiel ‘racially insensitive’” – and the “official complaint” lodged by one “black undergraduate” who was offended over Wallace's account of such usage differences.Footnote ⁴⁵ Although his essay goes to great lengths to mount what is, for the most part, a convincing justification for such a “spiel,” his speech is nevertheless somewhat clumsily phrased and, as he later admits, “rhetorically naïve” about the complex investment of identity within politically marginalized usage.Footnote ⁴⁶

Given that 2013 marks the first republication of Wallace and Costello's Signifying Rappers, the significance of the text as a preliminary investigation into rap and whiteness merits attention. The authors' freewheeling analysis and the undeniably problematic outcomes of their investment in race throughout Signifying Rappers should not override the seminal, groundbreaking – though, as previously noted, somewhat embryonic – nature of the text. In addition, the book's more problematic elements, far from rendering it dismissible or embarrassing, reveal how much the disciplines of whiteness and hip-hop studies have evolved over the last twenty-five years. As for the more specific disciplinary concerns of Wallace studies, Signifying Rappers deserves closer attention for its revealing – and all-too-frequently overlooked – glimpse into Wallace's idiosyncratic literary prose style. The varied and often experimental linguistic techniques used throughout Signifying Rappers highlight the broader arc of Wallace's literary development and foreshadow later textual strategies. Furthermore, when read closely, the text offers an oblique, though revealing, vision of Wallace in the process of attempting to articulate an artistic vision that would respond adequately to both the legacy of postmodernism and the particular demands of the cultural present. That the book was written at a juncture in which Wallace was “terrified to write fiction” (213) shows just how pressing such an articulation was. Ultimately, far from a mere curiosity piece in Wallace's corpus, Signifying Rappers documents the particular intersection of white America and blackness engendered by rap's “gangsta” moment, a historical juncture that continues to influence pop cultural interpretations of race and hip-hop some twenty-five years later.