Friday essay: weirdly old-fashioned and wildly uneven – David Foster Wallace’s Infinite Jest at 30

Thirty years ago, living in Cambridge, England, I wandered into Heffers Bookshop and picked up a monstrous new novel on the display table. It had a title out of Hamlet, a Simpsons-sky dustjacket, hundreds of endnotes, and ran to almost 1,100 pages. Infinite Jest occupied much of that cold February and March, and to this day I remember finishing it with a sensation of frustrated exhaustion.

It seemed then (as it does now) a wildly uneven book held together by something new in American fiction of the postmodern age: a white-hot purity of moral purpose that made it seem weirdly old-fashioned, despite all the bells and whistles of its cumbersome near-future satire about a nation amusing itself to death.

It was, undoubtedly, a major achievement, though it was also clear that something was not quite right with its writer, David Foster Wallace. Aesthetic misjudgements had led to so many wincing misfires, lapses of taste and tedious longueurs that it all seemed indicative of a deeper subjective disequilibrium.

In that sense, the book was “true” in a way the author’s journalism (to which one turned with curiosity) was not. In those snappy features, written for Esquire, Rolling Stone, Première and other glossy magazines, the ardent moral vision is worn as a winning professional mask. It speaks in a voice mixed of pedantry, whimsy and stern judgement.

Smart, alert, observant, mordantly funny, the Wallace of the non-fiction also came across as a bit of an asshole. And an asshole, it turned out, he was. But more of that later.

Literature of exhaustion

Twelve years later in 2008, Wallace was dead at age 46. That suicide has subsequently woven something of a halo over the bandanaed-average-Joe-nice-rural-Midwest-boy image cultivated by the author while alive. Posthumous books, a film and a veritable industry of critical approbation have only contributed to his cult status.

Today, Wallace lives online as a saintly, almost Buddhist YouTuber, dropping bromides and sallies of wisdom, looking always earnest and sincere, if not clean-cut. It is a sad fate for a writer who, at one point, was the great hope of American letters.

What are Wallace’s claims to our attention today? And what of Infinite Jest itself, the work by which he will and should be judged, on which he worked on and off for a decade? What have 30 years done to that achievement?

In part, his place in literary history is defined by his generational position. Wallace was young enough to be the child of those postmodern giants who defined the age of his youth and at whose feet he sat: Don DeLillo, John Barth, Donald Barthelme, Thomas Pynchon. He could play the ardent freshman to the decadent sophomore Brat Pack who had carved out the early-1990s American scene: Bret Easton Ellis, Tama Janowitz, Jay McInerney.

This rivalry rears its head in Infinite Jest, where Ellis appears in a rollcall of authors of “depressing books”. What was wrong with this second generation of postmodernists for Wallace was they took it all too far. They wallowed in unearned metafictional irony, drug-addled blankness, disaffection and spoiled anomie, while outside the real world just got worse. They proved that postmodern fiction – what Barth called the “literature of exhaustion” – was itself exhausted. Something had to be done.

Infinite Jest was that something. But it was so in a deeply conflicted way. The best way to consider it is as a kind of geological cross-section of a writer and a literary culture at a moment of major upheaval.

The outermost layers are still flashily “postmodern”, but as we work our way deeper into the book, another mood emerges. What would be called the “new sincerity” gestates in the womb of Infinite Jest and emerges fully fledged by the end; its legacies are very much with us today.

Fancy and imagination

No self-respecting literary Wunderkind of the mid-1990s looking to unleash a mega-novel could help but vie with Pynchon, Barth, William Gaddis and Robert Coover, while nodding to DeLillo. And so, Infinite Jest comes with all sorts of postmodern ingenuities and hyper-connectivities, recursive mediated mise-en-abymes and madcap political conspiracies.

As in Wallace’s first novel, The Broom of the System, this dimension of his major work has always felt strained, insincere and unconvincing. Alongside the churning unease of DeLillo’s Libra, Wallace’s conspiracy of Quebecois wheelchair militants reads like boilerplate bestseller trash. His pastiche of Pynchon is so jejune he steals the Goethean Brocken Spectre phenomenon from Gravity’s Rainbow. Any reader of serious science fiction turns away in embarrassment from Wallace’s O.N.A.N., the Great Concavity, sponsored years, and all the other features of his thinly imagined near-future.

So much for the postmodern genuflection. Or not quite. Because this plot business bears more of a structural load than first appears.

Infinite Jest is offered in a formally disjointed, radically broken-up manner, both chronologically and in relation to its heterogeneous subject matters. Given that the two dominant strands of the book are resistant to plot – indeed, they turn programmatically against it – all the higher-order organisational responsibilities fall to the political conspiracy and its MacGuffin, the “Entertainment”. Stripping the latter away would remove the book’s skeleton and leave it to the fate of a beached whale.

Peeking ahead, we might say that Wallace’s unfinished novel about the US Internal Revenue Service (IRS), The Pale King, was unfinishable precisely because it made no concession to the cynical need for a plot. My feeling is that Wallace was essentially a short-story writer – a feeling vindicated in his fine collection Oblivion – and that plot was a labour for which he had no real talent.

I have come to think of this in terms of Coleridge’s distinction between Fancy and Imagination. Fancy is the mechanically associative energy that weaves collages out of existent materials; Imagination the creative power that disassembles and reintegrates reality into new and powerful unities.

There are few writers with a more prodigious Fancy than David Foster Wallace, who suffered from a weak and synthetic Imagination.

The ‘Substance’

The heart of this mammoth book is in the structural oscillation between two adjacent institutions in eastern Massachusetts: the Enfield Tennis Academy and the Ennet House Drug and Alcohol Recovery House. The staff and boarders at these two facilities, their respective backgrounds, organisation, funding, operations and missions, are vastly detailed over hundreds (and hundreds) of pages.

Two characters emerge as dominant: Hal Incandenza, the tennis prodigy and academic genius, and Don Gately, a lovable break-and-enter lowlife and recovering addict. They never meet. Relations between their respective institutional homes remain implicit throughout.

The bulk of the novel sits with Hal. And who is Hal? Shakespeare’s young prince? Kubrick’s onboard computer? Really, he’s a bit of both. Hal is a familiar figure in the annals of American literature, the subject of a bildungsroman that somehow fails to gel, that fizzles out around the protagonist’s inability to do anything at all: Holden Caulfield for Gen X.

Hal is the subject of great promise, of almost infinite potential (a handsome intellectual jock), who, when faced with the prospect of actually becoming an adult, coils up inside himself and withdraws from any meaningful engagement. The young prince become an automaton, a loose string of glitchy coded responses.

The centrality of Hal Incandenza is a problem for the novel. Not only because so much of it seems like poorly reprocessed autobiography (Wallace was himself a tennis prodigy), but because this paralysingly self-conscious, troubled, solipsistic, narcissistic character acts as a kind of black hole in the text. Hal sucks in heat and light, but refuses to emit any.

This white male member of the WASP ascendancy in northeast America, from a wealthy family, well connected with the power elite, certainly suffers, and his suffering is emblematic of much deeper and wider problems in the culture. But he is in many ways not worthy of the exhaustive attention, something the text knows well and struggles to find a formal solution for.

His transformation into an affectless, asexual starfish is one moment of Wallace’s answer. The other is Don Gately and Ennet House. The components of the novel that treat of the facility’s lengthy Alcoholics and Narcotics Anonymous sessions, confessions, feelings of attraction and repulsion, loosely assembling all the novel’s absurd plot complications, are its most ambitious and enduring achievement.

The existential, psychological, and emotional costs of dealing with addiction – with the “Substance”, in all its motley forms – are detailed with immense, painstaking care, in what sometimes feels like a documentary, fly-on-the-wall, round-eyed stare into the abyss. It is here that the figure of Don Gately swells into prominence as the counterweight to Hal’s adolescent black hole. He is a big, loving, imperfect bear of a man, emitting care and empathy, opening himself to loss and rejection.

The ‘Entertainment’

The “Entertainment”, the book’s implausible MacGuffin, is a film so compulsively watchable that it effectively transforms anyone who sees it into a drooling vegetable. It is the epitome of the various substances – chemical, commercial and cultural – with which the novel’s hundreds of addicts contend.

That it is produced by the founder of the tennis academy, sought after by the wheelchair terrorists as a super-weapon, and acted-in by one of the chief characters, makes it too hot to handle, a radioactive Grail element in the text.

What does it allegorise? Wallace’s thesis is as follows: American consumer capitalism doth make fools and addicts of us all. Hooked on the lowest common denominator and the dopamine hits of celebrity and fame, not to mention actual drugs, Americans are fast degenerating from their postwar high.

On the one hand, this leads to bad citizens, failing in their civic responsibilities and duties to protect the republic against internal decay. On the other, it leads to unhappy subjects, miserably disappointed and seeking the next escapist high. Corporate elites, oligarchs and tech bros are scooping up the financial rewards of this abject dejection. Government has fallen into the hands of advertisers and lobbyists.

If there is any resistance to this conspiracy of addiction-culture, it is through individual detoxification. By learning to be bored again, to sit lonely in rooms, care for the self through reflection and art, we undertake the tedious, unpleasurable task of rehabilitation. Becoming bureaucrats of the soul, we contribute to an overall lifting of the level of culture and filter our pleasures back through the social contract.

A rehab clinic serves as the most fitting allegory for the kind of collective work we need to do; the “Entertainment” is its sworn enemy.

The fixed terms

“We all suffer alone in the real world,” Wallace once said; “true empathy’s impossible.” These are the fixed terms of his art, and of the “new sincerity” itself.

The postmodern offended him because it seemed to have capitulated in advance to the wickedest tendencies of the culture. What we needed was a literature that could fashion a plausible enough verisimilitude of empathy, sufficient to keep its hope alive in the howling snowstorms of contemporary nihilism.

Wallace was an old-fashioned American conservative. He voted for Reagan’s second term and venerated Republicans like John McCain. He had no sense of politics as a passionate collective struggle over resources and values. The values were already consecrated in the US Constitution; it was bad actors who were gobbling up too many of the resources – not a class enemy.

Like Cormac McCarthy, Wallace was a serious moralist with zero political vision: witness the cynical collapsing of Left and Right in Infinite Jest and the witlessly two-dimensional image it presents of collective commitments beyond a functioning bureaucracy.

Wallace’s interest rests with the individuals who suffer the consequences of a rapid dismantling of the hard-won cultural consensus of the postwar pax Americana. Their misery, their exploitation by interests that care nothing for psychic cohesion, real personal choice or emotional fulfilment, is his only true concern.

At Wallace’s funeral, DeLillo said: “He wanted to be equal to the vast, babbling, spin-out sweep of contemporary culture.” But did he? He seemed blind to the gathering forces of much that has been inspiring about that culture since: Black Lives Matter, antifa, queer and trans activism, and of course feminism.

Wallace’s women are, well, a problem. Like Salinger, McCarthy and Updike before him, he knew how to do men, especially younger ones, but his women are lamentable. Avatars of the polymorphously perverse and brilliant women of Pynchon, Philip Roth and Saul Bellow are sketched in, but with woeful incompetence. You get the sense that if he’d ever read any Adrienne Rich or Audre Lorde, it might have killed him.

There is an interview with Charlie Rose (remember him?) where Wallace casually observes that, unforgivably, “females” just don’t like Clint Eastwood’s Unforgiven. “Females.” What’s with them?

The lethal Entertainment, it turns out, features one such “female”, an impossibly attractive one in a white gown, leaning into a crib and mouthing the words “I’m so sorry” – as if the most blissful thing imaginable were a female’s apology for the crime of having given you birth, separated from you, and then cock-teasing you for the rest of your life, before killing you off.

The woman playing this Madonna says of herself: “I’m perfect. I’m so beautiful I drive anybody with a nervous system out of their fucking mind!” She wears a veil as a favour to the world of men whom she would otherwise disable by virtue of being “perfect”, whatever that means.

The uninterrogated assumptions at work here amount to a kind of “incel” misogyny. As for the rest, Megan Garber has observed, “women’s stories get treated as one of Wallace’s trademark footnotes might be: decorative, dexterous, whimsical, trivial. Pretty afterthoughts. Optional.”

The #MeToo revelations by ex-girlfriend Mary Karr that Wallace was obsessively predatory, violently combustible, a stalker and a serial disposer of young groupies, have rocked his reputation to the extent that Yale professor Amy Hungerford posted a withering article about “not reading Infinite Jest” and the Guardian published a story that claimed “reading the ultimately heartless and intellectually empty Infinite Jest was the biggest waste of a summer I ever spent”.

Is that right? It is always best to make literary judgements on the basis of reading.

I’ve slogged through Infinite Jest twice (so you don’t have to!) and my critical sense that it is not a good book has only been confirmed. There are good things in it, but they are drowned out by noise, a truly exasperating authorial style, ridiculous plot elements unworthy of serious fiction, and an ambient misogyny. One finally wishes for a violently edited, 250-page collection of short stories that focused on the addicts of Ennet House.

A year later in 1997, I returned to Heffers to buy a copy of the long-awaited Mason & Dixon by Thomas Pynchon. Here, it seemed to me then and has seemed to me every day since, was a novel so incandescently great, so towering and substantial, so rich with imagined worlds and teeming with political implication, that Infinite Jest must disappear forever in its shadow. Yet Infinite Jest is the book that has exerted by far the greater influence over the course of literature since, for better or for worse.

Julian Murphet does not work for, consult, own shares in or receive funding from any company or organisation that would benefit from this article, and has disclosed no relevant affiliations beyond their academic appointment.