Wallace came of age in Champaign, Illinois, where his father was a professor at the state university. With its elegant restaurants and lively bar scene, the college town acts as a commercial oasis in a pastoral sea. Wallace spent much of his adult life not far from Champaign, in Bloomington, another mid-sized city. It is here that he taught literature and creative writing at Illinois State University, and where he lived when he wrote many of his most profound stories, essays, and books, including his wild and gigantic masterpiece, Infinite Jest.

Bloomington is in central Illinois. Even if it’s only 130 miles from the bright Chicago lights, it could be in another sociological universe. Farms and barns decorate the landscape, as the highway slices through fields of grass and Indian plantain, and, as Wallace puts it, “the corn is as tall as a tall man”. Much like Champaign, Illinois State University gives Bloomington a separate identity from nearby villages, as does its status as a company town: it’s home to State Farm Insurance, which employs 67,000 people and brought in $5.7 billion last year.

The mid-Midwest contains contradictions, even in its appellative cliches. The region is the “Heartland”: where everyone from culture-war reactionaries, to nostalgic Leftists dreaming of the resurrection of the manufacturing base, locate their hopes for the country. Yet these vast flatlands are also “flyover country”: not so much politically, as both parties pander for its votes, but culturally. In the Midwest, and especially its rural hinterland, it is easy to feel as if New York and Hollywood, the cultural capitals of the republic, rotate in separate solar systems.

Taken together, this contradiction creates what Wallace referred to as a “brotherhood of loneliness” — detachment from the dynamism of American society, detachment from what one imagines as the discourse that directs social progress or societal decline. Despite his eventual return to the Midwest, the author confessed to resenting his “physical place in the great schema” when leaving for New England. Those who remain can feel a wide range of emotions, from bitterness to pride, but they are either bitter or proud about, as Wallace put it in his 1993 essay, “being away from it all”.

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Did David Foster Wallace predict the future?

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The vast barrenness, oceanic flatness, and dot-on-a-map desolation was overwhelming when my wife and I, on a recent road trip to Bloomington, stopped 20 miles away in Pontiac for lunch at a Burger King. Aside from a few gas stations and fast food competitors, the windows of the restaurant offered angles on nothing. A couple of steps down from the soda fountain and waste basket, there was a table fit for one with an unused chair. Adorned in a white tablecloth, and decorated with an empty plate, clean silverware, and a folded American flag, it was a tribute to the “members of our Armed Forces missing from our ranks.” “The Missing Man Table,” as it is called, “symbolizes that they are with us here in spirit.”

It was like an image out of a David Foster Wallace story — a sad expression of deep, human loneliness, but as so often, not without a counterpoint. It is inside a franchise of an industry not exactly revered for its social conscience, and smack dab in the middle of garish advertisements for sugary and high-cholesterol food products, paper Burger King crowns, and palpable boredom and dread of low-wage workers. “The Missing Man Table” is an attempt at sincere, human connection, something Wallace cared and worried about, in an environment of commercialized entertainment, something he feared would devour the decency of his country and the dignity of his countrymen.

Wallace’s prescient concerns were clear in Infinite Jest. The novel’s biggest threat is something called “The Entertainment”, a video so hypnotically entertaining that it reduces even passive spectators to a catatonic state. Social media and smartphone addiction have degraded human life and community in ways that make “The Entertainment” sound plausible. More than that, though, Wallace wrote many essays and stories, on topics ranging from pornography to John McCain’s 2000 presidential campaign, about how our bottomless appetite for entertainment, and technology’s ability to feed it, would transform the social compact, civic virtue — and any idea grander than momentary self-interest — into punchlines. The Pale King, his posthumously published novel about the IRS, which is mostly set in Peoria not far from Bloomington, presents public accounting as heroic: precisely because it is so boring. To overcome boredom, the novel suggests, is to open possibilities of sacrifice and service in the name of ideals that transcend momentary fixations of pleasure.

Given that everything has become entertainment, the social compact has been butchered by individualism and tribalism, and Donald Trump, a more vicious version of Infinite Jest’s ignorant lounge-singer-turned-president, is in the White House once more, the timing was perfect to visit Wallace country. After all, it is right in the middle of Trump country.

McLean County, home to Bloomington and its university, barely went for Kamala Harris, with the Democratic nominee earning 50.9% of the vote. Sections of Bloomington itself, however, supported Harris by margins ranging from 27 to 52 points.

But around the town is a sea of red. Its bucolic villages supported Trump by equally large margins as Harris’s support in the heart of the college town. The inversion of the vote captures the extremity of American division, making Barack Obama’s bromide regarding the “purple states of America” look like a bruise on the country’s fractured psyche.

As the endless bloviation about the severity of America’s political divisions imply, the ideological voter is himself creeping towards loneliness. Like no other period in recent history, political arguments sour friendships, tear apart families, and “sort communities”, in the words of Texas journalist Bill Bishop, into Left and Right. In a classic chicken-or-egg conundrum, one could ask if the loneliness that Wallace identified at the heart of the Midwest, and America more broadly, is responsible for this polarization, or is the polarization enhancing the loneliness?

Wallace’s diagnosis did not spare his own kind, the highly educated middle and upper classes of Gen X. He often wrote about the poisonous influence of the ironic detachment as a response to nearly everything. Those whose first instinct is to smirk and drop a witty one-liner in the face of tragedy or scandal will also find themselves unable to form deep social bonds, while also rendering themselves incapable of investing in a story or political project that transcends their own short-term desires.

In an essay about 9/11, written from Bloomington, Wallace describes walking over to an elderly woman’s house to watch “the Horror” on television. He feels a “sad” and “lonely” separation from “Mrs Thompson”, crying and praying in her modest ranch home. She has an innocence, Wallace writes, that he cannot himself entertain. He soon notices, for instance, some of the media’s cynical marketing ploys — every anchor has rolled up his sleeves — whereas Thompson and her prayerful friends take everything as presented. “Part of the horror of the Horror,” he explained, “was knowing deep in my heart that whatever America the men in those planes hated so much was far more my America… than it was these ladies’.”

Even on 9/11, Wallace was able to intuit that national tragedy would fail to unite people whose experiences and beliefs so vastly differ. The quiet separation that Wallace depicted would eventually morph into foaming-at-the-mouth hostility during the Covid-19 pandemic.

There is no way of knowing where the falsely named Mrs Thompson lived. Wallace identified her as a woman from his church — but by “church” he was obscuring the fact that he belonged to Alcoholics Anonymous. Their meetings took place around the corner from his house, at St. Michael’s Episcopal Church, a small house of worship with a fountain and flag outside. As for Wallace’s own home, it certainly doesn’t look like the place where someone would write one of the greatest American novels of the last century. It is currently occupied, but there is no acknowledgment that Wallace once lived inside. The same is true of his former office at ISU, which even now lacks a sign, photo or plaque commemorating his memory.

In a sense, that anonymity feels appropriate. “David felt safe here,” says Victoria Harris, a retired ISU English professor who was close friends with Wallace. Harris tells me that the author liked being close to his parents, and establishing good relationships with his students, but also that he enjoyed “being away from it all”. She adds that he preferred living in a quiet, “middle class” neighborhood — as opposed to more luxurious subdivisions nearer the city center. “I don’t pull an aw-shucks-regular-guy thing,” Wallace himself once told an interviewer, “[but] I treasure my regular guy-ness. I’ve started to think it’s my biggest asset as a writer.”

Wallace was in a unique position to use art and journalism to make sense of Middle America’s collapse into partisan rage and a mindless addiction to scrolling. The fact that he wrote a masterfully experimental novel from a tiny home in a normal Midwest neighborhood captures yet another duality in his work. Unlike most contemporary literary fiction, he didn’t write about the insect politics of Brooklyn, further pulling the art form out of the window of relevance of most Americans. At the same time, though, he enjoyed the reverence of the New Yorker set, giving him the potential to communicate to two different audiences.

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Yet as his absence at ISU implies, there is always the possibility that, had he not taken his own life in 2008, his country would now ignore him. America’s lack of cultural memory, and its continual erasure of history, creates a fragmented present where shared meaning is impossible to cultivate, and the dull hum of loneliness resonates from college campuses to roadside restaurants.

In recent years, journalists, scholars, and even Hillary Clinton have become worried about America’s “loneliness epidemic”, arguing that it fuels political militancy, undermines social cohesion, and contributes to violence. It feels utterly appropriate, therefore, that one of Wallace’s most popular ideas was that literature can and should make readers feel the spark of human connection. “I don’t know what you’re thinking,” he once told an interviewer, “but a piece of fiction that’s really true allows you to be intimate with a world that resembles our own in enough emotional particulars so that the way different things must feel is carried out with us into the real world. I think what I would like my stuff to do is make people less lonely.”

This, then, was a prophet of that deep American predicament, writing in his novels, stories, and essays about people, real and imagined, who separate from those around them and even the best parts of themselves. He linked their loneliness to misplaced priorities of attention, whether “The Entertainment” in Infinite Jest or the talk radio of the Nineties that attracted millions of listeners throughout the US, and was particularly popular in the rural Midwest — a medium of political infotainment that he ridiculed as “deeply, totally populist” but also “completely fake”.

As for Wallace himself, campus invisibility might also be explained by posthumous domestic violence allegations from his ex-girlfriend, Mary Karr, who claims that he stalked and once threw a coffee table at her. Because he is dead, of course, Wallace can’t offer his side of the story. One of his best books, a collection of short stories, mainly about misogyny, Brief Interviews with Hideous Men, inevitably leads one to wonder if he battled his own demons, demons that brought pain to others, and would surely have made himself and others lonelier. Yet another irony, in a town and region full of them. In any event, now that Wallace is missing from our collective table, we’ve merely left room for more corporate chow, and fragile paper crowns.

I was a bratty, bookish 15-year-old when it was published in 1996. A 1,000-page-plus novel bloated with endnotes that have their own footnotes was an irresistible challenge. David Foster Wallace was not an obscurantist in his own literary taste — he taught Stephen King and Thomas Harris at Illinois state university — but Infinite Jest is a book at bloody-minded war with its own bookness. With its maddening excess of information that you must hold in your hand as best you can, it feels more like trying to absorb the internet than reading a regular novel.

As well as being attention-repellent, it is also sometimes just repellent. There are scenes of comedically extreme horror: a woman dying after the handbag that holds her artificial heart is snatched from her, a man dying in his own filth while obsessively watching reruns of M*A*S*H, a dog dragged behind a car until all that’s left is a leash, a collar and a “nubbin”. Before livestreamed mass shootings and animal cruelty for clicks, Wallace knew that the grisly and grotesque was what the public wanted.

He did not see the future. But he saw the forces shaping the future, and understood the ways they would deform people in turn. 

In an aside, Wallace writes about how, with the introduction of the “Teleputer” (what we would call a laptop), video calls enjoyed huge popularity, followed by dramatic decline. Users quickly discover that being seen is enormously anxiety-inducing, partly because it means you must visibly be paying attention to the other party at all times, partly because you must also pay attention to how you look when making a call.

The answer to this anxiety is, first, “high definition masking” — a flattering composite of the user’s face digitally overlaid on the screen. Then comes actual masking — hyperreal rubber versions of the user’s face that can be quickly strapped on for calls. Eventually, in response to this “stressfully vain repulsion at their own videophonic appearance”, consumers revert to audio-only, which is now “culturally approved as a kind of chic integrity”. 

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Porn will destroy you

By Sarah Ditum

This divide between the real and the represented has been borne out by our experience of Zoom, Instagram and TikTok: filters are now so advanced that they can be applied to moving images, and you can digitally beautify yourself while livestreaming. Only instead of resorting to rubber masks, we remodel the flesh itself: “filter face” tweakments, intended to bring the human closer to the digital ideal, are on the rise. Wallace was right about the way pervasive exposure to our own image would break us. It’s just that the way we’ve responded is, somehow, even more dystopian than he imagined.

Infinite Jest’s near future is now our near past, and in 2008, Wallace killed himself after suffering decades of profound depression. By the middle of the next decade, his greatest novel had been recast as a byword for tedious white masculinity, the author himself cancelled. This was, at least in the biographical sense, deserved. In 1990, Wallace had met the poet Mary Karr. He was a resident in a halfway house, she was a volunteer, and he became obsessed with her. They dated, they broke up, then he assaulted and stalked her. In 2018, Karr tweeted that he had “tried to buy a gun. kicked me. climbed up the side of my house at night. followed my son age 5 home from school. had to change my number twice, and he still got it. months and months it went on.”

The novel includes multiple men in recovery steeping in the shame of their past violence, and it would be nice to imagine that this was Wallace examining his own conscience. On the other hand, it also includes a reciprocated love story between the large, lunkish, David-Foster-Wallace-ish character Don Gately, and the beautiful, idealised, Mary-Karr-ish Joelle van Dyne. Infinite Jest was, arguably, an implement of his ongoing harassment and should not be dishonestly mined for signs of redemption.

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Still, it is a very contemporary thing to demand moral purity in artists: the kind of impulse that, perhaps, comes from seeking simplicity when far too much knowing is possible. “What do we do with the art of monstrous men?” asked Claire Dederer, as though to be an audience is inevitably to be an accomplice. Good art can be made by people who’ve done bad things, and perhaps only a monstrous man can faithfully portray the outlines of his own monstrosity. Reading is not an act of worship, although one of the problems for Infinite Jest is that certain male readers have treated it as such. 

And so, Infinite Jest has plummeted from literary touchstone to confirmed red flag. In a viral tweet from 2020 listing “Top 7 Warning Signs In a Man’s Bookshelf”, the first item was “A dog-eared copy of Infinite Jest”. The “dog-eared” was important: it was the act of having read it, rather than posing as someone who might read it, that sounded the klaxon.

But unread copies could be equally alarming: when the actor Jason Segal bought Infinite Jest in preparation for playing Wallace in a film, he recalled that the female bookseller rolled her eyes and said: “Every guy I’ve ever dated has an unread copy on his bookshelf.” Nicole Cliffe made it number four on her catalogue of “Books that Literally All White Men Own”. 

I have never run into a “DFW guy” — they’re probably more of an American campus thing. But I ran into the “Philip Roth guy” at university and recognise the type: clammy, proprietorial, forcing his literary taste on girls in lieu of forcing himself. That I had read Infinite Jest felt vaguely embarrassing. All that effort, and it turned out the most high-status option would have been to not read it and then be glibly dismissive. 

It’s perversely appropriate that Infinite Jest ended up holding such a key place in the vocabulary of this irony-bound strand of performative feminism, because irony was one of the things that Wallace was both appalled and fascinated by. In a 1993 essay, he writes that “irony and ridicule are entertaining and effective, and that at the same time they are agents of a great despair and stasis in US culture.”

Infinite Jest isn’t above irony, but it often pits itself against irony. “It’s like there’s some rule that real stuff can only get mentioned if everybody rolls their eyes or laughs in a way that isn’t happy,” thinks one character. Another feels an “aftertaste of shame after revealing passion of any belief and type when with Americans, as if he had made flatulence instead of had revealed belief” (the weird syntax is because this character is Quebecois). When sincerity is untenable, it becomes easier to engage with symbols than things. 

Over and again in the novel, the “real” gets displaced by the representation, like the rubber faces that can replace flesh ones on video calls. One of the centrepiece scenes of Infinite Jest features a geopolitical strategy game called Eschaton — a kind of Risk, but played by teenagers with balls and rackets to stand for missiles. The game comes violently undone when the players start hitting each other and the referee can’t work out how to distinguish between the territory and the map. As for the M*A*S*H-obsessive, “crucial distinctions had collapsed” between the fiction and the real.

And maybe this is connected to the novel’s weirdly well-informed interest in transsexuality. The gender ideology that makes front-page news now was a niche interest in the Nineties, confined mostly to academic papers and message boards for transitioners. Wallace’s inclusion of a young, effeminate, gay, “gender-dysphoric” character and a middle-aged, masculine, straight crossdresser suggests a hefty familiarity with the sexology literature long before any of this had crossed into the mainstream — it’s effectively a thumbnail sketch of the influential theory, developed by Ray Blanchard in the Eighties and Nineties, that male transsexuality divides into “two types”, the autogynephiliac and the homosexual.

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But it also fits with the vision of an America where the signifiers that stand for “woman” hold more weight than the physical fact of femaleness. Gender as we experience it now — the idea of an “essence” or “true self” that renders the material body irrelevant — couldn’t have come to exist without the internet. Only when technology allowed people to present themselves as pure language, signifier unmoored from signified, did it become possible to believe that sex was malleable or unreal. Maybe transsexuality fascinated Wallace because he saw it as another way that humans confuse the symbol with the thing itself, the feminine with the female.

This summer, I started rereading Infinite Jest, mostly out of curiosity. It is, still, a very annoying book. But there’s something I didn’t understand about it in 1996 that I do now I’m older than Wallace was when he wrote it. He saw American culture as an exhausted force, trapped smirking in a hall of mirrors. And he saw that getting worse as screens extended their influence.

One of Wallace’s influences, Thomas Pynchon, wrote stories about the technology that made America possible: geographical surveys (Mason Dixon), the postal service (The Crying of Lot 49). Infinite Jest is about the technology that could undo a state: a kind of entertainment so compelling that it turns consumers utterly away from reality. It asks whether the real, or something like it, might be worth recovering. 

It is, still, a difficult book — and difficult in new ways. The wheedling presence of my phone is competition that Infinite Jest never had to contend with the first time around. The disturbing fact of Wallace’s own bad acts, too, was not available to me in the Nineties, and even if it had been it probably wouldn’t have struck me as a problem for the novel. But the difficulty is, and always has been, the point. Of course Infinite Jest could be shorter, lighter, less infuriating. But if it’s heavy, it’s because it’s weighing you back down in the physical world.

Something of an obsessive, he had an unhealthy relationship with women, often fixating upon a particular romantic attachment. He tried to join the Roman Catholic church twice, but both times he couldn’t quite bring himself to do it. He loved stray dogs. May he rest in Peace.

My own interest in Wallace was sparked by a brilliant graduation address he gave to students at Kenyon College in 2005, entitled “This is Water: Thoughts delivered on a Significant Occasion about Living a Compassionate Life.” Two fish meet an older fish swimming in the opposite direction. “Morning boys!” says the older fish, “How’s the water?” The two younger fish swim on, then one turns to the other and asks “What the hell is water?”

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Consumer greed is making suckers of us all

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Water, for Wallace, is the ubiquitous cultural presumptions in which we are all immersed, so all-surrounding as to be invisible. They are the beliefs that we all take for granted, that shape and sustain us. But the purpose of a good liberal arts education, Wallace maintains, is that throughout the boring everydayness of queueing at the supermarket checkout or whatever dulling routine our jobs lead us into, whatever the water in which we swim, it gives us the intellectual tools to take a step back and choose what to make of our circumstances.

“You get to decide what you worship” is how he puts it. “Because … in the day-to-day trenches of adult life there is actually no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship.” And a good reason for worshipping some sort of god is that “pretty much anything else you worship will eat you alive”.

What follows is like a preacher on fire:

“If you worship money and things, if they are where you tap real meaning in life, then you will never have enough. Worship your body and beauty and sexual allure and you will always feel ugly. And when time and age start showing, you will die a million deaths before they finally grieve you… Worship power, you will end up weak and afraid, and you will need ever more power over others to numb you to your own fear. Worship your intellect, you will always end up feeling stupid, a fraud.”

I was rocked by this address. “The insidious thing about these forms of worship is not that they’re evil or sinful, it’s that they’re unconscious. They are default settings.”

David Foster Wallace was himself a student during the high point of critical theory and post-modern philosophy, a cultural moment that emphasised the need for irony and a kind of self-referential knowingness that looked with suspicion, derision even, at all attempts at moral seriousness. Wallace, though, sought a return to what has come to be called ‘the new sincerity’, an attempt to recapture the sort of “passion, conviction and engagement with deep moral issues that we – here, today – cannot, or do not, permit ourselves”. The sort of moral seriousness that Wallace admired in a writer like Dostoyevsky.

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By Polly Mackenzie

Wallace saw his own culture as being trapped in a sort of feedback loop of knowing nods and winks, like one of those Ferris Bueller asides, when he breaks the fourth wall, looks straight into the camera and (apparently) wryly comments directly to those watching the film at home. In such a world, nothing is real, nothing is solid. Everything is exposed as sort of fiction, lacking true bottom. Those who pretend moral sincerity here become the butt of the joke, the rightly object of parody. Sincerity becomes the object of scorn. A laughable credulity.

In such a culture, we all have to pretend our utterances are tongue-in-cheek, even when we are trying to say something important, even when we are crying for help. For Wallace, “irony and ridicule … are agents of great despair and stasis in US culture.”

Irony, for Wallace, does have an important emergency function; it undermines the hypocrisy of authority. It is a shock tactic but it is not basis for culture as such. Because irony is “singularly unuseful when it comes to constructing anything to replace the hypocrisies it debunks”.

Here is the core of Wallace’s assessment of his cultural predicament:

“Even gifted ironists work best in sound-bites. I find them sort-of wickedly fun to listen to at parties, but … as for actually driving cross country with a gifted ironist or sitting through a 300-page novel full of nothing but trendy sardonic exhaustion, one ends up feeling not only empty, but also … oppressed.”

The ironist is an expert at destruction, at undermining authority, but offers nothing to replace it. We deliberately smirk at ourselves when why try and say something important or venture weighty things, pretending that we only half mean it. Like Ferris Bueller, we too feel we have to wink at the camera.

Two days after Wallace hanged himself, Lehman Brothers went into administration, an event that became emblematic of the global financial crisis that was to come. Wallace had spent his whole literary career trying to revive a form of moral sincerity that he believed had been hollowed out of American culture by the toxic irony of continual mockery. And he defiantly sought to revive the single entendre of moral seriousness from within a culture dominated by the double entendre of not really meaning it. Because, in such an environment, moral values had struggled to survive.

Further reading

Insincere politicians are cheapening public debate

By Giles Fraser

When some people dared to speak of right and wrong, cultural sophisticates smirked knowingly and chuckled at their naivety. Post-modernism had all but cleared the stage of moral sincerity. Looking back, it seems little surprise that the greedy and the powerful of Wall Street were able to fill their boots.

Our moral consciousness had been sabotaged, and, too busy laughing, we hadn’t really noticed. “This is Water” now reads like a warning. The change in our moral environment had been so thorough, deep and all-pervasive as to be invisible. And millions paid the price as houses were repossessed, savings wiped out, and wages flatlined. Governments bailed out the banks with billions and instituted programmes of austerity for the poor. The joke was well and truly over.