Infinite Jest is frequently attention-repellent. David Foster Wallace’s brick-sized novel is physically challenging, an 800g book that forces you to flick back and forth to the errata. This is not optional. Major plot points hinge on throwaway glosses. 

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 the internet.

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”. 

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.

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.

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.

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