There’s a certain irony in making a feature film about David Foster Wallace: funneling the most voluminous of writers, he of the endnotes with their own gravitational pull, into a work of entertainment. The market, of course, is primed for a multiplex-filling movie. DFW’s fans have already consumed every available DFW product—not just his terrific short stories, or his 900-plus page dystopian novel on TV, tennis, and addiction, Infinite Jest; but also his critical essays, his Kenyon College commencement address, and his gonzo forays into reporting and travel writing. For the completist, there are also his interviews with Rolling Stone journalist David Lipsky from the Infinite Jest book tour of 1996—which have now been adapted as The End of the Tour, with Jason Segel playing DFW. But what emerges from those interviews and Wallace’s critical essays is his deep aversion to entertainment.

 “I think that if there is a sort of sadness for people under 45, it has something to do with pleasure, and achievement, and entertainment—like a sort of emptiness at the heart of what they thought was going on,” says Segel as Wallace, in the trailer. For most of his career, Wallace suggested that art ought to be difficult, that pleasure is suspect, and that entertainment is compromised. Art, Wallace told Lipsky, is a sort of superfood that “requires you to work.” (Italics his.) Entertainment is candy whose “chief job is to make you so riveted by it that you can’t tear your eyes away, so the advertisers can advertise.”

It’s taken a decade or so for me to wean myself off DFW and his ideas about entertainment. In fact, for a long time, his anti-entertainment campaign wasn’t always clear. For those who read them in real time, Wallace’s critical pieces were prescient responses to the enthusiasms and obsessions of the time—David Lynch, Mark Leyner, and Image-Fiction. (They appeared in niche publications such as The Review of Contemporary Fiction and Premiere.) For most of the rest of us—who read the essays when they appeared later in collections like A Supposedly Fun Thing I’ll Never Do Again—they meted out smaller doses of the idiosyncratic voice behind Infinite Jest. That voice hadn’t exactly been deployed on behalf of a generation, but it seemed to be the private discovery of droves of us, who were overeducated, steeped in pop culture, and unable to quiet our minds. “He’d done a thing that was casual and gigantic,” Lipsky wrote, “he’d captured everybody’s brain voice.”

By the time many of us got around to reading Wallace’s early critical essays, they were already period pieces—artifacts of the anti-corporate 90s, when it would’ve seemed necessary to decry the negative effects of television or bring down Brett Easton Ellis’s cohort. Nevertheless, after Infinite Jest, we were prepared to consume whatever variety and quantity of DFW we could. The subject matter hardly mattered. We read Wallace for his mash-ups of the academic and colloquial; footnotes that plunged the reader into fine-print; and the sort of sense of humor that breaks into an essay, on its twenty-ninth page, with the heading: “I do have a thesis.” We read Wallace because he was a lot of fun—even when he was warning us about the dangers of having too much fun. 

“E Unibus Pluram: Television and U.S. Fiction” is the most ambitious of his critical essays—the one that advanced a worldview and powered his most memorable fiction: Infinite Jest and short stories like “My Appearance” and “The Depressed Person.” Wallace began his tour de force by pointing out that fiction writers, anti-social by nature, constitute an ideal audience for television: they can observe others from the comfort of their own living rooms. (Wallace wrote at a time when people watched TV in living rooms.) He went on to diagnose how a particular strain of rebellious irony—which postwar American novelists had weaponized and leveled at various forms of authority—had come to be appropriated by media personalities and corporations. Pepsi and Isuzu, for example, had learned how to mock the oily salesmanship to which TV audiences, increasingly savvy and cynical, had grown impervious. Hip knowingness had saturated US culture. Irony, once a potent mode of critique, was impotent: deadpan on arrival.

Wallace then shifted his focus to show how postmodern writers like Leyner had internalized this defunct posture, resulting in “wonderful and oddly hollow” postmodern prose: “there’s a bar on the highway which caters almost exclusively to authority figures and the only drink it serves is lite beer and the only food it serves is surf and turf and the place is filled with cops and state troopers and gym teachers …”. He ended the essay with a prediction—and potential cure. “The next real literary ‘rebels’ in this country,” he wrote:

might well emerge as some weird bunch of anti-rebels, born oglers who dare somehow to back away from ironic watching, who have the childish gall actually to endorse and instantiate single-entendre principles. Who treat of plain old untrendy human troubles and emotions in U.S. life with reverence and conviction.

It’s a rousing passage, and it spawned the likes of Dave Eggers, The Believer, and other aggressively wide-eyed, cynicism-free phenomena. But then the essay is such a remarkable performance it’s easy to miss Wallace’s moralistic tendency to treat television as a social ill. Entertainment, he suggests in a later piece on Kafka, serves up escapism and reassurance—concepts Wallace seems to think are self-evidently bad. Wallace would most acutely dramatize the terrible dangers of entertainment in Infinite Jest, which posits a video so captivating it renders its audience immobile. Unable to care for themselves, the transfixed viewers eventually expire.

Was Wallace projecting an anxiety about his own vulnerability to entertainment onto the rest of us? He certainly recognized the pleasures of television and, more generally, entertainment. In an early interview, he confesses to consuming a “daily megadose of TV” and worries about his own tendency to want to entertain others. In a foreshadowing of the fatal video in Infinite Jest, he declares,

I think it’s impossible to spend that many slack-jawed, spittle-chinned, formative hours in front of commercial art without internalizing the idea that one of the main goals of art is simply to “entertain,” give people sheer pleasure. Except to what end, this pleasure-giving? Because, of course, TV’s “real” agenda is to be “liked,” because if you like what you’re seeing, you’ll stay tuned. ... And sometimes when I look at my own stuff I feel like I absorbed too much of this raison. I’ll catch myself thinking up gags or trying formal stunt-pilotry and see that none of this stuff is really in the service of the story itself; it’s serving the rather darker purpose of communicating to the reader “Hey! Look at me! Have a look at what a good writer I am! Like me!”

But Wallace’s anti-entertainment ideas have become so influential precisely because he wrote about them in an entertaining way—and The End of the Tour will, undoubtedly, be entertaining and spread his views ever more widely.

Not too long ago, while taking part in a panel on criticism, I pointed out that poetry was too often regarded as a source of nutrients rather than pleasure. A young woman in the audience took issue and with admirable sincerity alerted me to the dangers of entertainment. She was wielding, naturally, Wallace’s essay on television—as clunky a weapon as a cathode ray tube. Why would anyone read the doom-laden Wallace on television now, in the medium’s Golden Age? Only later did it occur to me that Wallace sticks with people—especially young people—in part because he’s addictive to read. Bad for you in bulk, but so much fun from sentence to sentence.