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.