Taking Wallace at his word about his desire for redemptive stories finally turns our attention away from what, twenty years later, may be most special about it: its experimental quality. “Infinite Jest” is a novel about the narcotic power of language—a power so overwhelming that Wallace has to shred narrative into tiny strips to keep it under control. Stories nest within stories; experiences are fragmented and regroup; there are bad jokes and goofy science fiction (giant feral hamsters are marauding through Vermont). The result resonates, as the critic Sven Birkerts savvily noted at the time of publication, with the vibe of the Internet. So where's the problem? Isn't writing about the Internet writing about what it's like to be a “fucking human being,” too? Yes, but not really in the way Wallace meant it. What he understood—and what we understand—as his plan was a revival of a kind of novel that had gone out of fashion, one in which the writer hugs his characters to himself, closing the ironic distance that writers like Salinger had carved into fiction's bedrock. Wallace's goal, as he wrote to Birkerts, daringly, in 1993, was “a kind of contemporary Jamesian melodrama, real edge-of-sentimentality stuff.”

Did he think he had succeeded? Perhaps not. In the letter to Birkerts, the book nearly done, Wallace compares the novel to a story he had published several years earlier, “Little Expressionless Animals,” and worries that he hasn’t gotten past that earlier work’s limitations: “I find it buried—like parts of ‘L.E.A.’—in Po-Mo formalities, the sort of manic patina over emotional catatonia that seems to inflict the very culture the novel’s supposed to be about.” He added, “I have never felt so much a failure.” I'd caution against reading too much into this despair, though. The more I reread Wallace's letters, the more skeptical I get of their overt opinions. Wallace was exquisitely aware of social relations; his letters are a series of stances. Of course, despite his protests to McCaffery, he was a good interview—indeed, a great one. Here, similarly, I think he is ritually offering his nape to the critic-wolf Birkerts, encouraging an important reader to approach him with compassion. Besides, he wrote the note while stranded at O'Hare Airport, a situation that could make any writer despair of his ability to give CPR to what's human.

“Infinite Jest” was published in February, 1996, and critics were split between enthusiasm and doubt, often in the same review. Nearly all, though, praised its prodigious energy. This was new stuff, and it took them a while to catch up. What really propelled “Infinite Jest” into the culture were not the critics but a cohort of readers, many of them in their twenties. The first wave of enthusiasts were bewitched by the book’s pyrotechnics—“It was DFW's lexical genius; no one had really seen it since Pynchon,” Matt Bucher, who runs the Wallace-l Listserv, remembers—more than Wallace's ideas about redemption. But soon a different kind of reader emerged to spread the word, the intense celebrants who carried it like a totem, aided in their interpretation of a crafty, complex story by Wallace's promise of deliverance. “Infinite Jest” owes its diffusion through the culture most of all to this group.

Here's where it gets tricky. Nothing Wallace would publish after “Infinite Jest” would hit such a chord again, though he would go on to put out three other works of fiction. Two came out during his lifetime: the story collections “Brief Interviews with Hideous Men” and “Oblivion.” They are very different books from each other, and most of all from “Infinite Jest.” At the core of “Brief Interviews” is a series of Q. & A.'s between an unnamed female interrogator and a number of distorted or impacted men. Responses are terse; anger or anxiety tamp down utterances. “Oblivion” is almost the reverse in style: a maximalist, vocabulary-expanding set of formally complex stories circling around anomie like it was a black hole. Both books have fans, but I think it's safe to say that no twenty-year-old will ever stick either of them in his or her backpack alongside “Infinite Jest” when they go trekking in Nepal. In the end, neither found the sustained audience that “Infinite Jest” did, nor the critical response. And much of the resistance can be traced to the mid-nineties, when Wallace annunciated a glorious and exciting new philosophy of writing as clearly as if he had stuck it on a billboard on Sunset. Critics expected him to pursue it. Faced with “Brief Interviews,” in 1999, Michiko Kakutani, the New York Times reviewer, accused Wallace of writing an “airless, tedious” book, and specifically spoke of her disappointment that it did not fulfill the stated goals of “E Unibus Pluram” to breathe new life into the “deep moral issues that distinguished the work of the great 19th-century writers.” Wyatt Mason, one of Wallace's most incisive readers, finally threw up his hands at “Oblivion,” in 2004, in the London Review of Books: “Wallace has the right to write a great book that no one can read except people like him. I flatter myself to think that I am one of them, but I haven’t any idea how to convince you that you should be, too; nor, clearly, does Wallace.” Mason registered a gentle request for something “more generous” next time.

How did Wallace feel being hit on the head by his own manifesto? We don't really know. He never published an essay to refute it, nor gave an interview that served as a corrective. I've never seen a letter where he protested, “That was me then; this is me now.” The novel that he worked on from the time he finished “Infinite Jest,” “The Pale King”—published, posthumously, in 2011—complicates the story, potentially. In it, Wallace tries to make the case that boredom is the only refuge from what he called elsewhere the “Total Noise” of modern society. Parts of the novel are prescriptive, guides to how to live a meaningful life, not unlike parts of “Infinite Jest.” But Wallace never finished the book—indeed, couldn't figure out how to weight its different ambitions. There is, also, an intellectuality to the impulse, absent from Wallace's cheerleading for Gately. That's in part because Wallace, it's fair to say, if one thinks about the life and the work as two expressions of the same impulse (as biographers tend to do), continued to aspire to be Gately—read his famous Kenyon College address from 2005—even if he didn't really want to invent him on paper a second time. And, at least occasionally, he expressed pride in his post-“Infinite Jest” stories, telling the novelist Mark Costello, for instance, that with “Oblivion” he had finally written a book that was free of tricks, gambits, and gags. “I looked straight into the camera,” he told his friend.

Still, I feel a sadness around all of this, a whiff of injustice. As we celebrate the twentieth anniversary of the book that remains Wallace's masterwork, out in a new edition with a foreword by Tom Bissell next week, I for one am now much more focussed on the fiction that lay ahead for him, especially the two story volumes. Alongside his first collection, “Girl with Curious Hair,” published in 1989, “Brief Interviews” and “Oblivion” cumulatively make the case for Wallace as one of the most interesting short-story writers of our time. It's hard to remember today just how weird “Brief Interviews” was when it was published, with its proposal to draw individuals entirely from their clinically clipped dialogue. And the various stories in “Oblivion,” superficially about insomnia or the tense tediousness of office life, actually are about the instability of experience. One story has a narrative that meanders from protagonist to protagonist and a climax that feels almost peevishly withheld; it lacks not only a single-entendre principle but a stable point of view. Does it matter if “Brief Interviews” seems to owe more to Gogol than Dostoyevsky and “Oblivion” more to Kafka—or maybe Nabokov? They make you wonder if trying to redeem us was the wrong goal for Wallace all along, or if, alternatively, he simply, having accomplished one thing, set his sights on the next. I don't know, but I hope that when 2019 and 2024 come around, we celebrate those books, too.