It’s hard—strictly, it’s impossible—to tell. Wallace was deeply suspicious of the media infrastructure that was, when he died, still largely known as “the Net”—“I allow myself to Webulize only once a week now,” he once told a grad student—and he remarked to his wife, as they were moving computer equipment into their house, “thank God I wasn't raised in this era.” Having written his first big stories on a Smith Corona typewriter, Wallace disliked digital drafts and e-publishing in general. (“Digital=abstract=sterile, somehow,” he wrote to Don DeLillo in 2000.) He liked to write long-hand, usually with cheap Bics he nicknamed his “orgasm pens.” He took particular pleasure in the fact that his house in Indiana, the one recreated in The End of the Tour, had the elegantly atavistic address of “Rural Route 2.” He preferred to file his students’ work not on computers, but in a pink Care Bears folder.

And he insisted that Infinite Jest, for all its obsession with commercialized communication and connection, was not about the web. When Valerie Stivers asked Wallace why the novel didn't specifically mention “online services,” he replied that “to do a comprehensive picture of what the technology of that era would be like, would take 3,500 pages, number one.” And when the Chicago Tribune asked whether Infinite Jest was meant to reflect life in the Internet age, the author rejected the reading. “This is sort of what it's like to be alive,” Wallace insisted. And “you don't have to be on the Internet for life to feel this way.” (Another reading, however: “The book is not about electronic culture,” Sven Birkerts, writing in the magazine then known as The Atlantic Monthly, noted, “but it has internalized some of the decentering energies that computer technologies have released into our midst.”)

And yet who better than Wallace to comment on the crazy world that is springing up both on and around the web? Who better than Wallace to help us make sense of Google and Snapchat and the far-reaching sociological experiment that is being conduced under the auspices of the “selfie stick”? Not only, as Maud Newton noted in a 2011 essay, has his writing style—its flippancy and its formality and its word-invention and its run-on sentences and its aggression and its passivity and its indolence and its urgency and its Ironical Creation of Capitalized Categories and its philosophy and its whimsy—been dissolved into a generation of Internet writers; his philosophical preoccupations also lend themselves to the Internet as a medium. Wallace seemed to have had a kind of preternatural (savant-garde, he might have called it) appreciation of what the web would bring as it made its way from “invention” to “infrastructure.” As he told Lipsky in Although of Course You End Up Becoming Yourself, referencing the web-service-esque InterLace Grid from Infinite Jest,

… This idea that the Internet’s gonna become incredibly democratic? I mean, if you’ve spent any time on the Web, you know that it’s not gonna be, because that’s completely overwhelming. There are four trillion bits coming at you, 99 percent of them are shit, and it’s too much work to do triage to decide. So it’s very clearly, very soon there’s gonna be an economic niche opening up for gatekeepers. You know? Or, what do you call them, Wells, or various nexes. Not just of interest but of quality. And then things get real interesting. And we will beg for those things to be there. Because otherwise we’re gonna spend 95 percent of our time body-surfing through shit that every joker in his basement—who’s not a pro, like you were talking about last night. I tell you, there’s no single more interesting time to be alive on the planet Earth than in the next twenty years. It’s gonna be—you’re gonna get to watch all of human history played out again real quickly.

What Wallace didn’t say, but what may well prove true, is that the overload he’s describing may come to apply to people as well as information. The Internet is composed, Soylent Green-style, of people—formerly atomized humans who, through their updates and posts and curiosities and contributions and selfies, are transforming themselves into media. We are just now figuring out what that might mean when it comes to the interplay of commercialism and human connection—the relationship that preoccupied Wallace in his writing. And authors, from Jonathan Franzen to Margaret Atwood to Joyce Carol Oates, are doing that figuring, too. As Meghan Tifft put it recently, discussing the demands on the writer to be introverted and extroverted at the same time, the writer is expected to engage in a “variety show of readings, interviews, conferences, and Q&As”—not just as a way of finding commercial viability, but as “a way of talking back, creating and sustaining a community around writing that matters.”