The novelist David Foster Wallace predicted many features of the modern world—FaceTime, Netflix, Twitter, data-sickness—but it’s safe to say that even he never imagined anything like The End of the Tour, the new biopic starring Jason Segel as Wallace himself. The film recreates a five-day road trip Wallace took in 1996 with Rolling Stone scribe and struggling novelist David Lipsky (Jesse Eisenberg), right after the publication of his doorstop-masterwork Infinite Jest. It’s based on Although of Course You End Up Becoming Yourself, Lipsky’s record of their conversation, published two years after Wallace’s 2008 suicide.

Wallace was one of those authors who was intensely suspicious of fame and the potentially dehumanizing impact of having a public persona. He never went Full Hermit, like Thomas Pynchon or JD Salinger, but his interactions with the media were always self-conscious and uneasy. These concerns actually take up much of the text of Lipsky’s book. Wallace worries that he will get hooked on publicity, that Lipsky will portray him in an unflattering or incomplete light, that he will be made into a caricature. “I don’t want to turn this into a romantic, lurid, tormented-artist thing,” he says at one point.

That line didn’t make it into the film. And while you have to give the filmmakers credit for making a movie that is mostly a line-by-line recitation of Wallace’s own words, they did throw in a couple of extra details that help make the movie more… movie-like. (Spoiler alert, I guess, though almost all of these moments are in the trailer.) Like the subplot in which Lipsky hits on one of Wallace’s ex-girlfriends. Or Wallace’s Buddha-like advice as he urges Lipsky to knock it off: “Just be a good guy.” Or a full-on second-act blow-up, an inflated version of what was not necessarily even a disagreement in the book. Or Wallace’s words to the envious Lipsky: “I’m not so sure you want to be me.” Or the shot of Wallace dancing beatifically amongst strangers, bathed in golden sunlight. (Really!)

Although Of Course You End Up Becoming Jason Segel, I guess.

In Which We Get to the Point

I don’t mean to come down too hard on the film. It’s impossible to imagine that it was made out of anything but sincere affection for Wallace and his work. (If you’re trying to come up with a cynical cash grab, I wouldn’t suggest a My Dinner With Andre-like road movie about an experimental novelist.) Segel is likeable, as always, and he gives a performance of sensitivity and depth. But it leaves the audience to grapple with the contradictions inherent in turning Wallace into a movie character—and those contradictions speak profoundly to our lives and culture today.

Back when Wallace wrote Infinite Jest, not too many of us had to worry about the impact our public personae would have on our interior lives, simply because only a few of us had public personae. (Well, OK, we all have public personae, but you know what I mean.) But today that angst has been democratized—all of us aswirl in FOMO and filters, measuring our vacations in selfie-stick lengths. The distance between experiencing/thinking/feeling something and packaging it for public approval is consistently shrinking, as lovingly buffed Facebook updates give way to Periscope live feeds. We are all performers now, even of our most intimate moments. Back in the ’90s, this kind of thing was the domain of alienated grunge musicians. Now it’s so universal as to be a cliché. (Indeed, after I wrote this I discovered – somewhat to my dismay – that Jason Kottke made a similar observation when the Lipsky book came out.)

It was David Foster Wallace’s misfortune to feel the anxieties of the Internet Age before they fully arrived. That distance, between public face and private self, was one of Infinite Jest’s many themes. The very first scene involves a tennis prodigy interviewing for a college scholarship who is unable to control his outward appearance. (“I believe I appear neutral, maybe even pleasant, though I’ve been coached to err on the side of neutrality and not attempt what would feel to me like a pleasant expression or smile.”) This Cartesian split is pretty familiar literary ground; Hamlet, a play that Infinite Jest deliberately evokes in its title and many of its plot elements, covered it pretty well. But Wallace updates those concerns for the emerging digital age. At one point, he digresses into a fictional history of the rise and fall of the videophone; faced with the prospect of beaming their likenesses in real time to friends and loved ones, callers become vain and insecure, spurring them to wear increasingly attractive masks that bear less and less of a resemblance to their actual faces. That wasn’t a perfect prediction of how we use FaceTime, but it’s a pretty great metaphor for the imperfect fit between our digital social lives and our more complicated psychological and emotional ones.

But perhaps Wallace’s greatest prediction was his vision of a society held captive by artifice, preferring simulations of human relationships to the real thing. Wallace, an addictive TV viewer, was apparently disturbed by his own habits. “What has happened to us, that I’m now willing—and I do this too—that I’m willing to derive enormous amounts of my sense of community and awareness of other people, from television?” he asks Lipsky at one point in the book. “But I’m not willing to undergo the stress and awkwardness and potential shit of dealing with real people.” The inevitable response to this urge, in Wallace’s fiction, was The Entertainment, a film so compelling it killed viewers by rendering them powerless to do anything but watch it. That may have sounded a bit overheated at the time, but maybe less so today, when we have to establish strict rules to prevent ourselves from checking our smartphone during family dinner or while cruising down the highway.

For Wallace, the problem wasn’t technology per se, but our own self-immolating response to it, an inability to connect with other people, a fear of being alone with our thoughts, that channeled itself into obsessive consumption. “If the book’s about anything,” he tells Lipsky in the book and in the movie, “it’s about the question of why am I watching so much shit? It’s not about the shit; it’s about me.” He goes onto predict that whatever that force is, it’s going to leave us powerless in the face of ever-more-sophisticated escapist technology. “In 10 or 15 years, we’re gonna have virtual reality pornography,” he says in the book. (He was off by five or 10 years, but still, not bad.) “I don’t know about you, but I’m gonna have to leave the planet.”

Empathy Machines

For Wallace one solace was writing and reading, a consciousness-sharing technology that to his mind had never been improved upon. “We all suffer alone in the real world,” he famously told The Review of Contemporary Fiction. “True empathy’s impossible. But if a piece of fiction can allow us imaginatively to identify with a character’s pain, we might then also more easily conceive of others identifying with our own. This is nourishing, redemptive; we become less alone inside.”

There are a lot of reasons to be sad that David Foster Wallace is no longer with us. Personally, I would have loved to have heard his reaction to Chris Milk’s TED presentation. Milk, a digital artist, focused on how virtual reality could be used to create empathy. He concluded his talk by screening a VR video he had developed in partnership with the UN, a testimonial from a 12-year-old Syrian refugee living in Jordan. “You’re not watching her through a TV screen, you’re not watching through a window. You’re sitting there with her,” Milk said. “And because of that, you feel her humanity in a deeper way. You empathize with her in a deeper way.”

It didn’t strike me as bullshit. To the contrary, it suggested that these technologies, which we so often use to distract and dehumanize ourselves, can also be used to reconnect us with our humanity. I thought the same thing a few months later, when I read Sheryl Sandberg’s deeply moving Facebook post upon returning to work following her husband’s death. “Real empathy,” she wrote, “is sometimes not insisting that it will be OK but acknowledging that it is not.” Almost a million readers liked the post, and more than 70,000 commented on it, many of them to share their own experiences with grief. “I finished reading this—a post from someone I’ve never met—and yet felt such a connection that it left me shaken,” read one comment, from a woman who had lost her spouse five years earlier.

The future that Wallace predicted may have come to pass, with its virtual reality porn and near-constant performance anxiety. But it has also created the potential for deeper connections and empathy. If we feel alone, it is not at the hands of technology, but because of our own limitations and weaknesses and weirdness. “The technology’s gonna get better and better at doing what it does, which is seduce us into being incredibly dependent on it, so that advertisers can be more confident we will watch their advertisements,” Wallace tells Lipsky in the book. “And as a technology, it’s amoral. It doesn’t have a responsibility to care about us one whit more than it does. It’s got a job to do. The moral job is ours.”