Early in James Ponsoldt’s small but oddly luminous The End of the Tour (in limited release 3 December), writer David Foster Wallace (Jason Segel) is hypothesising about his work and world view to a Rolling Stone journalist as they drive through the snow-covered Illinois countryside. It’s 1996, and Wallace’s Infinite Jest, a hyper-dense 1000-page ode to (and baroque enactment of) bewildered alienation in a postmodern, information-saturated world, has just burst upon the literary scene. “If the book is about anything,” says Wallace, “it’s about the question of ‘Why?’ Why am I watching all this shit? It’s just that it’s not about the shit – it’s about me.”

The journalist, David Lipsky (Jesse Eisenberg), listens, pensive. A writer with a couple of far-less-successful books than Infinite Jest under his belt, he’s carrying his own baggage about this new boy wonder. In one of the film’s opening scenes we see Lipsky reading from his new novel, The Art Fair, to a tiny crowd in a bookshop. Soon after – with that intense mix of jealousy and disdain some writers reserve for other writers – he’s reading Walter Kirn’s glowing New York magazine appraisal of Infinite Jest as “colossally disruptive” and “spectacularly good”. “‘Next year’s book awards have been decided,’” quotes Lipsky from the review, to his girlfriend Sarah (Anna Chlumsky). “Can you believe this?” (“He wants something better than he has,” Lipsky will write, years later, remembering the David Foster Wallace he got to know in 1996. “I want precisely what he has already.”)

“What if it actually is that good?” says Sarah. “You might just have to read it.” He does so. We see him still in the early pages. “Shit,” he murmurs. In the single exhalation you see both the admiration and the sinking heart.

In that car in snowy Illinois, Wallace continues ruminating. “We’re watching the best, most sophisticated electronic equipment money can buy. Why do we feel so empty, and unhappy?”

“Right,” agrees Lipsky. “It’s kind of like Hamlet, except with channel surfing.”

Lipsky trailed Wallace around for five days – at Wallace’s home in Illinois, in St Paul, Minnesota, for the final stop of the Infinite Jest book tour, and back to Illinois. As it turned out, the Rolling Stone article was never published. But 12 years later, after Wallace committed suicide in 2008, Lipsky dug up the old tapes, and in 2010 he published Although Of Course You End Up Becoming Yourself: A road trip with David Foster Wallace. The book – on which this film is based – is largely a transcript of those five days of interviews from 1996, with some essays and notes adding context and clarification.

“An act of base profiteering by an opportunistic half-wit,” wrote an Amazon reviewer of Lipsky’s book. “A movie that cashes in on a book that cashes in on another book that most people haven’t read but have heard is cool/important,” wrote a commentator on an End of the Tour IMDB thread. “What’s not to love?”

There are things to love. Screenwriter Donald Margulies, better known as a Pulitzer Prize–winning playwright, wrangled the raw material into a simple three-act structure. In Illinois, the two writers circle each other. Wallace seems aloof, evasive. The film becomes a road trip, of sorts. It’s like Sal Paradise and Dean Moriarty’s, only Wallace and Lipsky wolf down junk food and Diet Pepsi rather than benzedrine, and the pace of their thinking is a little more stately than that of On the Road. A kind of friendship begins to develop; so, too, do moments of conflict. We flinch at Lipsky’s prickliness. We see Wallace’s free association in action, his constant overthinking, his far-ranging intelligence, and the deep reservoir of sadness beneath his disarming sincerity.

It’s certainly a wordy journey, and if you’re not at least vaguely interested in the subject matter, it may not be gripping. But the words are Wallace’s, and the man had a way with them. Some find his words – in Infinite Jest, in particular – overwrought, too rich a banquet for easy digestion. But Lipsky’s book, and Margulies’ script, and Ponsoldt’s film give us something else. Wallace’s rambling monologues feel alive because they are unformed and off-the-cuff, haunting because in them we detect traces of the depression that would later take him under, and insightful because – for all his fumbling through his thoughts – he was nothing if not wise.

Wallace was fragile, too, and paranoid about the expectation that the newly lauded writer must participate in the propagation of his own fame. To Wallace, Lipsky is at first a double-headed monster: he’s from Rolling Stone, which will make Wallace a rock star whether he wants it or not, yet he’s also part of the New York literary elite, with its “enormous hiss of egos in various stages of inflation and deflation”.

What’s the piece even about, Wallace asks Lipsky, as if there might be an acceptable answer. It’s about what it’s like to be the most talked-about writer in the country, says Lipsky. “You’re going to go back to New York,” Wallace says, “and sit at your desk and shape this thing however you want. To me it’s just extremely disturbing.”

Wallace pushes and pulls. “I don’t even know if I like you yet. And I’m so nervous about whether you like me.” As for Lipsky, we get the feeling he doesn’t so much care about being liked; it’s more about being acknowledged – as a fellow writer. When Lipsky brings up the subject of his own books, Wallace picks up on it. “You’re, like, a nervous guy, huh?” he asks, with gentle amusement. “No, no, no, I’m OK,” says Lipsky, and then throws it back: “How are you?”

It’s his neediness that opens the door, a crack. “I’m terrified,” says Wallace.

That terror was not just about whether Lipsky, or indeed the whole world, would like him. It was about losing the private him to the him-in-relation-to-fame. “I don’t mind appearing in Rolling Stone. But I don’t want to appear in Rolling Stone as someone who wants to be in Rolling Stone.” Elsewhere, they joke about whether Wallace should trade sexually off his success. (“What I want is not to have to take any action. Like, I don’t want to have to say, ‘Do you want to come back to the hotel?’ I want them to say, ‘I am coming back to your hotel. Where is your hotel?’”) He’d feel lonely if he did it, though, he says, because in such a circumstance it would be all about the fame.

Lipsky, for whom literary groupies seem highly unlikely just now, is not so sure. “If they’re responding to your work,” he says, “and your work is really personal, then reading you is another way of meeting you.”

Wallace said that Infinite Jest was a book about loneliness. The End of the Tour shows him being profoundly alone – adrift in the very pop-cultural vacuity that his works attempted to pierce. He knew, too, that the more “connected” we all became, the more collective the loneliness would be. “The technology is just going to get better and better,” he tells Lipsky, “and it’s just going to get easier and easier, and more convenient, to sit alone – with images on a screen, given to us by people who do not love us, but want our money.” Coming from that long-gone frontier of dial-up internet, the throwaway thought seems prophetic.

Eisenberg and Segel give nuanced and complementary performances: the nervous little whippet and the world-weary basset hound. It’s not a tale about Wallace in which Lipsky figures. Rather, it’s about Lipsky’s processing of the “best conversation” he ever had, and his five-day journey from wariness to gratitude.

For a time, he’s suspicious of Wallace’s apparent vulnerability and openness. Surely that’s a façade, a superiority complex all its own. How could you write a book so brilliant and not be superior? “You feel you’re smarter than other people,” Lipsky tells him. “You act like you’re in the kids’ softball game but you’re holding back your power hitting to try and make it more competitive for the little ones.”

“I don’t think writers are smarter than other people,” counters Wallace. “I think they may be more compelling in their stupidity. Or in their confusion.”