illustration by Brianna Ashby

“David had a caffeine social gift: He was charmingly, vividly, overwhelmingly awake – he acted on other people like a slug of coffee – so they’re the five most sleepless days I every spent with anyone.”
—David Lipsky

Sitting in a packed to capacity theater last weekend, waiting to see the Seattle premiere of The End of the Tour with a thousand other David Foster Wallace acolytes, the underlying hum of anticipation a palpable, tangible thing amidst a hundred other things—the smell of overly-buttered popcorn and a dozen previous screenings from the festival, the slightly sweaty feel of a surprisingly warm May evening in a city known best for its rain, people sitting just a bit too close to one another, trying to avoid arms, elbows, legs—I felt sad. And by the end of the film, despite the fact that director James Ponsoldt and star Jason Segel absolutely pull off, in every important way, the near impossible task of getting DFW right on the screen, the sadness felt almost unbearable. I wasn’t alone in this; many around me were wiping their eyes as Tindersticks’ cover of Pavement’s “Here” played over the closing credits. Some weeped openly. It was an odd experience, given that the film doesn’t end in any kind of conventionally “sad” manner, nor is the main thrust of the film all that narratively sad anyway, provided you remove its present day bookends, which take place in the days following Wallace’s suicide in 2008. In fact, The End of the Tour is actually an extremely lively, funny, and engaging film.

But there’s a great melancholy at the heart of it too, undeniably so. It’s what remains when the film fades to black. As best I can tell, this sadness has something to do with loneliness, both ours and Wallace’s, and how difficult it is just to be a human being trying to connect with other human beings. At his best, Wallace wrote about how impossible it was to truly know or connect with others in any kind of important or authentic way, despite our wired-in yearning to do so; how solipsism and anxiety and an addiction to the pleasures and artifice of modern American culture—with its fragmentary focus, narcissistic impulses, and worship of soul-numbing devices and mindless entertainments—had rendered us obscenely disconnected from one another, and ourselves, and fundamentally unable to connect with the truly important things that might actually save or sustain us. Yet he also realized how almost impossibly difficult it was to step outside of all of that seductive American noise, and found himself just as seduced as any of us (if not more so) by this cultural barrage of base, empty, momentary pleasures. It was a dilemma he returned to time and again, in both his fiction and his non-fiction: how to connect and empathize with others, how to lead a decent life that made any kind of sense or tasted real in the face of endless distractions and false gods. If he ever was anything like “the voice of a generation”, it was largely because he was able to diagnose, in painstaking detail (complete with footnotes), the central maladies and malaise of our modern times and the deep loneliness at its core—a loneliness we had hoped education or income or intoxication or entertainment might cure, only to realize that these things were just more empty calories, serving to dig the hole ever deeper. Still, as he says in the film, he has no simple cure to offer for any of this; he can shine a light on the path we’re navigating, and highlight its steep costs, but he has no real idea how we ever get off of it. And he worries it just might be terminal.


Wallace’s diagnosis, of course, wasn’t wrong. In fact, it holds every bit as true today as it did back in 1996—and then some. (Some of the great sadness around Wallace no longer being with us is that we’ll never get to know what he would have made of Twitter or Tinder or Candy Crush, of an entire culture tethered to their small-screened masters.) We have an entire world at our fingertips—nearly any fact, song, friend, game or entertainment available to us instantly and at all times—but we seem lonelier than ever.

In my work as a therapist over the past ten years, conversing intimately with people in one of the few remaining sacred spaces smartphones haven’t yet invaded, I’ve seen a good deal of this loneliness right up close. On some fundamental level, most of the people I work with—despite all of their intelligence, achievements, and success—struggle with loneliness. This loneliness rarely stems from physical isolation or a lack of relationships, but rather from a much deeper place, an unscratchable existential itch that seems to have something to do with not feeling much of an actual connection with others or the world around them, not belonging to any larger network of community or meaning, not being seen or accepted in the ways in which they experience themselves.

It’s not that loneliness hasn’t always been with us—to my mind, it’s at the very root of the human condition, a substratal struggle one is always wrestling with or trying to avoid—it’s just that it’s more apparent now than ever, when so much of what we thought would make us happy has come to pass, and hasn’t. (Or, as Louis CK famously said a few years ago, “everything’s amazing and nobody’s happy!”) It’s as if it took us several centuries of technological growth—and a couple hundred years of chasing after the American Dream—to realize, finally, that these things will never make us happy. That “happiness” itself is just one more thing someone somewhere is trying to sell to you—and that chasing after it is only making you feel a whole lot worse.

Having learned this the hard way in his 20s, Wallace knew it firsthand, and spent the rest of his life trying to communicate it to others. At one point in The End of the Tour, during a casual discussion about the seductive, hypnotic allure of television and the internet, he suddenly gets crystal-clear intense:

“…the technology is just gonna get better and better and better. And it’s gonna get easier and easier, and more and more convenient, and more and more pleasurable, to be alone with images on a screen, give to us by people who do not love us but want our money. Which is all right, in low doses. But if that’s the basic main staple of your diet, you’re gonna die. In a meaningful way, you’re going to die.”


Like the best of David Foster Wallace’s writing, The End of the Tour is a film both sparkling with the alacrity of life and rife with dilemmas and double binds. Based on writer David Lipsky’s Although Of Course You End Becoming Yourself—which started life as an attempt at profiling Wallace for Rolling Stone in 1996 (a few short months after Infinite Jest was released) only to be aborted and then later resurrected, after Wallace’s death, as a full-length book chronicling their time together—the essential dynamic and dilemma at the heart of the film is the relationship between Lipsky and Wallace, interviewer and interviewee, journalist and subject. But of course, it’s never that simple: Lipsky, a published but not well-known fiction writer himself, approaches Wallace with a mixture of jealousy, curiosity and awe. For his part, Wallace greets Lipsky, who travels from New York to Wallace’s home in Indiana to spend time with him, with cautious ambivalence—a hesitant, distrustful apprehension at what the journalist might make of him. (This approach wasn’t unique to just Lipsky, it was also largely Wallace’s default setting—despite his prodigious talents and gifts, he was often insecure and hypervigilant about how he was being perceived.)

“It’s a very fine line. I don’t mind appearing in Rolling Stone, but I don’t want to appear in Rolling Stone as somebody who wants to be in Rolling Stone.”

These early scenes in the film, as Lipsky and Wallace get to know each other, are pitched somewhere between a chess match and a dance. On one hand it’s a very familiar male ritual, a territorial sniffing out and sizing up, establishing the contours of control through coded conversation. The two have a good deal in common—highly educated, intelligent, articulate, sensitive, self-conscious white male writers in their early 30s—and both of them, at times, trade on this overlap to endear themselves to the other for self-serving purposes.

On the other hand though, as Wallace points out more than once, they are approaching each other with vastly different agendas. Lipsky wants a good piece (and also, more transparently as the film goes on, some of what Wallace has—fame, adulation, appreciation, a readership) and can become subtly aggressive, armed with endless questions and a tape recorder always firmly in hand. Wallace, however, is primarily concerned with both being liked and managing how he’s being perceived, acutely aware of how his newfound literary fame positions him as an easy target for others’ scorn or displacement. He’s hyper-aware and sensitive, trying to figure out what Lipsky wants and how to give it to him, either to connect and assuage his own loneliness, or to get a fair shake in the piece Lipsky is writing. Therein lies the chess match, the beginnings of the dance—and it’s every bit as entertaining as any good romantic comedy.


“When I think of this trip, I see David and me in the front seat of the car. It’s nighttime. It smells like chewing tobacco, soda, and smoke…we seem not to be moving at all, and the conversation is the best one I’ve ever had.”
—David Lipsky

As much as it’s a film about Wallace, The End of the Tour is also a road film, following DFW and Lipsky across time and space, all the untold miles logged between Indiana and Chicago and Minneapolis and New York, in the span of just five days. And like any good road movie, it invites you along on the journey. We spend a lot of time in the car with Wallace and Lipsky, but never, not once, does this lend the film any sense of claustrophobia or ennui. If anything, The End of the Tour is much more akin to something like Linklater’s Before films, in which not a whole lot happens but where, through conversation and suggestion, an entire world is revealed.

We get a real felt sense—and much credit here to director Ponsoldt, screenwriter Donald Margulies, and stars Jason Segel and Jesse Eisenberg for this—of both Wallace and Lipsky as people rather than mere characters in service of a plot. At times we’re in Wallace’s headspace, observing and absorbing the world through his unique and overwhelming consciousness; at other moments, we identify with Lipsky, anxiously noticing and navigating the blurring boundaries between subject and interviewer, wandering around in Wallace’s buzzy wake, a kind of Almost Famous sense of being right up close to something so rock star magical and yet trying to stay diligent and focused on the task at end. (And, as in that film,Rolling Stone is once again footing the bill.)

One of the more remarkable things about the film—and its pleasures are many—is that most of its best lines aren’t lines, that they were actually spoken, verbatim. As impressive and charming as Wallace’s nonfiction essays often were, he was just as brilliant and loquacious in conversation, speaking in a kind of prose rhythm every bit as engaging as the stuff he ever got on the page (here’s an audio archive of his interviews, by way of example). And it’s in these moments, seeing the world through Wallace’s eyes, that the film becomes most alive, the conversations between Lipsky and Wallace allowing us, by proxy, to feel smarter, more tuned in to the world around us, more human. Listening to him expound on everything from the purpose of art (“I have this unbelievably like five-year-old’s belief that art is just absolutely magic, and that good art can do things that nothing else in the solar system can do”) to his fondness for Alanis Morrisette (“If by some paradox this whole fuss could get me some kind of even just like five-minute cup of tea with her, that would be more than reward enough. Although, of course, I’d never do it. I’d be too terrified”) is immensely rewarding, making us want to stay in this world, and Wallace’s orbit, for as long as possible.

Of course, none of this really works onscreen without Segel’s astounding, pitch-perfect performance. The degree of difficulty here, really, is off the charts; there are a hundred different ways Segel could have failed, miserably, and taken the entire film down with him. That he doesn’t, that he actually captures Wallace—the lumbering physicality and Midwestern drawl, the recursive self-consciousness and subtle internal machinations, the various shades of Wallace’s persona and affectations—without making him a caricature or offering up an SNL impression of him, is remarkable. Nothing, really, in Segel’s past performances (with the possible exception of his early work on Freaks and Geeks) spoke to the possibility of this type of nuanced, lived-in performance.

Eisenberg is good too, in a far less showy but fine-line difficult role. He inhabits Lipsky with a palpable neurotic intensity that never loses our sympathy, despite the many different hats he has to wear with Wallace throughout the film (journalist, confidant, interrogator, peer, counselor, friend). He’s our stand-in, of course, and you sense that he gets that. We all wish we had Wallace’s talent and gifts, but at the end of the day we’re a whole lot more like Lipsky, the guy following him around and trying to keep up with his genius, and Eisenberg mostly makes this a palatable alternative.


As both a writer and a person, David Foster Wallace seemed to orbit endlessly around the idea of double binds—unresolvable personal, cosmological, or moral dilemmas that fascinated him on an intellectual level even as they wore away at him on an emotional one, eating away at the fragile, tenuous sense of self he constructed to meet the world with. He was, by many accounts, the smartest person in any room he entered—as much as he prided himself on being a “regular guy”—but with that ferocious intellect came an often crippling self-consciousness:

Am I a good person? Deep down, do I even really want to be a good person, or do I only want to seem like a good person so that people (including myself) will approve of me? Is there a difference? How do I ever actually know whether I’m bullshitting myself, morally speaking?

Aware, curious, and fiercely observant of the world both inside and around him, he possessed an uncanny sponge-like ability to soak it all up on an almost cellular level, digest it, and give it back to us in ways we could understand. He showed us, in ways we couldn’t always articulate, the sheer magic of things but also the vast enormity of all we’re up against; how vitally important and necessary the struggle was, and how we might best be able to countenance it.

It’s got something to do with love. With having the discipline to talk out of the part of yourself that can love instead of the part that just wants to be loved.

Watching The End of the Tour, Wallace is with us once again, if only for a moment. His charm and humor, his curiosity and contradictions, his firecracker intellect and bone-deep loneliness, they’re all right up there on the big screen, flickering. When it’s over—when it’s time for Lipsky (and by extension, us) to leave him—we begin to feel the sadness of his absence all over again. It’s not 1996 anymore, and can’t ever be again. Wallace’s star, just beginning to shine at the time Lipsky first encountered him, burned out nearly seven years ago now. The loss feels immeasurable. Still, this moment in time existed, too, and somebody captured it, faithfully and lovingly. It will never be enough, but it is something.

And that’s not a dilemma, it’s a gift.