“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?” – David Foster Wallace

The new tagline for the James Ponsoldt movie The End of the Tour is, “Imagine the greatest conversation you’ve ever had.” I initially took issue with this tagline. Ponsoldt’s film is based on a book arranged around a transcript of an unpublished interview that the writer David Lipsky did for Rolling Stone with David Foster Wallace at the end of Wallace’s king-making press tour for his novel Infinite Jest. It is not, in a literal sense, a conversation any of us will ever have, and therefore, could ever imagine. We will never be them, in that moment. The best conversation any of us have ever had wouldn’t be like that, so why imagine it in service of this movie? (Also, how can you imagine something that you already did?) Plus, some people are more interesting than other people, and those two are more interesting than me. I decided that the tagline should read, “Imagine the best conversation you will never have.”

But then I had a conversation with James Ponsoldt. Full disclosure: I’ve had a lot of conversations with James. I’ve known him for a long time, because when we were basically strangers, more than 10 years ago, just-graduated-college kids doing our jobs for the first time, we drove across the country together. The conversation on that road trip was indeed one of the best that I have ever had. And I suppose that trying to remember something important to you is, in a way, “imagining” it — you dream of what it meant more than you can actually recall what was said.

I have decided that I like the tagline.

Ponsoldt — whose previous films are Off the Black, Smashed and The Spectacular Now — loves superlatives. Everything with him is The Best Poem About God You Will Ever Read or The Most Amazing Piece of Trivia About Ronald Reagan Ever or The Most Incredible Roast Beef Sandwich You Will Find in Los Angeles With Some Exceptions If You Count French Dip Sandwiches Downtown. He is a person who values truth and sincerity in truthful and sincere ways while being a savvy navigator of Hollywood waters who worries a lot about making the right moral decisions. He has a lot of great conversations.

On a superficial level, The End of the Tour is a simple movie. Two guys take a road trip together in 1996. One of them is getting famous; the other is jealous of him. Both men want several things that they wish they didn’t. David Lipsky (Jesse Eisenberg) wants a good story, and also wants to be friends with David Foster Wallace (Jason Segel). Wallace wants the story to be good and wants to be understood, but Lipsky is viciously jealous of Wallace and hates himself for it. Wallace doesn’t want to care about how he comes across in the press, and he wants to be a good guy in spite of the temptations of fame. They both want the other one to like them, and they’re angry at themselves for caring about it. In any given exchange, there is so much going on between these two — so many ideas, tangents and references, so many power plays, so many sideways glances and hidden agendas and swoons of affection-mixed-with-resentment — that to pin down what each scene is “about” is impossible. Which is, in fact, what the best conversations you’ve ever had are like; whatever they are superficially about, they are actually about everything.

I’m interviewing you on a day when a big new announcement came out about yet another movie you’re involved in. And your upcoming movie The Circle was called in the trades the hottest package at Cannes. You are, by really any definition, “very successful.” Is your relationship to success changing? I think I am more aware of how much success is like, perception and a lot of hokum. [Laughs] “Success” is not as real, maybe, to the people who are supposedly successful? Those announcements just make good copy.

Oh, please. It’s nice to have options? I don’t know. It’s nice to work with people who you admire or maybe to have them want to work with you. I don’t know.

This is an uncomfortable line of questioning for you, because another key characteristic of who you are is No. 1 Most Enthusiastic Super Fan Of Everything. Yeah. I don’t relate to David Foster Wallace, I relate to David Lipsky. I’ve had far more experiences where I got to meet for five minutes someone who I really admired and found myself tongue-tied or saying stupid things and running away, embarrassed.

The reason I’m asking about success is that it’s such a huge theme of the movie. How do you define it; what does it mean to the people who have it vs. to the people who don’t — whatever “it” is? So, what, in your own experience, makes someone successful or not? How do they get that way? Oh, man. This is a Rorschach.

It’s a Rorschach test? It is a Rorschach test of where you find value. I can say, and this is not a considered answer, that the people who impress me the most are the people I know who professionally are able to make movies or TV shows they are really into when they want to and with integrity. And they are also able to have a family and to be very invested in the lives of their family. And they are also able to reply to emails quickly. I know that sounds silly, but do you know what I mean?

I totally know what you mean. Consistent correspondence is the hallmark of truly successful people. Well, it feels like there is a stability, a value system, a groundedness, a mental health — it just all works. That’s what blows me away the most — that the people I know who are the most “successful,” at least professionally, most of them actually are very, very prompt in getting back to you, which always kind of shames me. And it always reminds me, “Oh, yes, you should be a decent person first and foremost.”

Is this movie about success, for you? Endlessly about success. The end credit song is the Tindersticks covering “Here” by Pavement. The first line is, “I was dressed for success.” [Laughs] Yeah, I mean, it is about that. And it’s about ego, desire and self-worth and how we measure our own worth, and where we assign value and what gods we choose to worship. Measuring ourselves against other people. What it means to live a good and honest life. All those things. If you’re trying to live a mentally healthy and happy life, but your chief obsession is your career, there might be some other parts of your life suffering, you know? That’s not a knock on people who take their career seriously. I take my career seriously. But I think all those clichés about what people say on their deathbeds are true. Nobody says they wish they’d worked 14-hour days instead of eight-hour days. Nobody says that. They say, “I wish I had forgiven more people. I wish I had loved more.”

But then you think about all the people who gave everything of themselves to make something lasting. Or the message of that Lou Reed song, “Work.” [Lyrics: “It’s all about the work.”] It’s not like every moment spent not working is somehow rewarding. The moments that I spend not working are typically spent drinking more wine and watching more TV. You know? Yeah.

It doesn’t feel like a binary: Work or Meaning. No, but I tend to think [about] moving toward the direction of love — creating a life for yourself where you can give and receive as much love as possible. That is a good, worthy goal, and it seems to be central to many of our faith systems or self-help systems: getting to a place where you think that you’re worthy of love, and then being good at giving it to other people. Really feeling like you deserve to be loved — that’s actually a really, really hard thing for a lot of people, especially a lot of creative people.

I think a lot about this idea that you can’t see something clearly if you want it. If you want success too much, you’ll never be able to understand it. If you love someone, you can never really see them. I had this teacher in college named David Gelernter. He taught a class called Computer Science and the Modern Intellectual Agenda. He was famous because he was one of the first people to receive a package from the Unabomber —which now they think actually maybe wasn’t from the Unabomber. But, anyway, he wore a trench coat and had a gloved hand. Like an Inspector Gadget character. He had this theory that truly once-in-a-generation brilliant minds have something that you could call “top vision.” It’s the ability to see from above, to interconnect different studies, ideas, concepts that seem totally alien to each other to most people.

I think you have to be able to see from above. And I think if you’re like, at ground level just in pursuit of something, swimming through a rocky river just trying to stay afloat, you’re not going to see the big stuff. But I guess the issue is people want the wrong things usually, right? Or they want the right things, but for the wrong reasons. You get in the way. You know what I mean? Usually, you are what’s in the way.

I don’t think Lipsky can see Wallace clearly because he wants to be him too much. He wants to have what Wallace has so badly that it blinds him. Wallace was 34, Lipsky was 30. They were basically the same age. But I think Wallace, in the time that they spent together, was constantly defining the parameters of what he wanted his interview relationship — or this business transaction — to be, however you think of it. “These are the boundaries of what I’m comfortable talking about.” Lipsky kept overstepping [that] because he was pushing. Lipsky at 30 wanted to have an article in Rolling Stone. I think Wallace understood what he was doing and also related to it; he did it himself professionally when he would profile people. But he knew that he was in the middle of having his life changed. Infinite Jest was different than his earlier books. He knew something was not going to be the same for him, so he had a specific, unique insight into that thing that Lipsky seemed to be fascinated by: fame. How fame validates you and fills you and fulfills that empty part of your gut.

I think Lipsky understood better as he got older that this guy was not bullshitting him. He came to understand that Wallace was trying really, really, really hard, even though he was exhausted and had been doing press for months, just to be honest about what he was wrestling with.

The book didn’t fill that part of his gut. It didn’t make him happy. That’s the simplest way of putting it: no movie’s going to make you happy. No book’s going to make you happy. No achievement. If that’s the thing that you’ve been chasing, that you chase really, really hard. That’s the dirty secret, right? It’s not going to make you happy.

And Lipsky just can’t believe him. I was able to talk about these things with Jesse Eisenberg and Jason Segel, who are both famous actors and writers, with far more insight into fame than I have. I’ve seen actors just try to be endlessly humble and have real gratitude for every interaction. And I’ve seen people be real jerks to them back. It’s really hard.

But when you are not successful, and you hear someone who is successful say that it doesn’t “fill the void,” it just sounds like bullshit. It does. It sounds like false humility. It sounds like they’re hiding something.

Well, it just sounds like they’ve forgotten what it felt like to have it worse. I mean, I think Lipsky desperately, on some level — and maybe we all do — wanted Wallace to be a fraud, right?

Of course. For Lipsky, the fact that someone basically his age, in his lifetime, could write this thing that felt so unattainable, so just like, beyond what he or anybody was doing — like, there had to be some chink in the armor just to help him sleep at night, because if not, you’re just left with all your own insecurities about what you’re capable of in your chosen vocation. All you want is that thing that they have, and they’re saying it doesn’t make them happy, but they can do it 10 times better than you. So, where does that leave you?

It’s Mozart/Salieri — what if someone else actually is better than you? Measuring yourself against other people will just be the absolute psychic death of you. It’s the worst.

But some people actually are better at turning ideas into art. The amazing thing about David Foster Wallace — it’s not that he had totally different thoughts than anyone else did. He wasn’t wrestling with string theory, usually, although he’s the type of guy that probably would have. He wrestled with the exact same things we all wrestle with on a day-to-day basis. But he had the gift to talk about them in a way that was more funny and digressive and human, and just spot on, than anybody else. He could write the way we hoped that we could speak, so his writing felt like the internal monologue that we all aspire to. That’s why he connected. His writing isn’t about the story of what happened. It’s about how it happens and how it affected you.

You’re a big fan of things — No. 1 Superfan of Things. And a journalist [for this magazine], also. That seems to me to be where you get a lot of fulfillment. The summer after my first year of film school, in 2002, I went and made Coming Down the Mountain, that Kentucky short. And I got really obsessed with Bonnie ‘Prince’ Billy. We endlessly tried to use a song called “Careless Love.” We wanted it so bad for the short, and we couldn’t get it. And then I remember going to this very early screening of All the Real Girls. The very first scene is Paul Schneider and Zooey Deschanel talking, and they have this kiss, and there is Bonnie ‘Prince’ Billy’s song. And I just remember thinking, “Motherfucker.” And then the movie continued and just hit all these notes I had been trying for — the references, the environment, the world, the South, whatever. That movie and Old Joy, when I saw it, I just remember being so jealous, to the point of angry. But, I think after a couple of days, I stopped being angry and jealous, and I was just like, “Man, I am so glad that David Gordon Green or Kelly Reichardt made that movie. I never could’ve made that exact movie. They were the only people that could make exactly that movie, and I’m glad that it’s in the world, and it’s going to hopefully inspire me to make something that’s just as true for me.”

I spent the whole movie looking for clues about Wallace’s suicide — “that, there, that’s his depression, that’s what’s going to do him in!” Where’s Rosebud, right?

Yes. Where is Rosebud? There’s a Wallace short story, “Good Old Neon,” which is from Oblivion. It’s a portrait of a character that’s going to commit suicide. It describes a person who’s so intelligent that part of what destroyed him was the feeling of knowing. Like, being able to size someone up, anticipating what would transpire in the conversation or in the relationship with that person before it had actually happened. Having a brain that reduces people to archetypes and can predict what’s going to happen, which gives you a feeling like you’re going through some pantomime, a script that’s already written. Understanding that he was able to manipulate people.

And yet, desperately wanting to be present and genuine. But he can’t, because he could always take advantage of people. He’s in this endless loop of self-loathing because of it.

Yet Lipsky mostly ignores that pain and just gets aggressive and tries to ask “tough questions.” Well, [questions about pain] make for really depressing copy. And he was looking for good, easy copy.

Was he? Well, he was looking for a story about success, right? What is it like to be in the eye of the storm? What is it like to be Bob Dylan the year Don’t Look Back broke?

By the way, Lipsky, to his credit, has had absolutely zero vanity about himself through this process. He never said, “What’s my character going to wear?” He really did not care. But he fiercely defended David Foster Wallace in excruciating detail. He just wanted to make sure that we got him absolutely right. I found it very moving. And with so many of the people involved — like, for instance, Emma Potter, the costume designer — I found it the same thing. It wasn’t just that she went online and found pictures of Wallace from that time. She dug much deeper into what that actually meant. She put it in the context of his own life — him wearing Nikes in this scene, how does that correlate with athleticism? How much was the athleticism real? We looked at a lot of photos of the TV show Friends. You know, he was Manhattan, pseudo-sophisticated, so the so-slightly baggy jeans or Gap khakis or these jackets that are a little too big. It’s such a fine line, right? Or the bandana — the bandana!

Was there a bandana debate? Well, the actual truth was, at this point in his life, David Foster Wallace was wearing the bandana, and during the entirety of his time with David Lipsky, he wore it. But it’s just such a trademark. So, is it too on-the-nose, even if it’s true?

How did you decide to make this movie? Donald Margulies had adapted Lipsky’s book. And Donald had also been my teacher. He is both a fantastic writer and a fantastic teacher, which is rare. So he sent me the script and he said, “Hey, James, I don’t know if you’re a David Foster Wallace fan or you’re aware of this book that David Lipsky wrote.” And, I mean, I had David Foster Wallace’s [Kenyon Address] read at my wedding. It was one of the moments of, like, “I hope this [script] isn’t as good as I think it could be.” And it was better than that.

Did you struggle with the ethical question — not just do I want to make this, but can I make it? Should I make it? Well, is it ethically correct, so to speak, to make a portrait of anyone? Many of my favorite movies and songs and works of art are about another person or inspired by another person. I’m not the first guy to try it. People have made movies about writers before. It’s been done well; it’s been done badly.

I don’t know that I’d feel comfortable speculating what Wallace’s time was like with his family or his girlfriend. But there’s no speculation here. This is based on a recording and a transcript from an interview that was done. This is his time spent with a professional journalist, and the movie’s told from that journalist’s perspective, quite intentionally. You meet David Foster Wallace through Lipsky’s eye, through his gaze, a scopophilic gaze, directed from one man to another. The entire camera design of the movie, save for two shots, two very intentional shots, are all from David Lipsky’s point of view.

Which are the two shots? Man, this is a spoiler for people that haven’t seen the movie.

There’s one after the first night that they spend together, a night of great conversation, and Lipsky has gone to bed. There’s a shot from outside of Wallace’s house, which is a very slow tracking shot outside, where it’s snowing and it’s just pre-dawn, and you see Wallace just in his window just drinking coffee and playing with his dog. No one is watching him and he’s alone, this peaceful moment.

And then, at the very end, you see shots of Wallace dancing. David Foster Wallace does say to David Lipsky in the interview, you know, “I’m going to go to this dance later.” That’s from the tapes: “You know, I’m going to a dance.” “Where’s the dance?” “Oh, a church.” “A church? What kind of church?” “A Baptist church.” “Why Baptist?” “You know, because Baptists can dance.” All that. But the truth is, like, whether David Foster Wallace actually was going to a dance or just wanted to get Lipsky out of his house, what kind of dance it was, whether it was a sober dance, whatever it was, we can’t possibly know. [The last shot] is Lipsky’s sort of mind’s eye view of how he would like to imagine Wallace. Maybe it’s a bit of truth, maybe it’s a bit of bullshit, but that’s how he wanted to remember him — in this ecstatic state.

Are cinematic rules like that important? I think having some discipline or values system of how you’re going to make something, being able to articulate it, making rules for yourself, even if you’re going to break them — it’s really important. Part of the ideology of how I was taught was there are a couple of simple questions that you ask yourself when you’re writing a scene or when you’re directing a scene. The most basic one is: whose scene is it? Every scene is someone’s scene. If you’re not asking that, then whose is the point of view? Is it God’s?

If you haven’t asked that for yourself and really answered it, even if it’s a total ensemble, even if you’re making like, Nashville or Short Cuts, then it’s chaos. The camera can go anywhere; you have no perspective.

It is the question. It is the question. The secret question. Answer it for yourself, and you’ve ruled out 90 percent of the places where your camera might go, if not more.

What were your other references? There’s lots of movies that I talk about, like Withnail and I and Dont Look Back. One thing I thought of was this song, “New Orleans Instrumental No. 1” off [REM’s] Automatic for the People. I knew that that had to be at the beginning of the movie and I knew that “The Big Ship” by Brian Eno had to be at the end. That was sort of going to be this emotional journey, the emotional pitch that I wanted the movie to sort of trace. More and more I think of the way certain albums make me feel. And that’s what I kind of think about with the movie, sometimes, is I want this movie to make me feel like Blood on the Tracks or Another Green World or Murmur or something like that.

How do you map out your movies? Do you draw actual maps, or do you do notecards, or…? I think a lot about transitions between scenes. I think about the individual scene — in most scenes, there’s conflict, and it’s usually that one person wants something from the other one that they can’t give them. And hopefully, in a good scene, there are several shifts in the balance of power. A scene has its own arc, and your movie has its own arc. In thinking about transitions, I think of what’s going to be the last image of this scene and what will be the first image of the next? Overall, I do think of it in terms of, like, going from hot to cold, from bright to dark, from close to wide. Hopefully it never feels cerebral; when someone sees the movie, they’re never thinking that I was thinking that. Hopefully you just feel it, like there’s a subtle little heartbeat in the film.

In terms of archetypes, I do think of where this movie would be shelved, in a hypothetical video store — which may not exist anymore. In a very superficial way, it could be put on a shelf with other journalist/subject films, like Frost/Nixon or Almost Famous. Beyond that, what’s the internal story? For me, the internal story was: this was an unrequited love story. It’s an unrequited platonic love story, in the way that Lost in Translation is an unrequited love story, Brief Encounter is an unrequited love story, Casablanca, an unrequited love story.

It’s an unrequited love story because David Foster Wallace is never going to love Lipsky back. I mean, I think that’s a question. Listen, there’s the really awful version of this movie, which is two talking smart heads just talking at each other endlessly, right? A movie that’s just from the neck up. The more interesting one, the one that I think that’s true, the one that I would want to see, the one that I tried to make, is one that has real emotion, real hope and fear and anxiety about the desire to be affirmed.

That is the trick of the movie — you’re always wondering, who’s using who? Who is manipulating whom? And they both badly want a genuine connection, but maybe for different reasons, if the reasons why matter at all. I think it’s safe to argue that this was a deep, deep connection, for [Lipsky], at least. But it’s also two people with an agenda. So maybe they’re being genuine, but maybe this was an elaborate bit of dinner theater or a tap dance or a chess game or whatever the cliché is. They’re just performing for each other endlessly, playing off what they think the other person wants because they both understand the other person’s job in this situation.

Wallace is accused repeatedly by Lipsky of intellectually slumming it, or intellectually being faux, pretending to be just a regular guy in a fake way. Imagine having spent several days with someone, and someone accused you of that, essentially discrediting every word you’ve said and action that you’ve done. Especially for someone who’s wrestled with those issues so much, it’s probably very painful. It would be like, “What the fuck is the point of any of this?”

I think Wallace desperately, desperately, desperately wanted to be present and to find joy in being present in the company of other people. And I think, like many people who’ve wrestled with depression, finding that joy could be very hard.

Could Wallace just see more than other people could? Is that what all great artists have? And is that what Lipsky’s character is so jealous of, and why he can’t take his pain seriously? Have you ever been to Anne Frank’s house in Holland?

I haven’t. Okay, so Otto Frank, Anne’s father, was being interviewed on television, like 20 years after the end of World War II, like, the mid-60s. The interviewer says, “Did you think that your daughter was exceptional?” And he said, “No. I thought she was a pretty ordinary girl, just interested in the same thing that other girls were interested in. And then, when I read the diary, I was shocked. I realized I didn’t know her at all.” He said, “The only conclusion I can make is that children are always an utter mystery to their parents,” which I extrapolate to mean we’re all mysteries to each other. There’s a limit to how much you can ever know anyone else. That revelation can be really terrifying, when you find yourself in a serious relationship or when you question any relationship — it all feels very abstract and kind of … built out of smoke. But I do think there’s certain things, certain very universal experiences, even dumb things, like primetime TV and 7-Eleven Slurpees or whatever, that are just so universal and stupid, that it’s the foundation of our humanity. Far more than highfalutin conversations about God, which is so subjective. But we can definitely say, “I like going to watch this silly John Woo movie and watch stuff explode. It makes me feel a little bit better than I did before.”

Those are some of the themes Wallace was always talking about — Americana, banality, sports, fast food. He would write about philosophy, and then he would write about a porn convention. He would use a folksy Americana thing like a lobster festival in Maine to write about the ethics of taking something else’s life, and our inability to care that it feels pain. It was these normal, everyday things. It’s not a conscious high/low, like, “Oh, I am erudite, I like art and trash.” It’s more, “Let’s just like the stuff that makes us really happy and be honest with ourselves.”

The key is to like what you like without qualifying it all the time. Like what you like without qualifying it. That’s having an honest experience. I think that’s it, right? I think Wallace was just, like, trying really hard not to qualify the experience he was having, even though he was the subject and Lipsky was the journalist and the stakes were Rolling Stone and the angle was about his public perception. Like, I think he genuinely wanted to just enjoy the experience for what it was. He really wanted to, but there were certain limitations. One of them was just that he was tired and just wanted to go home.