Are you one to meet your heroes? By reading, watching, listening to their work, do you feel a connection to them? Or are they enigmas whose mysteries you need to crack?

In the world of contemporary letters, few figures loom as large as David Foster Wallace, whose sprawling, wickedly funny, fiercely observant works grappled with both the necessity and near impossibility of sincere, non-ironic expression in the age of commodified mass media and a meaningless public discourse. In essays about punctuation and cruise ships, tennis stars and cooked lobsters, and in stories and novels including his protean cultural phenomenon, Infinite Jest, Wallace told shaggy-dog tales laced with moral urgency and with the intonation of a friendly Midwesterner determined to help you make it safely to your next station in life.

In 1996, the young writer David Lipsky was assigned by Rolling Stone to accompany Wallace over five days of his Infinite Jest book tour. Lipsky’s story was, however, never published until after Wallace committed suicide in 2008. Then the journalist published Although of Course You End Up Being Yourself: A Road Trip with David Foster Wallace. You could call it, perhaps, a biographical miniature. Or a long-form dialogue. Or, perhaps, a memoir of youth in the guise of a conversation.

Now, that book of Lipsky’s is a movie, The End of the Tour, by James Ponsoldt. Adapted by the Pulitzer Prize-winning playwright Donald Marguiles, the film stars Jason Segal as Wallace and Jesse Eisenberg as Lipsky, and it premieres today at the Sundance Film Festival.

When I heard Ponsoldt, whose films include Off the Black, Smashed and The Spectacular Now, was going to be making a movie about David Foster Wallace, I was excited. He shares with the author an aversion to sentimentality as well as a desire to move people, to connect. He’s also one of the most ferociously well read friends I have, which leads into a full disclosure that, given Ponsoldt’s prolific filmmaking, is becoming a regular occurrence here at Filmmaker. Robin O’Hara and I produced Ponsoldt’s first feature, and he’s also an occasional contributor here at the magazine. Even if all of that wasn’t the case, though, I’d be excited to see The End of the Tour tonight. Needless, to say, I haven’t seen it yet, and I am learning most of what I know about it in this conversation, recorded a few days ago.

Filmmaker: So, we’re talking a few days before Sundance starts. Is the film done?

Ponsoldt: Yeah, we’ve been done for a while. Compared to past experiences, it’s been really leisurely. We shot in the winter, and we were picture locked by the summer. And then we landed a really great composer, Danny Elfman. He had a window of time [in the Fall], and it was worth waiting for him. And then we got this really great colorist, Bryan McMahan, who does Terrence Malick’s films, and because we weren’t sprinting to finish we could put everything on pause for seven weeks and wait until all these amazing people were available. So it was nice, and it certainly benefited the film, as opposed to what I’ve experienced in the past, which is, “It’s January 4th, let’s finish and sprint to Park City!”

Filmmaker: So, when did you first encounter the writing of David Foster Wallace? When did he make an impact on you?

Ponsoldt: I was aware of David Foster Wallace from when I was in high school in the mid-‘90s. I was writing for an alt weekly, a music and arts magazine in Athens, Georgia called Flagpole. Everyone else [on the writing staff] was significantly older — college students, grad students, post college — and David Foster Wallace was a name that was thrown around a lot. I remember when Infinite Jest came out, I was finishing up high school and it was this sort of big, intimidating, exciting thing. I finally tackled it my freshman year in college. I spent the entire winter — three or four months — reading it, and I would say it significantly altered the way that I thought about writing, the way I thought about the potential for storytelling and about how honest and strange prose can be. It was that book and The Moviegoer by Walker Percy — which is an incredibly different book, but definitive for a different generation — that, I think, set the course for the type of fiction that I sought out after that.

Filmmaker: You said it changed the course of your own writing. Can you elaborate a little bit on that?

Ponsoldt: Although I couldn’t have articulated it at the time, and this is a weird way to put it, but you know Werner Herzog’s idea of ecstatic truth, where the documentaries have some fiction-like qualities and the fiction films have some documentary sort of qualities? I think that [applied to] Wallace’s nonfiction essays, which were fictionalized to some degree. And then, with his fiction, especially Infinite Jest, which is seen as a big, intimidating postmodern book, it’s incredibly personal, you know what I mean? All the bells and whistles sort of hide that fact. I think a lot of what the characters in that book are wrestling with, whether it’s issues of being a young athlete, feeling the pressure of the world, or addiction, which is a large part of that book — a lot of that was very much in my consciousness, in my life and world at that time. That book, and a lot of the characters in it, gave voice to a lot of things I was personally struggling with, and in a way that was hugely confessional, hugely creative and funny as all hell. And nothing was really sacred in it, you know?

I was a huge consumer of entertainment at the time. I grew up a television addict. Throughout my adolescence, I probably watched five or six hours of television a night, and I felt my interests being pulled in every single direction and all at once by books, magazines, music, and the early internet. And that book felt as ADD as I felt. [Laughs] In reading David Foster Wallace, I found someone who it felt like was writing exactly to me. The book felt like what it was like to be alive in the mid-1990s, which is to say to be pulled in every direction by all things at once and to have media seduce you, to sell you images that are both real and unreal. It felt like this was a guy who got it in a way that no other writer I had read to that point really did. The idea of [using] parentheticals, a lot of asides, a lot of footnotes, etc., that became really commonplace after [Infinite Jest]. That became sort of the affectation that Wallace was known for, but I think [his use of those devices] came from a genuine place of someone trying to express something really personal.

Filmmaker: So the source material for your film, David Lipsky’s book, is based on a Rolling Stone interview that was conducted over the course of a few days, correct?

Ponsoldt: Yes.

Filmmaker: When did that interview occur in Wallace’s life?

Ponsoldt: The interview was in March of 1996,when Wallace was on the tail end of the book tour for Infinite Jest. Wallace had started publishing in the late ‘80s and was known in literary circles. His publisher pushed the book pretty hard, and the literary world was waiting for it. Wallace did quite a bit of press, and this [interview] was at the end of [this period]. He had worked really hard for years on a really tough book, and the world didn’t deny it or let it slip by. It was received positively — an amazing affirmation. But, by the end of this tour I think Wallace was really tired of having to talk about the book. And that was when David Lipsky got sent out by Rolling Stone. You know how it goes, and so do I. A lot of subjects know better than to have a journalist shadow and stay with you for days. But for whatever reason, Wallace said yes, and Lipsky accompanied him for the tail end of the book tour.

Filmmaker: While I’ve never been a fan of the cradle-to-grave biopic, I have always liked the kind of miniature biopic, films about real people set during specific moments of their lives. But when making such a film, how do you avoid — or do you not avoid — allowing the film to be informed by the entirety of your subject’s life? In other words, how do focus your vision on just those days?

Ponsoldt: Lipsky is a first-rate journalist, as was Wallace, and our film is based on [Lipsky’s] amazing book that came out in 2010 following an article that won a National Magazine Award in late 2008. It’s based on what these guys actually said, so, there’s a weird quality of real verite to this: these guys actually said this, actually did this. The tapes exist, and they were made available to me, and I made them available to the actors. You know, there are films like The Hours and Times, which I love, that kind of speculate about a period of time [in their subjects’ lives]. But there’s no speculation here. [Laughs] It happened, and there’s a record of it. For me it’s more like Don’t Look Back, the Pennebaker film, where you’re recording in real time someone who is young, brilliant, talented and in the eye of the storm. It’s just capturing a tiny moment of time and how they’re engaging with what the world is bouncing back at them.

It is also worth saying that this is David Lipsky’s memoir. This is David Lipsky’s account of this time and how he was affected by this time with Wallace. The entire movie is told through his eyes. Lipsky was 30 years old when he went out and spent this time with Wallace, and Wallace was 34. Lipsky had just published his first novel as well and had had a collection of short stories. There was, I think, a lot of competition and a sort of emotional transference. That things get blurry in this relationship comes from the fact that these are two guys basically at the same point in their lives, but Wallace had just written a book that sent shockwaves in the literary world. There’s something inherently subjective about writing a book that includes another person, and the movie, I think, uniquely acknowledges the blind spots that people bring into those situations and the weird dynamic that comes up when a journalist relates to a subject and gets close to them.

[The End of the Tour] is also a story about meeting someone you’ve admired from a distance, so in that regard it’s an unrequited love story. It’s about meeting that person who you’ve built up, whether it’s an artist or an estranged family member — someone who has taken on an entire constellation of emotion and meaning to you, and who, at the end of the day, is a total stranger. And who, when you do find yourself in their proximity for some time, [your] relationship [with them] is complicated by their own messy humanity.

Filmmaker: How do you think the film will play for people who don’t know the work of either of these writers?

Ponsoldt: You should not need to know these guys’ writing to appreciate the film, otherwise, it would be a pretty limited audience and an incredibly cerebral film. Films like Withnail and I, California Split, My Dinner with Andre and The American Friend, the Wim Wenders film, were as much frames of reference as Don’t Look Back and The Hours and Times — or Social Network or Good Night, and Good Luck. It’s a “hang-out film” about a really complicated relationship. On the surface, Lipsky, played by Jesse Eisenberg, is a journalist going to get a story… but Lipsky, in some ways, is one part Ratso Rizzo and one part Salieri. He really admires [Wallace] on a deep level, and on a certain level he kind of wants to be him. But how could he not want to, because we all would aspire to that. That was the great quality of David Foster Wallace’s writing. He could articulate the interior voice of all of us as we deal with the banal stuff of every day life — sports, malls, porn, etc.

Filmmaker: Tell me about Donald Margulies, who wrote the script. What qualities did he bring to the adaptation? And did you get involved with the project through Donald?

Ponsoldt: Donald was my playwriting professor in college. He won the Pulitzer Prize for Dinner with Friends, and then I had him the year after that. I was so intimidated by him before I knew him, and then, once I had his class, he was just a real mensch and a wonderful teacher. My father was a college professor for over 30 years, so I admire great teachers. David Foster Wallace was a great teacher too, as is David Lipsky, who teaches at NYU.


I stayed in touch with Donald and would see his plays when they were produced on Broadway or would come out to the La Jolla Playhouse, the Geffen or South Coast Rep. And he saw my films and was really supportive. I had just been at Sundance with The Spectacular Now. I’d been back for about a month and was finally working again on an original script, and then Donald reached out to me from the blue and said, “Hey James, I don’t know if you’re a fan of David Foster Wallace.” [Laughs] He had no idea that I was a mega fan and that I’d even had some of Wallace’s Kenyon Commencement Speech read at my wedding by Trevor Morgan. And I had read David Lipsky’s book and really admired it as well. He said he had adapted the book for Anonymous Content, and, of course, I admired Anonymous for everything from Frozen River to Eternal Sunshine. There was a real charge; it was one of those emails that sits in your inbox and you’re like, “I hope this isn’t as good as it could be.” I kind of wanted it to not be great because I was very excited to work on my own script. But it burned a hole in my inbox and was one of the quickest reads I’ve ever had, and I think it’s the most beautiful thing Donald’s ever written. What I loved about it was the absolute restraint. It’s never histrionic. It’s never exploitative. It’s incredibly subtle.

So immediately I knew I had to tell this story. You [make] movies about things that you can’t stop thinking about, about characters you love. You try to engage with questions that really haunt you. When I was 15, 16, starting to interview people in bands and growing up in a college town with a lot of indie music, I romanticized tortured artists, musicians with issues. You remember the playlist I made for Off the Black, right? It was Syd Barrett, Skip Spence, Roky Erickson, Townes van Zandt, Brian Wilson. I had this romance for that. And then, when I got into college, I had friends who dealt very seriously with mental illness. I had a number of friends who were artists who committed suicide, and now I don’t find any of that romantic at all. And I realized that most depictions I’ve seen of that in films really get the details wrong. They become a sort of pornography of pain, of misery. They feel really immature, actually, and lacking a central humanity and a real understanding of what it’s like for the people who love people who are suffering and who have a disease.

What was exciting to me was that this film would be about a moment in time when Wallace was 34 and very healthy, very successful and very happy. He was sober — and I’m not saying anything here that’s not out in the public sphere, like in D.T. Max’s biography. He had been on antidepressants, on Nardil, for a while. He was teaching. His book had come out and people loved it. Things were going really well for him, and he was, by all accounts, radiant. He was an amazing teacher. When he came to New York to meet with editors for a magazine piece, people came out to hear him talk because he was so charismatic. And, like with people I’ve cared about who have wrestled with depression, it’s a very private thing. If you don’t know them intimately, especially the artists, you have no idea how much they’re suffering. They really are defined by their light, by the radiance of their smile, the quality of their infectious energy. And that’s this period of life for Wallace, this tiny, tiny window.