Writer David Lipsky’s greatest contribution to the literary world to date might be a recounting of a lengthy encounter he had with a fellow author. Back in 1996, journalist and novelist Lipsky was assigned by Rolling Stone to write a long-form interview piece with then rising literary superstar David Foster Wallace. At the time Lipsky travelled to Illinois to profile Wallace at his home, the behemoth novel Infinite Jest had just been released and the author was finishing up a major book tour. Infinite Jest was heralded by many as a sort of “second coming” for the American novel, and Wallace’s profile reached stratospheric heights in the literary world. Lipsky spent five days in the late winter of 1996 travelling with Wallace and observing his behaviour. It was an experience that would change Lipsky’s professional outlook for the rest of his career, coming to recognize Wallace as a kind, gentle, gregarious figure who had an uneasy relationship to self-promotion.

It would probably be surprising to some to hear that Lipsky’s interview ultimately went unpublished by Rolling Stone for a variety of reasons. Wallace continued his career, and Lipsky continued his, but the interviewer would always hold the time spent with his subject close to his heart. It wasn’t until David Foster Wallace committed suicide in 2008 that Lipsky would be able to share his interview with the world, and in the process help many to remember Wallace as a writer that touched a lot of people.

Lipsky would eventually pen a piece looking back on the interview in 2009 for Rolling Stone that would not only win a National Magazine Award, but would also be published as a book that takes on the style of Lipsky and Wallace conversing back and forth about any number of subjects professional, academic, or mundane. Lipsky’s Although Of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace was published in 2010 to a great deal of acclaim and a spot on The New York Times’ bestseller list. It was also cited by many close to Wallace as an accurate depiction of what the writer was like as a person, and not merely as some sort of mythical literary icon.

In 2015, Lipsky’s epic interview was adapted for the big screen by screenwriter and Pulitzer Prize winner Donald Margulies and director James Ponsoldt (The Spectacular Now, Smashed, the upcoming Dave Eggers adaptation The Circle) as The End of the Tour with Jesse Eisenberg portraying Lipsky and Jason Segel stepping wonderfully into Wallace’s seemingly unfillable shoes.

Mr. Lipsky travels to Toronto next Monday, April 17, for a presentation of The End of the Tour as part of TIFF’s Books on Film series at the TIFF Bell Lightbox (hosted by Eleanor Wachtel of CBC Radio’s Writers & Company). We caught up with him on the phone from his home in New York to look back on his interview, the book, perceptions of the film, and a lovely, seemingly incongruous moment from both the book at the film that stands out as a memorable point in Lipsky’s time with Wallace.

I often find myself as a journalist having to explain to people this notion that no matter how famous an interview subject can be that sometimes they go unused or unpublished for a variety of reasons. After your book and your chats with David Foster Wallace became public knowledge, were people surprised that the interview wasn’t used sooner?

David Lipsky

David Lipsky: Yeah. I remember, and this is in the movie and in the book, that David always had mixed ideas about publicity, anyway. He knew that he was doing great work, but he also knew that the work of doing publicity was always a bit greasy. And I mean greasy in the way that it can make you feel good doing publicity, but not make you feel good in the way that doing good work makes you feel good. He began by saying that if this was the reason that he was writing that he needed a better reason for writing than getting all this attention. He had a great word for it, and he called it “the fuss.” He said that the fuss was like getting a shot of heroin right to the cerebral cortex because that attention can feel so good and be so satisfying in a way, but he questioned if he would only do this or feel this way every five years or so whenever he got a book done. That couldn’t be what motivated him as a writer, and that was what made him so leery of the publicity process.

In a way, after I spoke to Jann [Wenner from Rolling Stone] and learned that it wasn’t going to run, I think it was puzzling to some now in hindsight, but a relief in some ways to David. When I got back from Illinois from spending time with David, I was sent back out on another story, a story that comically enough was about substance abuse, since one of David’s major themes in the world of Infinite Jest were these ideas behind addiction and consumption among North Americans. One of his ideas was that the way modern life works is that we get addicted to stuff. We can get addicted to Game of Thrones. We can get addicted to yoga. We can get addicted to raw foods. We can’t approach everything in  moderation, and the way that he put it was that we were all dying to give ourselves away to something. For him, the metaphor for that was substance addiction, which was a huge thing in the book and one of the things I was supposed to look into while I was in Illinois. So it was funny to leave Illinois and go to Seattle, just a few miles south of Canada, and live with heroin addicts for a month.

That was what Jann wanted me to do in April, so when that story closed in May, at that point when I wanted to get back to David’s story, it was now talking about a book that had come out in February, which as you know, for journalism that’s basically ancient history. To have a story come out in May for something from February just doesn’t happen. They knew that I was passionate about it and that I had put the work in, but they just couldn’t run it.

So when I had to pass that along to David and his agent, I said it was good news and bad news. I said it was good news for David because he had questions about how he was going to face, again the term he used was “greasy thrill,” and how much he was going to get addicted to that. It was hard to tell him that piece wasn’t going to run because everything he talked about was kind of great. So a lot of times I would tell people about it even though it didn’t run.

The way I finally ended up doing the piece in 2008 and it ran and won something down here called the National Magazine Award, it happened as a result of me telling so many people about how great the experience of travelling with him at been and how awakening and eye opening it was. I did a lot of work for National Public Radio, and when David died, my producer at NPR called me and said, “Do you want to talk about him on air? Because you always told me how much he meant to you as a writer and how important that trip was.”

I didn’t want to do it because I was really sad that he had died. My mother also lived in New York City at this time, and when she heard that David had died, she came up to my apartment. I lived about five miles from her. I lived uptown and she lived in Chelsea. She came to sit with me because she knew how upset I was going to be. So the people at NPR, when they called, I said that I just wanted to sit with this feeling today and spend some time with his writing and not think about writing or saying something about him.

There’s a thing with writers in that when they die, everything they wrote will be analyzed or read for clues as to why they died. That would be bad because what you lose when you do that is you lose the sense of a living person. You lose David. His work was so amazingly vivid and alive, and he was so amazingly charming, and all that would be lost in such a reading and people would only see his life as a shade of constant gray that would be targeted towards his death. When I expressed those fears, that’s when they allowed me to go on air and talk about how great he was as a person, and then Rolling Stone got me to do a different version of the piece. They heard me on NPR, and they heard my concerns, but they were also receptive because they said and remembered that he wrote for their magazine. He won a National Magazine Award with them for writing about the John McCain campaign. (laughs)

In a way, those frustrations with how I felt about how people would remember him let to the pieces, which led to the book, which led to the movie. I had talked with all my friends and people that I had worked with to spend a week in the company of someone I knew was doing the best prose work in all of North America.

This is obviously such a personal project for you, so even though The End of the Tour has a Pulitzer Prize winning screenwriter in Donald Margulies and a critically acclaimed filmmaker like James Ponsoldt attached, was there any trepidation regarding how the film would interpret your feelings about David Foster Wallace and what that time meant to you? More specifically speaking, were you afraid that because you, David Lipsky, are alive and David Foster Wallace is no longer with us, that the film would be more about you than David Wallace?

David Lipsky: There would have been anxiety, for sure, if I hadn’t been working with Donald. Donald contacted me very shortly after the book came out, and he is someone who cares very much about artists. One of the reasons I was so eager to work with him was that, and I was willing to trust him with the material. He has written about writers before. He wrote a great play about a short story writer called Collected Stories, which was a finalist for a Pulitzer, and he wrote a great play about painters called Sight Unseen, which was also a finalist for a Pulitzer. He won his Pulitzer for a play called Dinner with Friends. All of those plays tend to deal with fixed periods of time, like the one David and I experienced. Sight Unseen is about a weekend spent with a painter visiting another painter a former lover of his. Dinner with Friends is about these friends having dinner at different periods.

He seemed to know and understand from the first time we went out and had coffee that reason the book exists and operates is to show what this person was like. In the book, you’ll see that I cut my questions back as far as I could, and I think as you probably know, a lot of journalists tend to do that, anyway. I never wanted the reader following me. If you go back and check in the book, you’ll see that sometimes my questions are just the start of a question, three or four dots, and then the end of the question. I didn’t want the subject to be on me. I wanted to write the book that I wanted to read about David. Here is this person, and here is what they were like hour by hour.

When I talked with Donald, that was one of the things that he liked the most about the book. He found a way within the material someone who has kept this subject alive, whole, and independent. There was never that anxiety with Donald because we talked about that at the beginning.

James Ponsoldt, then, was a former student in Donald’s playwriting class at Yale. So Donald put me in touch with James, and James had been a huge fan of David’s since high school. He had read all the books and my book before we started with the movie, so together we were able to keep this alive, and the focus on David, and not about me.

Something that your book and that the film captures very well was that David was admittedly a genius, but one that had the qualities that we like to hold our best friends to, making him a person that those close to him would feel strong and warmly towards. I know to some degree that some of David’s former friends – perhaps most notably Glenn Kenny’s piece in The Guardian – have been critical of the film. Yet, despite the criticism of the film itself from some people, you remain largely at an arms length from such criticism. Why do you think that is? Do you think this has something to do with people wanting to remember someone they lost in their own way and find a dramatic recreation of such events as a tarnishing of those memories?

David Lipsky: Well, with Glenn, it’s interesting. Before Glenn was working for The Times and before he wrote that piece in The Guardian around the time of the film’s release, he posted on his blog Some Came Running where he wrote this incredibly warm piece about the book, which you can find very easily. He called the book a gift, and that the book was the man that he knew.

When the piece in Rolling Stone ran in 2008 and after the book came out, I got letters, calls, and emails from friends of his and people who were close to him in other ways, including people that I had interviewed for the book and for the Rolling Stone piece. What they had said is kind of hard for me to explain, and what I had to explain to them about what I wanted to do with the book was equally hard. Normally what would happen with this kind of material is that it would get turned into an extended biography. A good friend of mine, D.T. Max wrote such a book called Every Love Story is a Ghost Story, and he wrote a more standard biographical take on David, which is great. But what I had really wanted to do was just show what this person was like, so it was just what I observed about David, and I think that’s how we react to anyone we have great feelings towards. We bring to it what we witnessed. Have you read a lot of David’s writing?

A fair bit.

David Lipsky: A great place to start is with his journalism. About three or four weeks before Infinite Jest came out, David had a piece published in Harper’s called Shipping Out, which is about getting stuck on a cruise for a week. Harper’s knew how his brain worked and how he would react to it. David was the most wide awake writer that we had for a very long time, but he’s also really insightful and funny. They thought it would be great to send him on a cruise so we could see what he sees and see this world through his eyes. We can always only see things as we see them through our own eyes, and when you look at something like Infinite Jest, what you’re curious about is how they experience life on a minute to minute basis. You ever read The Catcher in the Rye?

Oh, yeah. Several times.

David Lipsky: There’s a great thing said early in the book, which is that when you read a great book, you wish the writer of the book was a great friend of yours that you could just call on the phone and just ask them for their opinion on a list of stuff. You know you love a writer when you want their opinion on everything in the world.

When I was thinking about what David was like and after reading a bunch of what was written before and after 1996, I was remembering what it was like to be a fan, and my question was always, “What is it like to be this person who is so awake and alive?” What are they like having their first Pop-Tart in the morning. What are they like when their flight is cancelled? What are they like when checking into the hotel? What are they like when they are meeting new people? Are they going to be awake and alive in the same way that you see in their writing? That was the great thing about doing the book in the way it was done. You don’t have to wonder about what it would have been like to spend time with this person because here you literally are spending that time with the person. That was so gratifying to me as a fan, a reader, and a writer. People were writing me and saying that this was the guy they knew. That made me so happy that I had found a way to preserve the charming and wide awake person that he was.

This might sound like a silly question to end on, but there’s something that has been bothering me since reading the book and seeing the film. Both include an aside where you go to the movies and you see the John Travolta-Christian Slater film Broken Arrow. We see and learn what David thought about it through the book and the film, but all we know about your experience with the film is that you had seen it twice. You never gave your own opinion on it, so what are your honest feelings about Broken Arrow?

David Lipsky: (laughs) Sitting through it twice was a small price to pay to watch David’s reactions to it. (laughs) That’s what I think about it. I’m a fan of that kind of movie, though, and sitting through it twice was a small sacrifice to see his reaction to it. That’s a great question, by the way. It’s still making me laugh just thinking about it all.

I was honestly just watching David when we went to see it together. I’m actually a John Woo fan, but Broken Arrow isn’t my favourite. I love The Killers most of all, and I think Face/Off is in certain ways a better movie than Broken Arrow. But David had always talked about loving movies where things blow up and sitting towards the front of the theatre to watch things blowing up better. What a great thing to watch him watching that movie. Just to watch this person who had written this brilliant novel is a thrill. He even puts it best himself that films like that make him forget that he’s David Foster Wallace, that he has a pimple on his nose, and things to do. To watch him wincing and smiling throughout the film and the explosion scenes was something that couldn’t be replicated. As such, I have such fond feelings for Broken Arrow, and now reliving it with you makes me want to relive those scenes again.

But for people who don’t like John Woo, David gives such a great synopsis of the movie, which is that it’s a film where you get to see John Travolta get hit in the chest with a thermonuclear device and get carried out of the frame. That’s really all you need to know about the film itself. (laughs)

And it all goes back to what you were saying before… One of the reasons why people love David’s work so much is because when you’re reading him, he’s expressing what you think like when you’re thinking at your best. When he talks about what he calls his “regular guy-ness,” he’s referring to ways that he feels different from other people, but how he’s always listening to them. For him to have talked about loving those movies and watching him respond for the first time to explosions on screen that he hadn’t seen before was to see that, yeah, you can be alive to the world around you and still be a great writer.

The piece that he won the National Magazine Award for Rolling Stone about the John McCain campaign contained as the last words: “try to stay awake.” That’s how that piece ends and that’s the advice that reading all of his writing gives in some way. If you are awake, life can be boring and repetitive, but it’s thrilling if you stay awake. To get to watch him staying awake through something like Broken Arrow? Fuck no. I would never trade that for anything.

About The Author

Andrew Parker
Senior Writer

Andrew Parker started fell in love with film growing up across the street from a movie theatre. He began writing professionally about film at the age of fourteen, and has been following his passions ever since. His writing has been showcased at various online outlets, as well as in The Globe and Mail, BeatRoute, and NOW Magazine. If he's not watching something or reading something, he's probably sleeping.

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