Twenty years ago, David Lipsky talked his way into interviewing David Foster Wallace. The two travelled together on the last five days of the Infinite Jest tour. The interview wasn’t published in Rolling Stone until after Wallace’s death—when Lipsky’s piece won the National Magazine Award—and Lipsky used the conversations and tour notes (with its record of cigarettes, arguments, and bad food) to create his 2010 book, Although of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace. This year, the book was turned into the movie, The End of the Tour, with Jesse Eisenberg playing Lipsky, Jason Segel as Wallace. It premiered at the Sundance Film Festival. The New York Times wrote “Mr. Segel’s performance—empathetic, nuanced, whip smart—left the packed theater breathless.” The film was released on the last day of July.
Lipsky’s own career is wide-ranging, featuring brilliant examinations of complex subjects like the heroin addiction in ‘90s Seattle, West Point, and Heath Ledger. As an undergrad, he wrote “Three Thousand Dollars,” a short story that would appear in the New Yorker, get selected by Raymond Carver for the year’s Best American Short Stories collection, then become the title story for his first book. He received a GLAAD Award for a year spent chronicling the lives of at-risk gay and lesbian teenagers. In addition to Although of Course and Three Thousand Dollars, he’s also the author of the novel The Art Fair, the bestselling Absolutely American, and the upcoming cultural history of global warming The Parrot and the Igloo. He teaches in the MFA program at New York University.
I met David Lipsky at the Texas Book Festival, where he was promoting Although of Course, then was lucky enough to take his nonfiction workshop during the Aspen Summer Words festival. He is, as you can see in this interview, intimidating in conversation. Quotes and literary examples come to his mind instantaneously (he often repeats them verbatim—I checked) and he has this wonderfully manic vibe. Waves of contagious excitement rush out of him, and the first thing I want to do every time we finish talking with him is run off and read every mentioned book. He’s a kind of library Tarantino.
There have already been several great articles and interviews with Lipsky about the movie and his relationship with Wallace. In this conversation, I focused more on Lipsky himself: his thoughts, career, and perspective. The transcript below has been shortened and edited.
The Rumpus: So I went and watched My Dinner with Andre [a 1981 film that’s basically a long dinner conversation between Wallace Shawn and Andre Gregory about depression, spirituality, and acting] before seeing the movie, since reviews have compared the two films. It’s hard to imagine such extended conversations taking place now. Do you think an audience trained on digital social interaction will see this film as sort of romantic, or maybe foreign?
David Lipsky: I have a few thoughts for that. One is that if conversation becomes a foreign idea, we have larger problems than whether or not people will get the movie. We have our conversations by entering an electronic space now, as opposed to closing the door and setting down the chairs facing each other. I think there’s a few different ways we all communicate, email and texting and Twitter and Facebook, those are all preludes. They’re like the NASA staff, stages of the rocket. They’re the very intricate and complicated ones before we actually get in our car and open a door and sit down and face somebody. And, with magazines taking a little bit of an economic hit, it’s hard to imagine them flying someone out to sit with a writer whose name people don’t really know yet.
Rumpus: It’s been twenty years now since the events in your book and the movie, since you’re standing on Wallace’s driveway about to leave. How have those twenty years turned out for you, compared with how you thought they’d go?
Lipsky: Huh. I kind of thought I’d write more fiction. When I went to work for Rolling Stone I had just finished Art Fair and I was talking to a friend of mine who also wrote fiction and nonfiction—the writer David Samuels—and I said that one of the neat things about being in school is that people assign you things to think about that you become choicelessly expert in; things you may or may not have an affinity for. That seems like a drag when you’re in school, but there’s something really nice about not being victim of your own tastes all the time. In grad school our chairman was writing an endless book about Borges and Poe. Every year he’d have the incoming students read all of their work to see if they picked up something he’d missed. I didn’t like it at first, then it was great. I loved Borges. I actually loved Poe. And when you leave school there’s a great thing where you’re on your own cultural reconnaissance, like everything you read is a reflection of you. And that gets limiting. So I remember saying to my friend that it’d be nice to spend a year having other people telling me what to think about, what to really become expert about. I think I would be surprised if he had said, “David, it’s going to be two decades.”
Rumpus: I guess the follow-up question to that is, Absolutely American came out of a Rolling Stone piece, Although of Course came out of a Rolling Stone piece, you’ve got this upcoming climate change book you’ve mentioned, is that also born out of a Rolling Stone piece?
Lipsky: It absolutely is. The great thing about journalism is that you can be reading somebody, like when David’s first book came out, we were passing it around. And it was great. Then he started doing his tremendous pieces for Harper’s. We knew Infinite Jest was coming in, and so for the Rolling Stone Hot List, we tried to get him on that summer because the book was dropping in January. His cruise ship piece came out, and it was thrilling—people would call and read you passages on the phone—then his novel was out and all of a sudden I was in his spare bedroom listening to David Wallace tell his dogs to cut it out so he could go to sleep. That’s just one of the magical wormholes that journalism cuts through the walls. In the same way all I knew about West Point was that if you got a certain score on the PSAT you’d get their information in the mail, and then all of a sudden there I was in with company G4, in at 5 a.m. morning formation. Or there I was in Beast Barracks, marching with a pack on.
Rumpus: When you pitched this idea of going to live at West Point to Rolling Stone, how did that work from a logistics standpoint? Were you still doing the occasional other thing while you were there?
Lipsky: No, you couldn’t really, because it was very involving. The way that happened was, by the late ‘90s, we hadn’t had a war for seven years, which is a long time in military calendar terms. The two generals who run West Point, the commandant and superintendent, were driving down I-95 from West Point for a meeting. They stopped at one of those welcome centers where they have sit-down service, and they walk in and they’re wearing their uniforms. The hostess comes out and sees these distinguished looking men, and she smiles and says: Before I seat you, I just want to thank you for the wonderful work you do on behalf of the Parks Department. So they went to Jann Wenner and said they’d love for someone to come up and do a story.
Rumpus: I think there might be a parallel in the ascetic nature of a scheduled military life and the discipline you need with time while writing.
Lipsky: You know, that’s true about painters too. My mom is a painter, and one of the jokes I would tell people at West Point and after was like, you know, this didn’t feel all that unfamiliar to me. My mom has some very West Point ideas about keeping a schedule and doing a huge amount of work herself. I think for any job that includes a lot of training, things will end up regimented.
Rumpus: In On Writing, Stephen King talks about an author who would write for exactly three hours before work every morning [NB: I looked it up later–Anthony Trollope]. If he was in the middle of a sentence when he needed to leave, he stopped in the middle of the sentence. Was that the level of your mother’s schedule?
Lipsky: Well, if we were just sitting around she would get upset. Her home life ideal was that we would always be doing something that was enhancing or improving, which is kind of the idea when you’re training for the military. For me, it seems more like a thing about duration. I often will be, as a writer, pretty stupid when I sit down. The sort of thing that I would find is if you just stop writing after 2-3 hours and then if it hasn’t gone terribly well, you would sit down the next day with a bit of a sinking heart. There’s something really nice about going back and writing another five hours, and that’s where you push through. It’s a little bit like playing tennis. When the first fifteen minutes, half an hour, you’re aware of your stroke. Then as you play more you start hitting automatically. You might only get that after the first hours. You might only have it for the next half hour before the sweat becomes too thick on your forehead for you to see. But what you’re looking for is working all that extra time to get to that hour or two where you’re actually working without being encumbered by all the other thinking. There’s this great line in Updike: The room and I would warm up together.
Rumpus: Rushing to finish, to meet a deadline? A connection to your working at Rolling Stone?
Lipsky: I remember reading in a biography of James Joyce that Joyce began to work much more quickly on Ulysses in the last year when he already had a publisher. And there’s this lovely line in that the book: Joyce, working at the headlong pace that was more conducive to him than he was willing to admit. The fact that you have to wrap it up at a certain point can also be a great thing. I think that Wallace talks a lot in the book about how one of the bravest things he had done as a writer up to that point was to take a contract for Infinite Jest because he knew he would have to finish it.
Rumpus: In the book he says he wouldn’t do that again.
Lipsky: Yeah, but while writing it, he knew that whatever else was going on in his life, he had to get that book in by a certain day. He was a little bit late, and I remember he said he was very embarrassed about that. He didn’t realize at that point that most writers in the world are late. When Fitzgerald was having problems writing Tender is the Night, Hemingway wrote him a letter and said: Your problem is you keep trying to write masterpieces. All you can do is write as well as you can every day and know that because it’s yours it’s going to be really good and then come back and sit down the next day and keep writing really good stuff. So at the end you’ll have written a good book. Whereas if you try to write a masterpiece nothing will come at all.
Rumpus: Do you find yourself giving your students that same advice?
Lipsky: That is one of the things. You know: you’ve fought your way into an MFA program and you really want to show everything you can do. Sometimes it’s like you’re a cook and there’s a million dishes you could do, but if you try to serve them altogether at one seating it won’t go terribly well. Similarly, Wallace said what was hard for him when he was in his late twenties, was that he kept telling himself that he was this genius writer and so every sentence that comes from his pen should be genius. He had to quiet that down before he could begin writing the way he wanted. Sometimes you need a reminder that the writers you loved didn’t start out as the writers you loved. When I was in school I’d go to the card catalog, which is what you still had in the wood-and-papercut era before the internet, and look up Updike’s stories. I saw the New Yorker issues that he was in and went to the stacks and opened them up and what was really a nice surprise and a hard surprise too was how much the other stuff sounded like Updike. And then saying, “Ah, here’s his story, but these other sentences and paragraphs kind of feel like him too.” It’s sort of like if you love Lincoln you go and you visit the log cabin he’s from. And, as Nabokov in Lolita jokes: with period furniture, pretending it was his. Or you’ll go to Mount Vernon and see Washington’s house. When I love a writer I will go back and read their early books, but you’ll want to see what the stories looked like in the magazines they were from. When everything is still hope.
Rumpus: What are some recent books that have piqued your interest in that way?
Lipsky: Saunders. I love George Saunders, especially In Persuasion Nation. Also The Love Affairs of Nathaniel P by Adelle Waldman. It was just so smart moment by moment. There’s a scene when Nathaniel is at a restaurant with the girl that he loves. While he’s talking with her he notices that he doesn’t like the shape of her arm. He’s trying to follow what she’s saying and also thinking about his hamburger and the baseball game he can see over her shoulder, and there’s something wonderful about that. I also loved a brilliant book called Prep by Curtis Sittenfeld. The main character is someone who isn’t sure what her personality is, or whether she even has a personality, and sometimes when I teach that book I will teach it next to “Good Old Neon,” which is Wallace in a much more compressed way talking about a character with a similar problem. There are so many wonderful lovely things there, like the narrator is ending a relationship with the male lead in the book, and they’re never going to see each other again. He looks at her with the look of teenage boys, a look that’s kind of “predatory and tender.” And that’s such a brilliant thing to catch.
Rumpus: The things you’re describing are very zoomed in, small voice-driven moments. I remember you saying that’s what drew you to Wallace, his ability to capture the “brain voice” of people his age. Is that what you look for in good writing, mainly?
Lipsky: Yeah, what life sounds like inside. How we narrate to ourselves the impressions that come. Part of you is just you, and it’s almost separate from the part of you that walks around or is putting your hand on a stove and gaining the information that says it’s hot. Part of you is negotiating all the data. That part for me is someone kind of trying to make sense of what that experience is and is only spoken to by really great writing. It’s why we love writing. It says hello to us, and it’s one of the things Wallace talks about in the book as to why he has footnotes, he was trying to simulate the way you can have many simultaneous and branching thoughts at the same time. There’s a great moment in Lolita: Humbert has picked Dolores Haze up at summer camp, and he’s gotten her to the hotel The Enchanted Hunters and he’s tricked her into sharing a bed. It’s the moment his whole book has been leading towards. Humbert looks down at her “unfair amount of pillow.” And to have in the middle of this scene which is horrible and funny, to have him noticing at the same time that she’d also taken more of the pillow than someone sharing a bed should be entitled to take, that idea of having one thought you’re trying to focus on with another unwelcome bit of data you’re getting simultaneously. That’s what I’m reading for, those moments that kind of illuminate the strong surprising ways that we do perceive our lives.
Rumpus: When you’re teaching at NYU, how do you help your students get to that place?
Lipsky: Zadie Smith has a great essay called “That Crafty Feeling” and in it she says the only 24-karat gold-plated advice she has to give is this: step away from the vehicle. The best way to really see what you can do with a piece is to step away from the thing you’ve been driving. If you’ve worked on a story for two or three drafts and then you start a fourth draft, a last draft—unless you’re like George Saunders, who would have 296 drafts to go—you’ll still be the person who wrote it. Smith’s gold advice is if you put the piece down for a while, you’ll come back and see it different. You have to become, she says, both the reader and the writer of your own work. That’s a great position to be in; when you have a draft that’s mostly done, you can read in this magic position of being a reader who can make a sentence better as they’re driving through it.
Rumpus: Both you and Wallace got your names out there with shorter, nonfiction pieces. How should beginning writers today navigate between writing short pieces, sometimes unpaid, versus shutting themselves up in a room and working on a novel?
Lipsky: There’s a thing we did not have in graduate school, where agents will troop through NYU and talk about being an agent and how the book business works. We got that mostly by rumor. They will always talk about—just a sense that this is a simple brute thing—that novels always sell better than short story collections. That it’s an easier way. Wallace’s first was a novel, with lots of noise, and I think when his first collection came a few years later the relative quiet was puzzling. So that’s why it can be that if you feel a novel in you, it can be sometimes smarter to do the novel as your first thing, with stories to follow. On the other hand, Lorrie Moore, a great story writer, has written three novels and Saunders has never written a novel at all, but they have both been able to make careers really almost solely as short story writers and are two of the best writers in America now. With Wallace, the way he moved to doing pieces was that his last year at Amherst he wrote The Broom of the System as a thesis, which was then published while he was in the University of Arizona. He’d already started publishing some of the stories from Girl with the Curious Hair. And that gave him the chance to do journalism. He was a known quantity. After Girl came out and while he was writing Infinite Jest, his work was around and people could say, “Hey, do you want to go to the Illinois State Fair and write a piece about that?” When that went well, he could get the invitation to the cruise ship. And by then—because people knew his work—they weren’t looking for someone to do a piece, they were looking for him to do the thing they had read that he could do. In a lot of ways, even to do the kinds of pieces that are great work and good training, it can sometimes be better to have a book out. As a preserved audition for people to see what kind of stuff you can do well. There are some kinds of pieces you’ll do when just starting out that will be kind of expert exercises. They will show that you can do it, but not that only you can do it.
Rumpus: In the last ten years or so, you’ve stayed away from shorter pieces. Why do you think that is?
Lipsky: You keep finding out there’s more to say. Even the piece about David, at a certain point, I think the last long night and morning, he says he doesn’t know how I’m going to boil all this stuff down, because he knows that we’ve had a kind of great conversation, and how can you leave stuff from a great conversation out? He says so many great, cool, enlivening, things. It’s harder, like the West Point piece after the first year that I was up there, we had talked about going to 8,000 or 10,000 words, and there was just so much great stuff about the place. I was calling and saying I’m about 17,000 words in, I don’t think I’m going to pull this off. Bob Love, my editor, said: Just keep going. Don’t worry about the page count. Write what you have and then let’s work this out. There’s something great and which also feels true to our lived experience about that, something that’s long, something that’s 100 pages or 200 pages or 1,079 pages. Once you have a story that’s working, it leaves room for all the random things that are thrilling, or troubling, or confusing, or beautiful, about what happens to you inside when you’re on the phone with a former student or when you’re arguing with your girlfriend or reading or you’re walking with your dog. A million things, and what’s kind of weird about this is there’s the desire you have at any given moment for things to happen, whatever plot line your life features that month, but otherwise it’s slower and part of life is how you deal with that, in a way. The reason we get so excited reading is that it’s touching the place and way we spend most of our time, that narrative of desire and impatience and there’s really no other way to communicate that with other people. It’s why a writer like Salinger or Wallace can come along and be so thrilling. It what’s thrilling about The Corrections, that combination of gripe and want. It’s why readers rushed to embrace Lorrie Moore, because this private experience that’s the bulk of our lives, we’re hearing that captured, penned down, which is a wonderful thing.