One Writer's Road Trip with Novelist David Foster Wallace

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Gary Hannabarger / Corbis

David Foster Wallace

In 1996 Rolling Stone sent a young writer to cover David Foster Wallace on the last leg of his book tour promoting Infinite Jest. The gargantuan novel was climbing the bestseller list and Wallace was the toast of the literary world. In his new book, Although Of Course You End Up Becoming Yourself, David Lipsky gives readers full access to his conversations with Wallace as they chain-smoke in Denny's and try to catch a flight in Chicago during their five-day trek across the icy Midwest. Lipsky spoke to TIME about adopting a Midwestern accent and the difficulty of writing about such an enormous talent.

It's obvious now that Infinite Jest was a huge book and David was well on his way to becoming famous. But being involved in the literary world at that time, can you describe what the buzz was like?

It was like a microclimate. If you weren't a reader, you could have had a million thoughts. You could have been thinking about the Clinton re-election or you could have been thinking about [the fact] that Matlock was in its final season. But if you were a reader, it was like this climate followed you around for a whole year. Everywhere you went people were talking about Wallace. Sometimes when someone gets famous, there's a lot of bad feeling, but this was just excitement because he was so good. Although, talking to a friend of mine around that time, she said that all these relationships were being ruined by him. All the guys' girlfriends wanted to date him and all the guys wanted to be him, so it was causing all this trouble with all the [single] writers in New York. That's kind of what it was like, but the main thing was that it was exciting.

You were pretty young at the time. Was there any kind of anxiety or intimidation going into it?

Yes, because he was so smart. I didn't want to write the piece because he was going to read it. It was extremely unsettling. It's very different than interviewing a movie celebrity or a TV celebrity because they're famous for being charming or funny. It's like interviewing one of the X-Men; they have a talent they can use against you. David's skill is that he is brilliant and he can see things more clearly.

You guys seemed to get along really well, at least that's how it appeared in the book.

Yeah we started having fun. I think if you drive with anybody for 40 miles plus, you'll become friendly with them.

You mention a few times in the book that you started talking like him, started adopting his Midwestern accent.

I think when someone comes around who is that unprecedented, and that uncanny, that makes you sound the way you hope you sound. The way he writes is the way we flatter ourselves [thinking we would] sound if we just put the time in. At Rolling Stone that's the proposal they get every week. Let's do a David Foster Wallace take on X: the beverage convention, the NFL draft, the National Republican convention. But that also happens with speech, and when you are around someone who is thinking that powerfully, it's sort of magnetic. It was very funny to hear myself taking on those locutions.

Your conversations are all over the place; did you have a favorite topic to discuss with him?

I loved talking about Tarantino. I loved talking about writing with him; he said a great thing about what writers do. He said that if a writer does his job right, what he really does is remind the reader how smart the reader is and wake the reader up to stuff that the reader has noticed all along. For me it was those moments when he was just being funny. Like at the NPR station when that guy says, "We are going to record digitally," and David says, "So only yes or no answers." I can't think of anyone else who would be capable of making that joke.

After you left his house in Bloomington, did you maintain a relationship with him?

Never spoke to him again.

And the piece never ran?

What happened was I came back and I tried to write it, and it was impossible because I kept imagining him reading it. There's a great remark that Martin Amis made. He said that writing about books is the only thing in the world where you write about something in the format in which the performance was done. Like if you see Avatar, you don't shoot a Super-8 about how you felt about Avatar, or if you see a ballet, you don't dance out your feelings about Martha Graham. But when you are writing about someone who is a writer, its in their format, so you can't help but be less good. I was really unhappy about having to write it. I could visualize the reading chair he was going to be in. There had been a lot of heroin stuff with musicians in Seattle, so [Rolling Stone editor] Jann Wenner sent me to go live with heroin addicts for a month. When I came back, the [Wallace] moment had passed, and I didn't have to write it, which was a relief.

Did you ever consider writing the book differently, or was it always going to be presented as a straight transcript?

He said he was extremely unhappy with the idea of someone shaping the impression of him that's coming across and I thought, Look here is what he actually was like. If you would have asked me in August of 2008 who was the best writer, obviously it would have been David Wallace. If you had asked me who was the healthiest American writer, it would have also been him because he was warm and he could understand people and love them at the same time, which is a hard thing to do. He was just funny and alive and great and it seemed like that image — which is the image that you find in his books and which was the impression I had of being with him for five days — was being replaced by the image of this dark, unhappy person. It seemed like the best thing was to say, Here's what he was like to be with. Here's what he was like to be with in a car and on an airplane. It seemed like the only way to write about him.