David Lipsky knew what he was up against with Although Of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace. To get to the good stuff, the witty interplay and deep philosophizing that constitute the bulk of his book, he’d have to acknowledge Wallace’s 2008 suicide and the shadow that kind of thing inevitably casts on the pages that follow. He breaks the ice with one tight, true sentence in the intro: “Suicide is such a powerful end, it reaches back and scrambles the beginning.” With Although, he’s asking you to peer past that end to a time when Wallace was in his prime, a happy-ish maverick rock star author coming into his own. The year was 1996. Lipsky was a Rolling Stone writer assigned to cross the Midwest with Wallace as he embarked on his first big book tour. The book, of course, was Infinite Jest, the avant-garde behemoth of a novel that was steamrolling the literary world at the time. Lipsky, now a respected author in his own right, returned home from interviewing Wallace only to have the magazine shelve the piece and re-deploy him to live with heroin addicts in Seattle for a month. So, until now, the two Davids ‘weeklong conversation — on writing, action movies, dogs, drugs, Alanis Morissette, etc. — was merely a Word doc in search of a printer. Now that it’s out there, Although, especially in audiobook form, feels like an essential piece of the David Foster Wallace puzzle. There are some things even suicide can’t scramble.
This book seems to go deeper than a straight-up biography could have. What made you decide on this all-conversation/no-filler format?
It seemed like the only way to. When I read a book by someone I care about, I’m curious about what they’re like. I wanna know how they experience the world. And it just seemed like with David, with any biography, you’d have to kind of fill in what he was like, what it was like to be with him. The thing that I love about him is how he experiences the world. He had this incredible ability to make me see the world more clearly.
I had read that week we spent together a bunch of times after I got back from Illinois. And it just seemed like the best way I could think of to give someone a sense of what he was actually like was just: “here, spend the time with him.” When I read it again after he died it seemed like the only way to get across what was so great about David personally.
So you get home, and a Rolling Stone transcriber turns your tapes into documents… And the bulk of this book was, essentially, just sitting in a hard drive for the last 15 years?
I kinda began working on the piece and then I got sent to Seattle to live with heroin addicts for a month and then when I came back it was too late to do the piece. So it was never written. But, you know, he’s my favorite writer. So I would go back every couple years and I would find the transcript again and would read it and see how much I had changed. Then I didn’t think about it for awhile. And then I was changing computers, I think in 2007, I read the whole thing again and it was just such an amazing thing to see what he’d been like. And the incredible excitement that he had about getting used to being a writer and…
Remember how he says in the book I know I’m a writer now? Throughout those five days, there was this exciting sense of someone who knew what their life was gonna be. And so to read that again 11 years after was also thrilling. Then a year later of course it was suddenly very sad.
As you say in the intro: Once you know a story ends in suicide, it’s hard not to go looking for signs of it earlier on.
Some people were afraid that he would just seem like someone who has always been kinda of headed toward suicide. And in fact he was this incredibly funny charming person, and that was what was most likely to be lost. So that was one of the things that was in the transcript and it made me really thrilled to do a book this way, saying, “Here’s what he actually was like. He was not a haunted figure. He was about the most charming person you could spend five days with. Spend them with him yourself, see what you think.”
You read Infinite Jest before heading out to spend all those days with the author. That book is a monster…
There are books about that book that are longer than most other books.
Were you worried he’d turn out to be a nut?
[Laughs.] No. I was worried that I would look stupid, you know?
I was nervous that he would find me not a good conversational partner. I didn’t think he’d be a nut, I just knew how warm he was from reading his work, so mostly I was mostly thrilled to be there.
If you love a writer, to suddenly be able to sit down and see their reading chair, to see their desk and to sit across the table at some noisy pizza place, and ask them anything you want, it’s just, it’s like a dream. It’s like this weird dream happening. It’s a lovely experience to have.
I would have been intimidated, meeting the reputed super-genius who’d written Infinite Jest. But, then we read in Although that Wallace was into Alanis Morissette. And the two of you go to see Broken Arrow. Not a lot of super-geniuses have conversations about a movie like that.
Or they wouldn’t be as illuminating. Yes. One reason I read biographies is to remind myself that Hemingway had off days. Or off years, or off decades. Or that Nabokov might sometimes not have been in a sunny mood.
And it was reassuring to me as a writer and also as a reader to remember things that David said like, “I know I’m not the smartest writer going but I work really really hard… I may not be that smart in conversation, but give me 24 hours alone and I can be really, really smart.” I teach in the graduate program at NYU. I would tell that to students and you could see how much it means to them.
Wallace was a former athlete, and he would talk about physical genius being dismissed as “easy” for those who have it. But, in fact, it’s all about the work.
You know, when you see someone play tennis as well as Sampras plays tennis, or as well as Federer plays tennis, you think “Oh, I’ll never have that.” But what you don’t see, of course, when you turn on TBS and you watch three hours of the U.S. Open, is the childhood spent from six to 18 where they’re hitting balls against the backboard, hitting balls to a coach, just hitting serve after serve.
I think people forget that’s what athletics are like. And they forget that writing is the same way. That it’s not gonna come easy. There’s someone who actually sits there and works as hard as they can to make the stuff that then seems effortless once we come home from Barnes and Noble and, you know, make ourselves some coffee and sit down and open it.
For him, there was a sweat equity to writing.
Thinking about Broken Arrow… I always laugh when I think about him watching a Jerry Lewis telethon all the way to see if he could do it. I thought it was so great to be able to talk about that. To just remind people that this guy was an incredibly, incredibly talented writer but he thought he was just someone who loved movies where stuff blows up. And he knew that the secret to his work was that he was willing to sit at his desk and work incredibly hard.
Writers, especially reporters, don’t like to waste time. Did it nag at you when you spent five days doing these interviews and didn’t get to write the piece?
Oh, I was so relieved. [Laughs.] I was utterly relieved. I had seen his reading chair so I knew exactly where he was gonna read it, and it wouldn’t have been as good as the profile he would have done of himself. So that was a horrible thing to think about.
And also: This is one of the great things about doing the book because he’s really trying. For whatever reason, in the second half of our trip he begins to really try very hard. He starts turning the tape on and off, while he tries to remember things and then tries to find the phrase that he wants.
And somewhere in there he ponders about how you’re going to reduce all the tapes to a magazine article.
The book is 300 pages. My transcript is about 255 pages. To read that and know I was going to have to boil it down to about four or five pages of a good profile in a magazine was just, in a way, very disappointing because it would lose everything. There would be some great quotes or whatever but you wouldn’t actually have his life there, and you wouldn’t have that great sense that I had had, of just what he was like to be around. Relief.
So you went from reading this massive tome about, among other things, addiction, and spending time with the author. And then off you go to Seattle to live with heroin addicts?
I had the eeriest feeling, for the four weeks I was in Seattle, of being in some part of Infinite Jest. Because one of the things he keeps saying about Americans is that we’re dying to give ourselves away to something. That we’re dying to be in some system, whether it’s a belief system like the recovery movement or whether it’s a system of self-improvement or of achievement like the tennis players at Enfield in Infinite Jest. The idea is that we’re dying just to have one thing that matters more than anything to us to order our day.
And it was wild. They were very nice people, the heroin people. I mean the dealer was a very nice guy and the people who I was spending all day with were nice, and they were smart. They just had this terrible hobby which had taken over their lives.
I remember I was at one guy’s apartment and he said, “This is awful but one nice thing that I’ve thought about is: It orders my day for me. I know every day that I have to make $120 to buy the heroin I need. I know every day that that’s going to be the big thing in my life. My life didn’t have that big narrative before and now every day it has that narrative. And that is something I enjoy in a creepy way.”
Were there glimpses of the depressive side when spent those days with DFW?
You had the exact same experience I had. You tell me.
Well, I can’t help but know now that in 1996 he had more issues than he was letting on.
That sounds right. But aside from that, when you’re listening to him talk, it sounded for him like depression was something that he had put behind himself.
If you had asked me who’s the most mentally healthy, emotionally healthy writer in America I would have named him because he found a great comedy in warmth. He didn’t seem like somebody who headed for suicide. He seemed like someone who was headed for a certain kind of warm, wry, really intelligent, and really productive and happy life. I was really really shocked actually when he died.
Had you had much contact after you left Illinois?
How would he view the book?
Relief that rather than the image being shaped, or whatever, it’s just him. I would hope that would be a relief. But of course there’s no way to know. It was this really wonderful accident in a way that the piece had never been written.
The phrase “David stops the tape” became a funny refrain in Although. He dealt with the interview in a very meta way.
[Laughs.] He wasn’t just being interviewed, he was trying to control the image of himself that came across.
Like you said, he’d liked to work at things…
Yeah. It gave him a chance to do another few drafts on what he wanted to say.
The book feels like a Richard Linklater film, in some ways. Not Slacker. Maybe Before Sunrise. It’s driven entirely by conversation, but somehow it works.
He feels really alive to me in the book. It would have been a really wonderful thing to be able to do it the way Linklater does in those movies, but, on the other hand, there’s that nice thing of being able to open the book up and see again what he was like when he was writing the stuff I really loved.