John Hockenberry: David Lipsky, this is kind of a dream come true. In a way you’re sitting down with a writer who you obviously admire, you’re spending time with him, is it also a way of vanishing into his work by sitting down with him?

David Lipsky: Well, yeah, cause one of the great things about, both about being with him and then reading the book afterwards is it’s like being in an essay he’s doing live, it’s like being in his great narrative voice as he’s gong into a restaurant, as he’s going through an airport, as he’s going through the mall of America.  So it was as if you woke up inside one of David’s paragraphs.

John Hockenberry: And were you comfortable on this trip with him?

David Lipsky: In the beginning, he doesn’t - I have the impression he doesn’t like me, and I get that impression because he turns to me in a pizza restaurant and says “I’m not sure if you are a very nice man or not.”  But, yeah, then afterwards as we started driving around more, yeah. 

John Hockenberry: There was a sense of, in some of the recordings you made, and to hear David Foster Wallace’s voice right now is… y’know quite extraordinary, here’s him talking with you, on this road trip back in 1996, with every bit of the whimsy you would find on the page.

[AUDIO David Foster Wallace: I have this… here’s this thing where it’s going to sound sappy to you, I have this unbelievably, like, 5-year old’s belief that art is just absolutely magic, and that good art can do things that nothing else in the solar system can do. END AUDIO]

Hockenberry: Can you see his face, when he was saying that to you?

David Lipsky: Yeah, with a little small smile, and also like, I’m so glad that you guys used that quote because it’s one of the things I think about when I pick up… that’s kinda how that thing you said about whether it was kind of like being in a dream, it’s like when you wake up from it. When I pick up books now I think about things, I hear different things he said and I’ll hear that kind of quote, like, about art being magic and um, so it’s more.. I tend to see it more as words on the page because that’s how I know him best as a writer.

John Hockenberry: He seems very vulnerable there, he says it’s a five year old’s notion to think of art as being absolutely magic, but in fact many, many artists believe that, he just retains this childlike vulnerability about what it is he’s doing.

David Lipsky: Yeah, it’s also like you may need that five year old sense of magic to then go through the decades and decades that you need afterwards to create the magic yourself.

John Hockenberry: Well, let me just give you a sense of some of the gems, I mean you can oren up to any page in Infinite Jest but this is on page 533, this is a typical scene, David Foster Wallace at his best. 

“Each of the women’s legs was shorter than the other.  How can a leg that is shorter than the other leg can have the other leg shorter than it?” .... "I’m also in another fellowship, almost four years in, the UHID, the Union of the Hideously and Improbably Deformed.  The veil is a sort of fellowship comparison." 

“If you don’t mind me asking, how come you’re in it?  UHID?  How are you supposed to be deformed? It’s nothing that sticks way out if I can say it, are you missing something?”

A kind of, pure ludicrousness, but an intimacy at the same time.  Did you, in a way, as a writer, were you jealous of him, having the ability to come up with stuff like that?

David Lipsky: When you come across a great writer, yeah for better or worse you’re a little jealous. Cause it’s like if you’r eplaying NBA ball and you’re thinking ‘yeah I’m six-foot-four, six-foot-five, I have a pretty good percentage on my jump shot’ and then some guy shows up who’s eight feet tall and can dunk without jumping. But then there’s the great thing, as you know, as a writer and as a reader which is, someone who’s writing that well and in that new a way is showing you ways that you could do things too, so you become immediately grateful. 

John Hockenberry: David Lipsky is a contributing editor at Rolling Stone and author of the new book “Although of Course you End Up Becoming Yourself – A Road Trip With David Foster Wallace.”  Also with us is Amy Wallace-Havens, sister of David Foster Wallace.  Good morning Amy.

Amy Wallace-Havens:  Good morning.

John Hockenberry: So, what’s it like to hear your late brother’s voice speaking so much with that whimsical sense of vulnerability you get in his writing.

Amy Wallace-Havens: Well, it’s very strange, I think even if I wasn’t lucky enough to have access to so many recordings of his voice, his voice was a very pleasant voice and very, very memorable to me, and he always spoke with a sort of sense of wonder of exasperation about almost anything.

John Hockenberry: And growing up with your brother must’ve been like being on a road trip with an amazing writer.

Amy Wallace-Havens: We didn’t travel in cars well together really.  But yeah, I mean, it was never boring, when we were kids we had a fairly intense sibling rivalry, but as we got older we became very close, and he was just an exceptionally good brother.

John Hockenberry: And certainly a brilliant writer, but someone who was capable even back in 1996 of talking about his sort of vulnerabilities and depression, which really sort of dogged him throughout his career.  David Lipsky what was going on when David Foster Wallace told you this story, and let’s listen to the story first.

[AUDIO David Foster Wallace: I’ve decided that I really need to find a few things that I believe in,in order to stay alive, and one of them is that… that I’m extraordinarily lucky to be able to do this kind of work, and that long with that luck comes a tremendous obligation to do the best… to do the very best I can, that doesn’t make me a great person, it just makes me person that’s really exhausted a couple other ways to live, y’know and really taken them to their conclusion, which for me was a pink room with no furniture and a drain in the center floor, which is where they put me for an entire day when they thought I was going to kill myself, where you don’t have anything on and somebody’s observing you through a slot in the wall, and when that happens to you, you get tremendously… unprecedently willing to exist, to find alternatives of how to live. END AUDIO]

John Hockenberry: A casual, rollicking discussion of a very intense moment of depression, David Lipsky?

David Lipsky: We were driving and he was talking about, in a way, how he had become the writer who could write "Infinite Jest."  He had, when he was younger, he had cared a great deal about how his writing would be received and how it would be read.  That was part of what had put him in that room.  I love that when he’s telling that story that he also then takes it a little bit farther and makes it funny and laughs.  That’s what great about him as a person and as a writer, he’s totally alive to data, and he is kind of making it his own, he’s finding the real live thing that’s funny in it.  What he’s talking about is, after that time when he went into McClain Hospital, he kid of burned of a lot of other things he’d been writing for and then he came out and spent the three years writing "Infinite Jest" and he said that he’d been protecting himself before that by always writing at three-quarters speed the way you would if you had a paper due, like you write the night before and then if you get a semi-good grade you’re like “okay, if I worked a little harder.”  And he said it was just gonna say “screw it”, he was just going to write as well as he could on this particular book, and if it couldn’t get published, if people didn’t like it, at least he would know that he had worked as hard as he possibly could and he felt that now he was a writer.

John Hockenberry: Amy Wallace-Havens, listening to your brother’s voice there, it seems that he’s got it under control, that he’s had the difficulty, that he understands the vulnerability inside him, but with that laughter, it really feels like he has it beat.  Did you feel that way?

Amy Wallace-Havens: Well, I think that he sounds very jaunty there, as if this is something he’s done some thinking about and has conquered and has moved away from, and I think at that time, he was feeling very good.  He was on medication that was taking care of the stuff that was so dangerous to him physically and emotionally, and of course he was so relieved and so happy that he’d finished this book and that somebody had published it and that obviously at least a few people were reading it… that was a big fear of his, that it was going to be so long and so weird, and so much access to his head that it would sort of repel people.

John Hockenberry: Although you could almost say those were the blurbs.  “Long, weird and access to my head, two thumbs up.”  That’s kind of what the reviews were, it was an amazing moment back then in 1996.  I’m wondering, David Lipsky, if this road trip was kind of a disillusionment, that in a sense, we may yearn to go on road trips with the writers we admire, but when we do, they lave the page and become something fundamentally different and unrecognizable. 

David Lipsky: I think that’d be true if it wasn’t a road trip with David.  To me, he was so much the person I’d known as a reader, it was like a re-illusioning, and I mean, I’d been reading the book a lot because I’ve been talking about the book a lot since it came out and just, just to be back in the car with him and to be- I mean it’s the voice, it’s the voice of those essays, it’s the sense of being around this incredibly kind, incredibly funny, incredibly brilliant person is just the sense I get from reading him, so almost a double re-illusioning.

John Hockenberry: Although at a certain point he’d just about had it with you, right? 

David Lipsky: Well, I think at a few points he’d had it with me, I’d say there were two or three points throughout, I think by the end he was certainly ready for me to pack up and go and I kept on making up excuses to hang around.  But I think he was ready for me to go by the middle, and once we went into extra innings or whatever, he just gently nudged me out.

John Hockenberry: Amy, do you think in the end the magic that he so believed in about his art abandoned him, and he ended up taking his own life? 

Amy Wallace-Havens: That’s a hard question.  I don’t think he was believing in magic much the summer of 2008, I think that he was trying to strike a balance between the writing life, which is necessarily a fairly solitary one, and a family life.  He had a wonderful wife, Karen, and he really loved spending time with her, and one of the reasons he went off of the medication, there were some scary physical side-effects that were starting to manifest, but also, just, he’d felt good for a long time, the medication sort of bloated him a little bit, made him just a little bit irritable.  Although, over the years we’d lost track of that we’d thought that was just David but it was actually part of the medication and so on the one hand he was feeling really good, he felt like a real adult, which he spent a lot of his life trying to figure out exactly what that meant, and trying to get everybody else to think about that, and ultimately, when he tried to reconcile the two, unfortunately because there was a medication that was so crucial to the crux of those things that failed, it couldn’t work.  He had no sense of magic or of hope, the last three months of his life. 

John Hockenberry: And certainly, the end of his life is a sobering portrait of the power of depression to even conquer a talent as formidable as David Foster Wallace.  Amy Wallace-Havens, sister of the late David Foster Wallace, thanks so much for being with us. 

Amy Wallace-Havens: You’re welcome. 

John Hockenberry: And David Lipsky, contributing editor at Rolling Stone and author of the new book “Although, of Course, You End Up Becoming Yourself – A Road Trip With David Foster Wallace”.  A chronicle of those moments you spent with David back in 1996, let’s leave everyone with this last sort of sense of what he imagined for himself going forward.

[AUDIO David Foster Wallace: I wouldn’t be so careful about this kind of stuff if I felt very much confidence that I could handle it well.  And I’m aware this makes very good copy and this’ll be a neat part of the article, but it’s also really like, I feel like we’ve sort of become friends… understand that, this stuff is really scary.  And I think if we were in exactly the opposite situation, you’d be saying a lot of the same stuff.  It’s great, but it’s also really scary at the same time, because I’ve got what I hope is like 40 more years of work ahead of me… AUDIO END]

John Hockenberry: David Foster Wallace speaking in 1996.  David Lipsky, you want to say something to your friend before we go?

David Lipsky: To.. to um?

John Hockenberry: David. Anything you didn’t say?

David Lipsky: There’s a great thing that John Franzen said when he was with David about six weeks before David died, he said that “I felt grateful to him for letting me be there.”  And that’s how I felt, getting to spend those five days with David, so thank you.

John Hockenberry: Thank you David Lipsky.