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David Foster Wallace: The 'Fresh Air' Interview


This is FRESH AIR, I'm Terry Gross. The writer David Foster Wallace was suspicious of fame, other people's and his own, but he allowed Rolling Stone reporter David Lipsky to spend five days interviewing him and traveling with him in the final days of Wallace's 1996 book tour, promoting his novel "Infinite Jest." Those five days are the subject of the new film, "The End Of The Tour," starring Jason Segel as Wallace and Jesse Eisenberg as Lipsky. We're going to hear an interview I recorded with David Foster Wallace in 1997. In 2008, at the age of 46, he hanged himself. Looking back on his work, New York Times book critic Michiko Kakutani described Wallace as having used his prodigious gifts as a writer, his manic, exuberant prose, his ferocious powers of observation, his ability to fuse avant-garde techniques with old-fashioned moral seriousness, to create a series of strobe-lit portraits of a millennial America, overdosing on the drugs of entertainment and self-gratification. Before we hear what he had to say on FRESH AIR, let's listen to a clip from the film. This is shortly after Lipsky has arrived at Wallace's secluded in Bloomington, Ill. Lipsky has just turned on his tape recorder to begin the interview.


JASON SEGEL: (As David Foster Wallace) Listen, before we start putting stuff on tape, I need to ask you something. I need to know that anything that I say five minutes later not to put in, that you're not going to put in.

JESSE EISENBERG: (As David Lipsky) Absolutely.

SEGEL: (As David Foster Wallace) Just given my level of fatigue and my (expletive) quotient lately, it's the only way I can see doing it and not going crazy.

EISENBERG: (As David Lipsky) No, I completely understand.

SEGEL: (As David Foster Wallace) It's right back on.

EISENBERG: (As David Lipsky) You agreed to the interview.

GROSS: When I spoke with David Foster Wallace, his book, "Infinite Jest," had just been published in paperback, and he had a new collection of essays called "A Supposedly Fun Thing I'll Never Do Again" about the luxury cruise he was asked to write about for Harper's Magazine. The cruise ads promised exciting adventures and entertainment to fill every moment of the day. He wrote, it's as if they were trying to convince you that you are guaranteed of having a good time because the cruise personnel will micromanage every pleasure option, and your troublesome capacities for choice, error, regret, dissatisfaction and despair will be removed from the equation.


GROSS: Do you think that when people are on vacation, they worry that they're not making the right choice in what they're doing and they're not having as much fun as other people on vacation are having? And that when you have the day managed for you, you can just relax because the professionals are handling it for you (laughter)?

DAVID FOSTER WALLACE: I think that's probably true, and I think that there's a weird kind of paradox that the more expensive the vacation is, the more potentially anxiety-producing it is. And that's why I think that, you know, the paradox is that a great deal of the expense of a luxury cruise, other than the facilities, is the - this entire battalion of professional fun managers going around, and a big part of their job is to assure you that you're having a good time. And their smiles were very high-watt, and they were constantly sort of inviting people up to the microphone to give sort of almost evangelical testimony to what a good time they were having.

GROSS: You write, there's something about a mass-market luxury cruise that's unbearably sad. What's sad about it?

WALLACE: Oh boy, I think - now, again, I'm not any kind of cruisologist, right, so I'm just a regular sort of civilian who was on this thing. I think that I noticed the same kind of sadness whenever, in my own life, I know that there's hard stuff that I'm not dealing with. And so what happens is I'll jack it into fifth gear and begin moving so fast and doing so much and trying to experience so much that I'm really sort of trying to drown it out. What I really wanted, and Harper's didn't want to do it, was I really wanted to follow a couple cruisers back and see what the week after the cruise was like because the brochures and the sort of mythology of cruising suggests that you return to the stresses of your normal life, relaxed and refreshed. And, at least in my own experience, you know, the cruise was to completely infantilizing and there was so little demanded of me that even just, you know, standing in a supermarket checkout line seemed like an unendurable ordeal afterwards.

GROSS: You know, I really like the way you talk. You write about a pleasure and how difficult it can be (laughter) to really achieve. You write about pleasure in the "Infinite Jest," your latest novel. And I'm thinking, you know, one of the things relating to that, in "Infinite Jest," one of the characters finds that marijuana is - marijuana is no longer a pleasurable experience, it just makes him terribly self-conscious and therefore anxious. And I'm wondering what happens to you when you do something that's supposed to give you pleasure and it just makes you uncomfortable or anxious.

WALLACE: Boy, I'm not really even sure how to respond to that. Look, a lot of the impetus for writing "Infinite Jest" was just the fact that I was about 30 and I had a lot of friends who were about 30, and we'd all, you know, been grotesquely over-educated and privileged our whole lives and had better healthcare and more money than our parents did. And we were all extraordinarily sad. I think it has something to do with being raised in an era when really the ultimate value seems to be - I mean a successful life is - let's see, you make a lot of money and you have a really attractive spouse or you get infamous or famous in some way so that it's a life where you basically experience as much pleasure as possible, which ends up being sort of empty and low-calorie. But the reason I don't like talking about it discursively is it sounds very banal and cliche, you know, when you say it out loud that way. Believe it or not this was - this came as something of an epiphany to us at around age 30, sitting around, talking about why on earth we were so miserable when we'd been so lucky.

GROSS: Well, when did you realize that all the benefits you had in an educated middle-class life weren't bringing you happiness?

WALLACE: Well, look, I guess it sort of depends on what you mean by happiness. I mean, it's not like we were walking around fingering razor blades or anything like that. But it just sort of seems as if - we sort of knew how happy our parents were, and we would compare our lives with our parents and see that, at least on the surface or according to the criteria that the culture lays down for a successful, happy life, we were actually doing better than a lot of them were. And so why on earth were we so miserable? I don't think - you know, I don't mean to suggest that it was, you know, a state of constant clinical depression or that we all felt that we were supposed to be blissfully happy all the time. There was just - I have a very weird and amateur sense that an enormous part of, like, my generation and the generation right after mine is just an extremely sad, sort of lost generation, which when you think about the material comforts and the political freedoms that we enjoy, is just strange.

GROSS: In your novel, "Infinite Jest," you deal with the pursuit of entertainment and pleasure. In fact, "Infinite Jest" is the title of a movie within the novel. You want to tell us a little bit about that movie?

WALLACE: Well, the movie, I guess, is sort of the MacGuffin of the book. I guess the idea is a lot of the book is about a kind of art film director who eventually comes up with a film that's so entertaining that anybody who watches it never wants to do anything else. Then the interesting thing becomes, if such a thing exists, do you avail yourself of it or not, and various people wring their hands about various elements of that question, but that's part of what the book's about.

GROSS: Do you think there are other new forms of pleasure that people pursue in the novel?

WALLACE: Well, I think - and it's not much of a coincidence - I think a lot of the people in the book are at about, you know, the situation that I was in when I was starting to work on the book, which were people who not only were vaguely unhappy in certain ways, but they sensed a kind of incongruity about why they were unhappy and were beginning to wonder what values and assumptions were leading them to be unhappy and then facing the rather unpleasant fact that there's very little to replace those in this culture. If that makes any sense at all.

GROSS: What are the those that you're referring to?

WALLACE: Well, I guess the basic idea that - see, I feel lame saying it out loud, and it sounds like I'm Bill Bennett or something. I guess the basic idea that the purpose of life is to be happy or is to experience the most favorable ratio of pleasure to suffering or productivity to work or gratification to sacrifice or any of that stuff, which, you know, a couple generations ago, to say that kind of stuff would have made you, you know, a freak - a freak and an Epicurean - and now seems to be so much - simply an unquestioned assumption of the culture that we don't really even talk about it anymore. I'm certainly starting to perspire talking about it here...

GROSS: (Laughter).

WALLACE: ...'Cause I'm afraid it sounds very - you know, it sounds like I'm going to walk out of the room with my knuckles dragging on the ground.

GROSS: One of your essays in your new collection is about irony and how it's become the common language of TV and a lot of contemporary fiction. You talk about how television has institutionalized hip irony. Can I ask you to explain what you mean by that?

WALLACE: What sort of time limit is there?

GROSS: (Laughter).

WALLACE: No, I mean, the essay is really about the relation between TV and fiction and what it's like to be a fiction writer who watches a lot of TV. And I guess the basic point is that a lot of the tools that were used by literary fiction writers in, I guess, particularly the '60s, to help - I don't know if there was a social agenda. I think it was probably to debunk certain kind of hypocritical Ward Cleaver-ish assumptions that the culture was making about itself. Those techniques, including meta-discursive stuff, self-reference, irony, black humor, cynicism, grotesquerie and shock, that what's interesting now is - now that, really, television - I think it would be safe to say that television or televisual values rule the culture. Television is now successfully using a lot of those same techniques but using them for a very different agenda, which is to sort of create an ethos and please people and to sell products to consumers. So that - the essay is supposed to be a setup for sort of what is the literary rebel or the writer who wants to be engaged somehow with the culture do now? You know, how do you be a rebel when Burger King, you know, for two years their slogan was you got to break the rules? How do you rebel against anarchy or a kind of weird crafted anarchy?

GROSS: We're listening back to my 1997 interview with the late writer David Foster Wallace. We'll hear more after a break. This is FRESH AIR.


GROSS: This is FRESH AIR. Let's get back to the 1997 interview I recorded with writer David Foster Wallace. He's portrayed by Jason Segel in the new film "The End Of The Tour."


GROSS: You write about how irony can become not only tiresome but even tyrannical. What are some of the problems you see with the ironic voice, whether you're a viewer watching television or a writer using it in your fiction or essays?

WALLACE: Well, a vivid example to use right now is how I feel in here, answering some of the questions you are asking about pleasure. The beads of perspiration I get on my forehead talking about something like does my generation face a task in terms of exploring what values we want to live our lives by or what we think the purpose of our life is and how much is pleasure a part of it, I'm so terrified of sounding like Bill Bennett or a, you know, church lady who's been parodied on "Saturday Night Live" or, God forbid, Stuart Smalley, who's been parodied on "Saturday Night Live." That this entire how to talk straight about anything, that really means anything that might sound cliche, that might sound uncool, might sound unhip, I mean, there's an absolute terror that goes along with it. And I know, because most of my friends are my age and younger, that this is not just me, that there is some weird way that - if the greatest sin in the integrated in the past was, you know, obscenity or shock, the greatest sin now is appearing naive or old-fashioned so that somebody can give you a sort of a very cool arch smile and devastate you with one extraordinarily crafted line that puts kind of a hole in your pretentious balloon.

GROSS: Now does that - is that a problem for you as a writer? Do you feel that there are certain sentiments - certain, like, heartfelt sentiments that you're afraid to deal with because it might sound square and corny?

WALLACE: Well, it's more complicated than that because usually, if you're writing fiction, you're dealing with characters who, themselves, will have heartfelt sentiments but who, themselves, live in this culture right now and thus face all the impediments to sort of dealing with those parts of their lives that, you know, that we did. So it would be not only silly but unrealistic to have a character saying that kind of stuff. I don't know, I mean, other writers with whom I talk about this stuff, it's more just this - a lot of writers tired of doing kind of hip, slick, funny, dark, exploding hypocrisy, underlining once again the point that life is a farce and we're all in it for ourselves and that the point of life is to amass as much money/fame/sexual gratification, you know, whatever your personal thing is, and that everything else is just glitter or PR image - that we're tired of sort of doing that stuff over and over again. Yet to do stuff that flies in the face of that is to risk becoming the "Bridges Of Madison County" guy. I mean, a lot of the stuff that would seem on the surface of it to counteract that is gooey, hideous, horrible, retrograde, cynical stuff, if that makes any sense.

GROSS: Yeah, well, I think it's - I think it's just, like, very perceptive of you to put your finger on the limitations of, like, the need for irony but at the same time, the limitations of irony.

WALLACE: Irony, as far as I could see - and, you know, you can take college courses for three years on just what irony is, so there's something - I guess I'm going to assume that everybody kind of knows - when David Letterman comes out and draws himself up to his full height and says what a fine crows, you know, echoing the Arthur Godfrey of decades past, that's the kind of thing that I mean. Irony and sarcasm and all that stuff are fantastic for exploding hypocrisy and exposing what's wrong in extent values. As far as I can see, they're notably less good at erecting replacement values or coming any closer to the truth. And the thing about it is they're a terrific tool and they were used really well. We're just still using it, it seems to me, as a culture, 35, 40 years after it really had some use.

GROSS: Do you watch a lot of TV now?

WALLACE: I actually do not own a TV now but that is not TV's fault.


WALLACE: It's my fault because if I own it, I will watch it and, you know, even when, after an hour or so, I'm not even enjoying watching it because I'm feeling guilty at how nonproductive I'm being, except the feeling guilty then makes me anxious, which I want to soothe by distracting myself, so I'll watch the TV even more. And it just gets - I don't know, it just gets depressing. My own relationship to TV depresses me. It's not TV per se.

GROSS: When...

WALLACE: I do have a VCR, so it's not like I never watch a cathode ray screen.

GROSS: So when did you start realizing that in order to not watch TV you couldn't even own a TV?

WALLACE: I was sick in bed one day and decided I would amuse myself by drawing up a list of all the things I thought would be neat to read or that I should've read and that I had not read. By the time I was on the, like, 12th page, I began to panic and to realize that I needed to start doing some reading. And that if there was a TV in the room, I found out about a month later, I would simply - I mean, the game I'll play with myself is, oh, I'll read it with the TV on, which is just a farce. So I just decided I had too much to read to be able to own a TV.

GROSS: Something else you write about really well is self-consciousness. You write, for instance, about how writers are often bystanders, almost like voyeurs, and they're really good at watching other people, but they hate to be watched themselves and tend to be very self-conscious. Now, I know you don't want to overgeneralize and this isn't true of all writers, blah, blah, blah.

WALLACE: Well, I'm happy to overgeneralize.

GROSS: (Laughter) But it's certainly true of a lot of writers.


GROSS: And at the same time - I've said this before on FRESH AIR - I think self-conscious narrators make the best narrators because they're self-conscious about every detail, every action they're making and they're registering everybody else's action.

WALLACE: I do - I think there's a certain kind of neurological makeup that goes along with being a writer, and having been in the room with a few other writers at the same time, it's rather wearing to be around. And it does - there is a kind of hypervigilance about it. Unfortunately it's got disadvantages. If you turn that hypervigilance on yourself and, for instance, whether or not you have a pimple on the end of your nose, I mean, it can get really depressing. It can - it's also something of a continuum, and self-consciousness up to a point is really useful and really helpful, but I don't know how many people want to read a thing, you know, about self-consciousness, of self-consciousness or self-consciousness of that. And it - you can really kind of get in this infalling trap.

GROSS: One of the characters in "Infinite Jest" is a tennis player, and you were a champion tennis player when you were...

WALLACE: I was not. I deny.

GROSS: OK, not champion.

WALLACE: I deny steadfastly that I was a champion. I played competitive tennis on a regional junior level.

GROSS: You were...

WALLACE: I was not a champion. I don't want anybody from my hometown...


WALLACE: ...To hear me profess the word champion.

GROSS: You were a darned good tennis player (laughter).

WALLACE: I was decent by competitive standards.

GROSS: OK, good. And this is when you were about, what, age 12 to 15?

WALLACE: Something like that, yeah.

GROSS: Now did all your self-consciousness interfere with your performance on the court?

WALLACE: This is a marvelous set of - well, of course. I mean, this is - one of the great mysteries about athletes and why I think they appear dumb to some of us is that they seem to have this ability to turn off - I don't know how many of your listeners have this part in their brain - but what if I double fault on this point? Or what if I miss this free throw? Or what if I don't get this strike with the entire bowling team, you know, hanging - the professional athletes and great athletes, at first I thought it was that that stuff doesn't occur to them. But, you know, when I hung out with the pro tennis player for the tennis essay, it occurred to me that it's more like they have some sort of muscle that can cut that kind of thinking off. But that is literally paralyzing. You can end up like a bunny, you know, in the headlights of an oncoming car if you do that to yourself enough.

GROSS: Did you have that ability to turn it off?

WALLACE: No. And that is - I was middlingly-talented athlete but my big problem, and the coach told me at age 13, kid, you got a bad head. And what he meant was I would choke. I would begin thinking about, oh no, what if this happens and then I would say well, shut up, don't think about it. And then I would say to myself, but how can I not think about it if I'm not thinking about it. And meanwhile, you know, I'm standing, drooling, on the baseline going through this whole not very interesting game of mental ping-pong while the other guy is briskly going about the business of winning the match.

GROSS: David Foster Wallace, thank you very much for talking with.

WALLACE: Thank you, back.

GROSS: My interview with the late David Foster Wallace was recorded in 1997, one year after the new film about him is set. In the film, "The End Of The Tour," he's portrayed by Jason Segel. Jesse Eisenberg plays David Lipsky, the Rolling Stone journalist who accompanies Wallace on the end of his book tour, interviewing him every step of the way. Here they are at a diner.


SEGEL: (As David Foster Wallace) You know what I would love to do, man? I would love to do a profile on one of you guys who's doing a profile on me.

EISENBERG: (As David Lipsky) That is interesting.

SEGEL: (As David Foster Wallace) Is that too pomo and cute? I don't know.

EISENBERG: (As David Lipsky) Maybe for Rolling Stone.

SEGEL: (As David Foster Wallace) It would be interesting, though.

EISENBERG: (As David Lipsky) You think?

SEGEL: (As David Foster Wallace) I'm sorry, man.

EISENBERG: (As David Lipsky) What's wrong?

SEGEL: (As David Foster Wallace) It's just, you're going to go back to New York and, like, sit at your desk and shape this thing however you want. And that - I mean, to me, it's just extremely disturbing.

EISENBERG: (As David Lipsky) (Laughter) Why is it disturbing?

SEGEL: (As David Foster Wallace) 'Cause I think I would like to shape the impression of me that's coming across. Yeah, I don't even know if I like you yet. So nervous about whether you like me.

UNIDENTIFIED ACTOR: (As waiter) Here you go. Your food will be out soon. Can I get you anything else?

EISENBERG: (As David Lipsky) No, no, no, we're fine. Thank you.

SEGEL: (As David Foster Wallace) Thanks. What's this story about in your mind? What does Yom want?

EISENBERG: (As David Lipsky) Just what it's like to be the most talked about writer in the country or (laughter) that sort of thing.

GROSS: We'll hear my 2009 interview with Jason Segel after a break. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.