In 1996, David Foster Wallace's novel Infinite Jest was released to a wave of publicity unlike anything the world of publishing had seen since The Bonfire of the Vanities. Reviews were not entirely positive, but there were two things on which critics agreed: nobody had ever seen anything like it, and Wallace was the first writer to capture the voice of his generation in a serious literary novel. Rolling Stone magazine sent David Lipsky to the Midwest to follow Wallace on the last leg of his book tour, and, over the course of a short flight and two long car rides, Lipsky and Wallace discussed how he wrote Infinite Jest, Wallace's influences, literature, film and film criticism, writing and how it is taught, Alanis Morisette, Quentin Tarantino, and basically everything else that you would expect two highly educated thirty-something-in-1996 literary types to discuss. Lipsky left Illinois with a bag full of audio cassettes that would, once transcribed, fill more than 300 pages. It is an interesting conversation, like My Dinner With Andre for America's Generation X.
Wallace and Lipsky discuss several of Wallace's familiar themes - how it is impossible to escape the media in modern society. These roughly break down into 'subject matter' themes: tennis, illegal drugs, addiction, alienation, the corrosive effects of television, mental health and pharmapsychology (among others). and 'big picture' themes, such as the need for sincerity and empathy, the importance of identifying cliches and refusing to be manipulated by them; how consuming serious art makes us better people, and a general, reader-friendly sense that literature can't be written exclusively for other writers and graduate students, it has to reach readers where they live.
During my senior year in college, I was assigned to read Wallace's story "The Depressed Person" for an English course on post-World War II American literature. "The Depressed Person", one of Wallace's earliest short stories, is told in the first person, and about a depressed young woman whose inability to talk about anything other than her own depression annoys, and, eventually, turns off, everybody who is important in her life. The story is experimental, and meant to annoy and depress its readers. Because it the story is so effective, it is also very annoying. In my small-group discussion section, I remember saying that I thought the story was well-written, but that, if I was a person in the real world, who worked all day and came home at night and read to relax, that I would, despite my admiration for the author's skill, find this story to be enormously depressing and aggravating. The near-universal reaction from the rest of the section was: but you don't understand. David Foster Wallace is a genius. The story is meant to annoy you. The fact that it annoys you is just proof of Wallace's brilliance. I said that I fully understood that it was meant to annoy me, but that a well-executed story that is meant to annoy me isn't as enjoyable as a well-executed story written with any number of other goals in mind. Some of my classmates regarded me as if I was a philistine; to them, at least at that point in their lives, their appreciation for Wallace's skill as a stylist trumped all else.
After listening to some mid-00's interviews Wallace gave to NPR and Charlie Rose, and after reading his widely-disseminated Kenyon College commencement address, and now after reading Although You End Up Becoming Yourself, I feel somewhat vindicated - I doubt that Wallace himself would have agreed with my former classmates who defended his early writing so fiercely. In his forties, Wallace seemed to focus more and more on our culture's increasing levels of narcissism, and struggled publicly with what it means to live well without inconveniencing those around you. Wallace began to distance himself from his highly experimental earlier works, because he believed that serious reading should make us better people, and that stories written to show off to other writers, or to impress the reader, rather than challenge and entertain, weren't worth the time that busy people who work for a living have to invest to read them. Wallace believed that a lot of his early writings, including his first novel, The Broom of the System, some of his early short stories, and even the title essay of his best-selling essay collection A Supposedly Fun Thing I'll Never Do Again, which he, in hindsight, saw as being overly critical and snarky. A Supposedly Fun Thing is one of my favorite books, but I don't disagree with Wallace about his early fiction - it is much easier to appreciate for its technical accomplishment than it is to love, or even enjoy on a gut level. If Wallace was so disgusted by the ceaseless barrage of irony that he encountered whenever he turned on the television, how come his own writing could be brutally cutting and sarcastic? What to make of the fact that Infinite Jest can be read to be sincere on the big issues, while consisting of a thousand small-scale ironies? How is one supposed to interpret the parts of his interview where he shares what purports to be his love-one-another philosophy, then admits that he knows what he just said "sounds like a piety," then writes short stories in which a great team of painful humor is had at his characters' expense? Is it just that Wallace had identified a problem, but was unable to come up with a solution? If that's true, couldn't one argue that he nonetheless came closer than anybody else could have? I don't know how to answer these questions, but it bothers me they do not seem to occur to a lot of the young readers who worship Wallace so sycophantically.
Although You End Up Becoming Yourself captures Wallace at what I would call the "end of the beginning" of his career (this is a difficult point to demarcate, because several books that would not be released until after these interviews had already been written/were still in the pipeline). I don't necessarily prefer late Wallace to early (pre-Infinite Jest) Wallace, but I believe that Wallace preferred late Wallace to early Wallace, even though 'late Wallace' eventually killed himself. His death was a great loss, and also sort ironic, in that somebody who was so fascinated with the day-to-day living of life would, due to crippling depression, hang himself in his mid-forties. And if you want to try to resolve that contradiction, I wish you so much more than luck.