Although of Course You End Up Becoming Yourself: A Road Trip With David Foster Wallace, by David Lipsky, Broadway Books (2010)
In the winter of 1996, Jann Wenner, the publisher of Rolling Stone, was flipping through the New York Times and landed on a photograph of David Foster Wallace. Infinite Jest, Wallace’s 1,079-page opus, had landed his name on bestseller lists and literati’s lips. He was a rock star on the rise, and he looked the part: Wallace sported long, stringy hair and three days worth of stubble, had a penchant for rumpled t-shirts and white bandanas, and often squinted at the camera. As David Lipsky put it, he looked like “someone who was going to invite you to play Hacky Sack, and if you refused, there was a possibility that he was going to beat you up.” The picture convinced Wenner. “He’s one of us. Send Lipsky.”
And so David Lipsky, then a 30-year-old fiction writer, set out towards Illinois to spend five days with Wallace on the last leg of the Infinite Jest tour, rolling through diners and hotels, missing airplanes, and filling up piles of cassette tapes with heartfelt discussions about literature and idle chatter about movies. Although of Course You End Up Becoming Yourself is a portrait of the artist as newly famous. It’s part biography, part road trip; we hear him at his most conceptual, expounding on his theories on writing, but also get a glimpse of him as a self-described “normal guy,” joking with waitresses and admitting to his infatuation with Alanis Morissette. Although of Course is essentially a raw transcription of Lipsky’s days with Wallace, complete with markers where each tape runs out.
Aside from an introduction, afterword, and some basic context for their conversations, Lipsky presents the marathon interview with little comment. He preserves every stumble and verbal tic in Wallace’s speech with obsessive devotion; Lipsky seems reluctant to edit out a single “um.” He does, however, make certain concessions for Wallace’s soft Midwestern accent, occasionally rendering “doesn’t” into “dudn’t” and “something” into “sumpin’” in a bit of vernacular styling less useful for its verisimilitude than distracting for its inconsistency.
Lipsky’s conservation of Wallace’s offhand remarks no doubt stems from his admiration of his work. “He was such a natural writer he could talk in prose,” Lipsky writes, “For me, this has the magic of watching a guy in a business suit, big headphones, step into a gym and sink 50 foul shots in a row.” This isn’t exactly true: Wallace doesn’t speak in the meticulously crafted, footnoted sentences of his Harper’s essays, but at work in his responses are the same qualities that make his writing so compelling. He answers Lipsky’s questions in an infectious mixture of academically precise terms and peppery slang. The gravitational pull of Wallace’s charm is on full display, as is his hyper-intelligence, electric sense of humor, and staggering self-awareness. Wallace comes off as both warm and generous, with a personality magnetic enough that Lipsky soon starts imitating his Midwestern accent despite himself. Wallace’s running monologue achieves dizzying heights of reflexivity, the product of an already self-conscious writer in a situation where his every remark is being repeated into a recorder. It’s a set of postmodern mental calisthenics Wallace is particularly adept at, neatly summarized in one of his remarks to Lipsky: “I don’t mind appearing in Rolling Stone, but I don’t want to appear in Rolling Stone as somebody who wants to be in Rolling Stone.”
Fortunately, Wallace is that rare magician who can explain how his tricks work without spoiling the illusion. Between swigs of Diet Pepsi, Styrofoam cups full of tobacco juice, dinging seatbelt reminders, and long, icy stretches of highway, Wallace narrates small portions of his life for Lipsky. They range from acquiring a taste for country music while teaching at Illinois State University (“They’re incredibly existential songs…they’re singing about something much more elemental being missing…than just, you know, some girl in tight jeans or something”) to his stint as a security guard (like “every bad 60s novel about meaningless authority”). Wallace also speaks at length, due to Lipsky’s prodding, about his struggle with mental illness, and his spell in suicide watch ("I knew that if anybody was fated to fuck up a suicide attempt it was me,” Wallace explains), passages that are almost unbearably heart-wrenching in light of his 2008 suicide.
If you aren’t already a member of the Wallace fan club, Lipsky’s gnarled transcription won’t necessarily compel you to join. But if you’re already a DFW acolyte, the incomplete biography that Lipsky slowly cobbles together is a small but illuminating window into Wallace’s well-guarded personal life and an intriguing look at the mid-1990s literary scene. “Books are in some sense a social substitute,” Lipsky writes, “You read people who, at one level, you’d like to hang out with.” Although of Course offers a glimpse of Wallace in his prime for those of us who weren’t lucky enough to know him outside of his books.