After the suicide of David Foster Wallace in September 2008, David Lipsky returned to the taped transcripts of an extended five-day interview he had conducted with Wallace while on the book tour that publicized the novel that made him a literary sensation, 1996's Infinite Jest. Initially intended to form the basis of an article for Rolling Stone, the project was eventually abandoned and the interview remained unpublished until now.

In Although of Course You End up Becoming Yourself, Lipsky takes the bold step of transcribing the tapes directly onto the page. Notes of surrounding noises and environments are often included (Wallace's dogs play a major role), although for the majority of the three hundred pages the only things present on the page are the voices of Wallace and Lipsky. What is the motive behind this formal gesture? Frankly, it is the same as the reason for the book's publication, and it is a sad one. Wallace's authorial voice, with its mixture of extraordinary erudition and occasional homespun folksiness, is one of the most distinctive in contemporary American writing and this undertaking represents a desire by Lipsky to capture the cadences of a personality now lost. Crucially, this conversational format is also significant in terms of Wallace's literary project, which has been frequently articulated – and the sentiment in this book is no exception – as a gesture against “loneliness.” Sincere and communicative dialogue is crucial in Wallace's fiction – and most nakedly dramatized in the eponymous sections of his 1999 collection Brief Interviews with Hideous Men – as a means of circumventing the prevailing cultural irony of the late twentieth and early twenty-first centuries and the solipsism that can result from the individual's extended exposure to such an environment. Lipsky's format, as well as providing a homage to this preoccupation, is a canny gesture in that it provides huge swathes of dialogue which allow breathing space simply unavailable to the general literary interview. As reader, we spend hours in the car with both men discussing the implications of fame and its ramifications for the individual's work ethic, the films of James Cameron (one longs for Wallace's take on Avatar) and the relationship of Wallace to his Mid-west home and his alienation from the New York-based literary establishment. The tentative relationship that emerges from these spare back-and-forths is all the more compelling for Wallace's continued suggestion of its contingency and Lipsky, despite his evident admiration for Wallace, never allows sycophancy to colour the dialogue or retrospectively suggest that this was an entirely cordial situation. The uneasiness peaks when Lipsky challenges Wallace on what he perceives as a calculated adoption of a persona for the interview: “We turn off the tape. He asks me to stop talking” (219).

Wallace's articulation of the importance of maintaining a personal shelter from what he calls “the fuss” about his work and his surprisingly candid discussions of his suicide attempt in the late 1980s lend a devastating weight to proceedings. Lipsky occasionally allows himself a bracketed aside within the text, a contemporary comment on the 1996 conversation, and the finely judged and heartfelt brevity of these interjections complements both the rhythm of the text and also the reader's unhappy understanding of where this road eventually led. However, he defiantly places his afterword at the beginning, allowing himself and the reader a victory, albeit a brief one, over time.