After a prologue featuring David Lipsky hearing the news of David Foster Wallace's suicide in 2008, we flash back to 1996 for most of the duration, as the journalist travels to Wallace's home on the outskirts of Bloomington, Illinois for a few days before they head out to the final stop in Minneapolis, trying to pick his brain without being too pushy. The reserved author is very tight-lipped about things that are too personal in nature, which leads to a good deal of testiness on Wallace's part. Voids exist, as Lipsky begins to think that perhaps Wallace is trying to shape his image for the purpose of the interview and not be forthcoming about who he really is and what he believes, leading to some push back, and forcing the reporter to put together some insights based on the items Wallace keeps around his house.