In 2008, David Lipsky (Jesse Eisenberg) finds himself in a state of disbelief after receiving a call from Bob Levin (Ron Livingston). Levin informs him of an unconfirmed report about the tragic suicide of acclaimed author David Foster Wallace (Jason Segel). Lipsky, initially skeptical, searches online and is devastated to confirm the news. As tributes pour in for Wallace, Lipsky reluctantly reads a eulogy on his local radio station, attempting to process the loss of a man he had once interviewed.
While rummaging through some old cassette tapes, Lipsky is transported back to the days spent with Wallace twelve years earlier, when he conducted an in-depth interview with the enigmatic author known for his groundbreaking novel, Infinite Jest. At that time, Lipsky was experiencing moderate success with his own writing and was drawn to Wallace's brilliance after hearing a friend rave about his innovative works.
Eager to delve deeper into Wallace's world, Lipsky proposes to his boss at Rolling Stone, Levin, the idea of an exclusive interview with Wallace, asserting that he is a literary giant akin to Hemingway. After some deliberation, Levin greenlights the project, but warns Lipsky to ensure there’s a strong story to tell. Lipsky, excited about the journey ahead, prepares to meet the reclusive author.
Day One starts with Lipsky flying to Illinois, where he finds himself lost. A call to Wallace leads to an awkward exchange, revealing Wallace's discomfort with being contacted directly by fans. When Lipsky finally arrives at Wallace's home, he is greeted by the author and his two dogs, but their initial meeting is tinged with tension. Wallace insists on strict off-the-record rules for the conversation, wanting to protect his privacy.
As Lipsky accompanies Wallace to teach a class, he observes Wallace's unique teaching style, which resonates with students. Their dinner discussion reveals much about both men; Wallace candidly shares his thoughts on fame, relationships, and the struggles of being a widely recognized author. The conversation flows from the philosophical to the personal, touching on topics like addiction, loneliness, and the ephemeral nature of happiness.
On Day Two, Lipsky experiences a casual morning with Wallace, complete with a pop tart, and learns about Wallace's distinct style choices, such as wearing a bandana for comfort. They bond over thoughts about their audience, and the importance of authenticity in their work. However, the visit takes a darker turn when Lipsky gently probes into Wallace's experience with depression and his brief stay in a mental hospital, provoking Wallace to close off emotionally.
As the days unfold, their discussions navigate through the complexities of art, success, and personal demons. Day Five sees Lipsky witnessing a more cheerful Wallace as they share McDonald's together, leading to poignant exchanges about life and connection. Lipsky is left with a mix of admiration and melancholy as he reflects on the profound conversations they shared.
Ultimately, as Lipsky listens to the tapes in 2008, he is emotionally overwhelmed, realizing that the short time spent with Wallace profoundly affected him. He documents the conversations in a memoir, finding solace in the moments they shared, even as he grapples with the weight of Wallace’s untimely passing. In the end, Lipsky wishes he could convey to Wallace that their conversations had helped ease his own feelings of isolation, as he finally articulates, "being with him made him feel less alone."
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