JAm It! (Journal of American Studies in Italy), N. 10 (2025): Resurgence and Decolonization: Creating Alternative Worlds

The overreaching argument of Paolo Pitari’s book is that David Foster Wallace ultimately failed in his aspiration to write a kind of fiction that would meaningfully deal with and “redeem despair” (1) in US society. This idea is suggested right from the outset in the book’s title that characterizes free will as a “problem” in the novelist’s oeuvre. Pitari suggests that this existentialist contradiction throughout Wallace’s work stems from the fact that he found himself at a fork in the road, seeking to reconcile the meaningfulness of life with free will. Observing that such an attempt, whether in philosophy or fiction, is inevitably doomed to fail, the author posits that Wallace’s works, precisely because of their insightful failure, encourage us to reconsider our interpretation of the world as one that inherently entails despair.