A Supposedly Fun Thing I'll Never Do Again

A Supposedly Fun Thing I’ll Never Do Again explores various types of alienation and detachment. In the opening essay, Wallace describes his childhood in the American Midwest. He played competitive junior tennis before he was no longer able to compete against his peers. This formative experience of junior tennis in the Midwest is a key part of Wallace’s identity; he still clings to his Illinois roots and his love of tennis when thinking of what it means to be David Foster Wallace. Over the ensuing essays, however, he explores the alienation he feels from these nostalgic childhood memories. The boy who played tennis beneath a tornado returns to Illinois to visit the state fair and, after years away, he feels like an outsider. The years spent playing tennis as a youth imbued Wallace with the idea that he was something of a competitive talent; however, watching the professionals at the Canadian Open up close, he realizes that he is extremely far from matching even a modicum of their talent. Wallace regarded himself as a Midwesterner and a tennis player but, as he grows older, feels alienated from these formative memories. He is detached from them in a meaningful sense and, through this process of alienation, loses his sense of self. His essays explore the idea of identity as his own identity begins to fragment.

Tellingly, Wallace devotes an entire essay to a fellow artist whose work explores these ideas of dissolving identities. David Lynch is the subject of one of the essays, as Wallace visits the set of Lost Highway, a film that concerns dueling, changing identities. Amid the Lynchian strangeness of the movie set, however, Wallace discovers a familiar concern. He repeatedly returns to the idea that Lynch’s work is misunderstood. Even the term Lynchian, he suggests, is broadly misunderstood. This bristling at the misunderstanding between audience and artist (and the lengths to which Wallace goes to try to correct his audience’s misinterpretations) reveals the extent to which he is beginning to feel alienated from his primary mode of expression. At the time of this essay, Wallace is a writer in the process of writing a complex novel concerning social alienation, and he feels increasingly detached from any hope that the audience might understand his work. He profiles Lynch and spends so much time addressing critical misinterpretation of Lynch’s work partly because of his own alienation from society. Wallace is desperate for his work to be understood, for his diagnoses of problems like alienation and detachment to correctly register with the public, so he devoted much attention to correcting the record on his peer’s artistic intentions.

The essay about the cruise is the longest in the collection and the most introspective examination of Wallace’s alienation. In this essay, he describes physically leaving his home country but doing so in the company of many traveling Americans. By leaving his country yet surrounding himself with its people, he feels even more alienated than ever before. Wherever he goes, even after physically detaching himself from other Americans and attempting to distinguish himself from his fellow passengers in the eyes of cruise ship employees, he cannot separate himself from his society. This prompts profound alienation, yet he cannot escape America. He is caught in a bind in which he feels detached from a society that traps him like a prisoner. This is the deep dilemma of Wallace’s alienation: Since alienation is a part of his psyche, his sense of self, he can never escape.