A Supposedly Fun Thing I'll Never Do Again

Content Warning: This section of the guide mentions death by suicide.

Born on February 21, 1962, in Ithaca, New York, David Foster Wallace was a vital figure in contemporary US literature. He was raised in a household steeped in academia. Both his parents were professors at the University of Illinois, where he spent much of his childhood. As he describes in his collection of essays, A Supposedly Fun Thing I’ll Never Do Again, Wallace was a talented junior tennis player. As he notes in the essay “Derivative Sport in Tornado Alley,” however, he was unable to maintain his athletic prowess into his later teen years.

As a young man, Wallace attended Amherst College, where he pursued a double major in English and philosophy. During this time he began to hone his craft as a writer, experimenting with different styles and forms of expression. After graduating from Amherst, Wallace studied creative writing at the University of Arizona, where he earned a master of fine arts degree in 1987 (as he notes in the essay “E Unibus Pluram: Television and U.S. Fiction”).

Wallace burst onto the literary scene in 1987 with the publication of his debut novel, The Broom of the System. A sprawling, ambitious work, it showcased Wallace’s talent and established him as a notable writer. The novel, set in a surreal alternate reality, explored themes of language, identity, and the nature of reality. Wallace further examined these themes in later works, including novels and essays. Despite the critical acclaim he received for The Broom of the System, Wallace struggled to find his footing in the literary world. He spent several years teaching at various universities and working odd jobs to make ends meet, all the while grappling with bouts of depression and self-doubt.

Not until the publication of his essay collection, A Supposedly Fun Thing I’ll Never Do Again, in 1997 did Wallace finally began to receive the recognition he deserved. The collection, which featured essays on a wide range of topics, from tennis to cruise ships to the Illinois State Fair, showcases Wallace’s wit, keen observational skills, and uncanny ability to dissect the absurdities of modern life. Throughout the book, Wallace hints at the ideas and theories that inform his later and most famous novel, Infinite Jest (1996). Like the essays, Infinite Jest is a sprawling, encyclopedic work that defies easy categorization. At its heart, it is a meditation on addiction, entertainment, and the search for meaning in a world that seems increasingly devoid of it.

A central theme in Infinite Jest is the idea of entertainment as a form of escapism, a way for people to numb themselves to the pain and emptiness of their lives. Wallace explores this theme in depth in the essay “E Unibus Pluram: Television and U.S. Fiction” through detailed dissection of the interplay between vacuous irony and mass media, as well as in the title essay, which reflects on the ways that cruise ship passengers use entertainment to distract themselves from their inner turmoil. In addition, the collection makes extensive use of footnotes, which becomes increasingly common throughout the chronologically ordered essays.

While A Supposedly Fun Thing I’ll Never Do Again is filled with moments of humor and absurdity, Infinite Jest delves deeper into the darker recesses of the human psyche. The novel is populated by a sprawling cast of characters, each fighting their own demons and struggling to find meaning in a world that often seems indifferent to their suffering, whereas most of the essays in Wallace’s collection feature him (or his viewpoint) as the primary protagonist or narrator.

The essay collection provides biographical and ideological insight into the novel. At the heart of Infinite Jest is the Enfield Tennis Academy, a prestigious boarding school where the novel’s protagonist, Hal Incandenza, and his classmates struggle with addiction, identity, and the nature of reality itself. The parallels between the tennis academy and the luxury cruise ship in A Supposedly Fun Thing I’ll Never Do Again are striking, both serving as microcosms of a society that is obsessed with pleasure and entertainment at the expense of everything else. In particular, the novel describes a yearning for a form of social sincerity and integrity that, throughout the collection of essays, Wallace suggests has been sapped from society. While his essays and his fiction both portray irony as a dominant part of modern existence, Wallace constantly strives to push back against the inherently nihilistic idea of a culture built on nothing but irony and jaded detachment.

Wallace’s struggles with depression ultimately cost him his life. On September 12, 2008, at age 46, he died by suicide, leaving behind a body of work that continues to resonate with readers. In the years since his death, Wallace’s reputation has grown. His novels, essays, and short stories are studied in universities around the world, and his influence is evident in the work of countless writers who followed in his footsteps. An unfinished novel, titled The Pale King, was published posthumously in 2011 using files and manuscripts prepared by Wallace for his widow at the time of his death. The novel was praised by critics.