A Supposedly Fun Thing I’ll Never Do Again is a 1997 essay collection by David Foster Wallace. The seven essays explore 1990s US social issues through subjects such as television, tennis, and (in the most famous essay) a Caribbean cruise. The essays have been referenced many times in popular culture, particularly the title essay, which recounts Wallace’s experiences on a cruise.

This guide references the 1998 Abacus edition of the collection.

Summary

In the first essay, “Derivative Sport in Tornado Alley,” Wallace reflects on playing competitive junior tennis as a youth in Urbana, Illinois, when he discovered a talent for geometrically visualizing tennis court conditions and used it to his advantage. This tactic allowed him to execute a defensive style of play involving little more than returning volleys until his opponent made a mistake, became exhausted, or became frustrated. Wallace’s approach served him well until puberty, at which point he developed much slower physically than other boys his age. Before long, his defensive mathematical approach failed as bigger, stronger opponents simply overpowered him.

The next essay is titled “E Unibus Pluram: Television and U.S. Fiction.” The first phrase in this title is a play on the Latin phrase “E Pluribus Unum” (“out of many, one”), a US motto printed on the country’s currency. Foster’s version inverts the meaning, translating to “from one, many” (or “from some, more”). This essay offers one of the earliest expressions of Wallace’s “New Sincerity” ethos, an approach toward art and literature that the author is often credited with introducing. According to Wallace, the New Sincerity mentality dictates that artists abandon the irony and cynicism that became dominant during the Postmodernism era of the 1960s and that the author sees reflected in modern television: “The next literary ‘rebels’ in this country might well emerge as some weird bunch of anti-rebels, born oglers who dare somehow to back away from ironic watching, who have the childish gall actually to endorse and instantiate single-entendre principles” (81).

In “Getting Away From Already Being Pretty Much Away From It All,” Wallace details his experiences at the 1993 Illinois State Fair. He notes that the fair provided a microcosm of Illinois and Midwestern culture in general. People from rural and urban areas alike came to enjoy the activities, most of which centered on food. Wallace recalls sensing clear distinctions between agriculture professionals, event competitors, and the laypeople who simply wanted to go on carnival rides and indulge in unhealthy food.

In “Greatly Exaggerated,” Wallace reviews Morte d’Author: An Autopsy, a work of prose by US poet and literary critic H. L. Hix. In Wallace’s telling, Hix wished to preserve the idea of the author from Post-structuralist critics who sought to destroy it. Post-structuralism is a school of thought that deemphasizes the role of writers, rejecting the structures on which they rely, under the premise that readers can never truly know a writer’s intended meaning. Thus, post-structuralism shifts the emphasis onto readers, who inevitably process and perceive a text’s meaning in different ways.

“David Lynch Keeps His Head” describes how Wallace travels to the set of director David Lynch’s movie Lost Highway, on assignment for Premiere magazine, to interview Lynch. However, despite his press credentials, Wallace is afforded almost no contact with the director. In lieu of an interview, Wallace reflects on the impenetrably baffling plot of Lost Highway before recalling the mysterious and profound power of Lynch’s earlier films, particularly Blue Velvet. Citing a scene in which the protagonist watches from behind a closet door as one character sexually assaults another, Wallace argues that Lynch gets under audiences’ skin by implicating them in the deviant, sadistic behavior on screen.

In “Tennis Player Michael Joyce’s Professional Artistry as a Paradigm of Certain Stuff About Choice, Freedom, Discipline, Joy, Grotesquerie, and Human Completeness,” Wallace recounts attending the Canadian Open to watch US professional tennis player Michael Joyce compete. Reflecting on his commitment to the sport, Wallace wonders whether Joyce chose tennis or tennis chose him.

“A Supposedly Fun Thing I’ll Never Do Again,” describes Wallace’s experience on a seven-day luxury Caribbean cruise. As his fellow passengers engage in what they presumably consider fun and relaxing activities, Wallace is driven to introspection and despair. He likens the extreme pampering that passengers receive from the cruise’s hospitality staff to a mother caring for her infant’s every need. Wallace views this as evidence that, by going on a cruise, passengers express a desire to revert to a state of infancy. As the days pass, Wallace comes to take the luxury and pampering for granted, demanding more of it in hopes of fulfilling an adolescent impulse to want it all, despite knowing that the impulse can never be satisfied.