Summary

A Supposedly Fun Thing I'll Never Do Again is a collection of essays by David Foster Wallace, delving into his experiences with seemingly pleasurable activities like luxury cruises, state fairs, and high-stakes tennis tournaments. Through acutely observed details and Wallace's signature blend of humor and melancholy, he unveils the dark underbelly of leisure and entertainment in modern American culture. His experiences serve as a lens through which he dissects broader themes of consumerism, class, and the pursuit of happiness.

In "Derivative Sport in Tornado Alley," Wallace recounts his childhood as a near-great junior tennis player in the Midwest. He explores the unique challenges posed by the region's volatile weather, from blistering heat and oppressive humidity to relentless wind and the ever-present threat of tornadoes. He blends personal anecdotes with mathematical and geometric observations, examining how the environment shaped his game and his perception of the world. He details the intense rivalry with his childhood friend and tennis foe Gil Antitoi and their shared experiences with the sometimes destructive forces of nature and the challenges posed by competing in tournaments played in entirely different conditions. He also provides insights into his eventual disillusionment with the sport as his skills plateaued in the face of advanced facilities and technologies designed to eliminate the environmental challenges he'd learned to master.

In "E Unibus Pluram: Television and U.S. Fiction," Wallace tackles the pervasive influence of television on American culture and literature. He examines how television’s predatory voyeurism combined with the performative aspect of its actors and the illusions this creates for the viewer results in the viewers' belief that the performers are unaware they are being watched. He discusses the toxicity of this illusion and how this voyeurism leads fiction writers to confuse research with consumption and how these unrealities require serious complicity from the viewer. He then examines the complex relationship between television and its viewers, how we both mock and worship the medium. He explores how television's self-mocking irony and its manipulation of the tension between what we crave and what we think we ought to crave create a sense of solipsistic transcendence while reinforcing the very passivity and cynicism it inspires. He concludes with an examination of Image-Fiction as a response to TV culture and its limitations and proposes that true rebellion against the televisual might lie in sincerity and emotional depth.

In "Getting Away from Already Pretty Much Being Away from It All," Wallace describes his assignment to cover the Illinois State Fair for an East Coast magazine. He captures the sensory overload of the fair, from the sights and smells of livestock barns to the dizzying array of food booths and carnival rides. He observes the different "Us's" of the fair, from the agricultural professionals to the city dwellers to the carnies, highlighting the complex relationship between rural Midwesterners and their environment. He contrasts the Midwestern urge for communal spectacle with the East Coast desire to escape from stimuli, offering insights into regional differences in leisure and recreation. He also examines the underlying motivations and desires of fairgoers, reflecting on the nature of fun and the search for connection.

In "David Lynch Keeps His Head," Wallace profiles the enigmatic filmmaker David Lynch during the production of Lost Highway . He observes Lynch's peculiar habits and mannerisms on set, providing a glimpse into the director's creative process. He explores the themes of parallel identity crises, the disruption of time, and the blurring of reality and illusion in Lynch's work. He analyzes the recurring motifs of voyeurism, violence, and the grotesque in Lynch's films, while at the same time acknowledging Lynch's unique ability to capture the strange beauty of the mundane. He examines Lynch's unique position in the film world and the challenges he faces in balancing artistic integrity with commercial viability, offering insights into the nature of creative control and the pressures of the Hollywood system. He also assesses Lynch’s treatment of the subject of evil.

In "Tennis Player Michael Joyce's Professional Artistry as a Paradigm of Certain Stuff About Choice, Freedom, Limitation, Joy, Grotesquerie, and Human Completeness," Wallace follows the journey of Michael Joyce, a young American tennis player competing in the qualifying rounds of the Canadian Open. He details the grueling realities of the professional tennis circuit, contrasting the glamorous image of televised finals with the mundane challenges of travel, training, and competition. He analyzes Joyce's power-baseline game, exploring the technical and strategic intricacies of modern tennis. He reflects on the sacrifices required to achieve world-class athleticism, examining the narrow focus and intense dedication demanded by professional sports. He also ponders the nature of choice, talent, and the pursuit of excellence, considering the psychological toll of a life devoted to a single pursuit.

In the title essay, "A Supposedly Fun Thing I'll Never Do Again," Wallace chronicles his week-long luxury cruise through the Caribbean. With dark humor and sharp observation, he describes the overwhelming pampering, the contrived activities, and the unsettling atmosphere of forced fun. He dissects the cruise industry's marketing strategies, revealing the insidious ways in which they manipulate consumer desires and create the illusion of escape from the anxieties of everyday life. He examines the psychological dynamics of pleasure, desire, and dissatisfaction, reflecting on the nature of luxury and the insatiable cravings of the human heart. He also comments on his own reaction to the constant luxury, his guilt over the excess and his increasing disillusionment. Through these diverse subjects, Wallace examines how the promise of pleasure and escape often leads to feelings of unease, disappointment, and a heightened awareness of one’s own mortality.