A Supposedly Fun Thing I'll Never Do Again

The title itself tells you everything. A Supposedly Fun Thing I'll Never Do Again. Seven words that capture the central paradox running through David Foster Wallace's 1997 essay collection. Here is a book about things that are supposed to be enjoyable—television, vacations, state fairs, professional sports—but somehow aren't. Or rather, they are enjoyable, but in a hollow, unsettling way that leaves you feeling emptier than when you started.

Wallace wrote these seven essays over several years for magazines like Harper's, Premiere, and Tennis. The collection moves from personal memoir to cultural criticism to literary theory to celebrity profile. But every piece returns to the same diagnosis: American leisure and entertainment in the 1990s had become a machine that manufactured irony, alienation, and a strange kind of loneliness. The fun things we chase—the cruise, the TV show, the carnival ride—turn out to be cages wrapped in bright colors.

The book's title comes from its final and longest essay, an account of Wallace's seven-day luxury Caribbean cruise aboard a ship he renames the Nadir (meaning the lowest point). The essay opens with Wallace listing strange things he saw on the trip, then immediately undercuts any sense of wonder: "I will never go on a cruise again." The paradox is stated baldly. This was supposed to be fun. It was expensive, pampered, all-inclusive. And the author will never repeat it.

Wallace made his name as a novelist, but this collection established him as something rarer: a cultural diagnostician who used his own life as a case study. He was born in 1962 in Ithaca, New York, but grew up in Urbana, Illinois, the son of two university professors. He played competitive junior tennis, studied philosophy and English at Amherst, earned an MFA from the University of Arizona, and published his first novel, The Broom of the System, in 1987. But it was his 1996 novel Infinite Jest that made him famous—a sprawling, footnoted epic about addiction, entertainment, and a tennis academy that many critics saw as the definitive American novel of its era.

A Supposedly Fun Thing I'll Never Do Again was published a year after Infinite Jest, and the connections between the two books are everywhere. The themes are the same: the corrosive power of irony, the loneliness of the modern viewer, the way entertainment numbs rather than nourishes. The footnotes even grow longer and more digressive as the collection progresses, mirroring the style of the novel. This is Wallace working through his obsessions in real time, using magazine assignments as an excuse to examine the culture that produced him.

The opening essay, "Derivative Sport in Tornado Alley," looks back at his childhood tennis career. He wasn't a natural athlete, but he developed a defensive, mathematical style that exploited the terrible conditions of Midwestern courts—the wind, the uneven asphalt, the humidity. His strategy worked until puberty, when bigger, stronger opponents simply overpowered him. The essay ends with a tornado warning siren blaring as Wallace and his rival continue their rally, eventually blown into the net. Tennis, for the young Wallace, was a system he could control, a refuge from the chaos of the world. But control, he learned, was an illusion.

The second essay, "E Unibus Pluram: Television and U.S. Fiction," is the most theoretical piece in the collection. Wallace argues that television has created a culture of poisonous irony, where viewers watch others without being watched themselves, where commercials absorb criticism and turn it into more television, where the only acceptable stance is detached, knowing mockery. He invents a character called Joe Briefcase—the average American viewer, alone in his living room, consuming six hours of television a day. The essay ends with a call for a return to sincerity, for writers who dare to be "anti-rebels" and endorse "single-entendre principles." But Wallace admits he doesn't know how to get there.

The third essay, "Getting Away from Already Being Pretty Much Away from It All," finds Wallace returning to Illinois to cover the state fair. He arrives with a friend he calls "Native Companion," a woman who still lives in the Midwest, and together they wander through a landscape of fried food, livestock competitions, and carnival rides. Wallace feels like an anthropologist in his own homeland. The fair's strangeness—the clogging, the baton-twirling finals, the evangelical booths—fascinates and repels him. He realizes he no longer belongs here, but he doesn't belong anywhere else either. He's caught between two worlds, an outsider in every place.

The fourth essay, "Greatly Exaggerated," is a book review of H.L. Hix's Morte d'Author, a defense of the author against Post-structuralist critics who declared the author dead. Wallace argues that Hix's attempt to broaden the definition of "author" is so expansive that it destroys the very concept he's trying to save. "Hix destroys the author in order to save him," Wallace writes. The essay is short, academic, and reveals Wallace's own anxieties about how his work will be read.

The fifth essay, "David Lynch Keeps His Head," sends Wallace to the set of Lynch's 1996 film Lost Highway. He has almost no contact with Lynch himself—the director remains distant, smoking, directing with flattened affect. Instead, Wallace reflects on what makes Lynch's work so unsettling: the way it combines the macabre and the mundane, the way it implicates the audience in the sickness on screen, the way it refuses to offer moral comfort. Lynch's films, Wallace argues, are not just creepy for the sake of being creepy. They force viewers to confront their own complicity.

The sixth essay, "Tennis Player Michael Joyce's Professional Artistry as a Paradigm of Certain Stuff About Choice, Freedom, Discipline, Joy, Grotesquerie, and Human Completeness," profiles a 22-year-old professional tennis player who is the 79th best player on earth. Wallace watches Joyce play qualifying rounds at the Canadian Open and realizes that even the worst professional is leagues beyond anything he ever achieved. But the essay turns dark as Wallace examines what Joyce sacrificed to reach this level: a childhood of relentless practice, a father's ambition, the impossibility of any other life. Joyce is too good to quit but not good enough to be a star. His success is a gilded cage.

And then there's the title essay. Wallace boards the Nadir and descends into a week of manufactured bliss. The ship pampers him like a mother caring for an infant. The staff cleans his room with perfect, invisible timing. The food is endless. The activities are relentless. And Wallace finds himself spiraling into a strange psychological state—first guilt, then entitlement, then envy of another cruise ship he spots in the distance. He forces himself to participate in a full day of "Managed Fun," drinking too much coffee, ping-pong, skeet shooting, a hypnotist show. By the end, he's hollowed out, spending the final day in a glassy-eyed trance. The cruise was supposed to be the ultimate relaxation. Instead, it was a machine designed to replace genuine experience with pampered emptiness.

Throughout these essays, Wallace emerges as a character in his own right: awkward, hyper-intelligent, desperate for sincerity but trapped by his own analytical habits. He sees irony everywhere, even in his own attempts to escape it. He wants to connect with people but can't stop intellectualizing every interaction. He craves authentic experience but finds himself constantly observing, dissecting, turning life into material.

The question that haunts the collection is simple and devastating: What happens when the things that are supposed to make us happy don't? When the cruise ship, the television, the state fair, the professional sport—all the pleasures our culture offers—leave us feeling more alone than before? Wallace doesn't have an easy answer. But he insists that the first step is admitting the problem. That the hollow heart of American fun is real, and it's beating inside all of us.

What kind of writer would spend a week on a luxury cruise and come back with a 50-page essay about how awful it was? And what does that say about the rest of us, who might have actually enjoyed the trip?