Editors Reads
A Supposedly Fun Thing I'll Never Do Again by David Foster Wallace — book cover
intermediate

A Supposedly Fun Thing I'll Never Do Again

by David Foster Wallace · Back Bay Books · 368 pages ·

4.3
Reviewed by Marcus Webb

Wallace's first essay collection includes his piece on the Illinois State Fair, an extended essay on David Lynch, 'E Unibus Pluram' on television and American fiction, and the title essay on a Caribbean cruise — the funniest and most formally inventive piece of literary journalism of the 1990s.

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Editors Reads Verdict

The collection that established Wallace as the most technically inventive journalist of his generation, and the one in which his central argument — that irony had become the default American mode and that fiction needed to find a way past it — received its fullest early expression.

4.3
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What We Loved

  • The title essay is one of the funniest long-form pieces of nonfiction published in the 1990s — formally inventive and emotionally honest simultaneously
  • 'E Unibus Pluram' is the essential document for understanding Wallace's critical project and his argument about television and irony
  • The Illinois State Fair essay demonstrates that Wallace's method works on the most ordinary possible American occasion
  • The range — from film criticism to television theory to gonzo travel writing — shows the breadth of the methods

Minor Drawbacks

  • The David Lynch essay is the weakest major piece — substantial but less distinctive than the others
  • The tennis essays, while excellent, are minor compared to the major critical pieces
  • Readers unfamiliar with 1990s television culture may find 'E Unibus Pluram' more dated than the other essays

Key Takeaways

  • Television had taught a generation of Americans to be suspicious of sincerity, and that suspicion was a trap
  • Postmodern irony is not a position outside ideology but a form of complicity with the status quo
  • The cruise industry's systematic management of pleasure is a literal version of what entertainment culture does to consciousness
  • Fiction that wants to say something true must find a way to mean what it says
Book details for A Supposedly Fun Thing I'll Never Do Again
Author David Foster Wallace
Publisher Back Bay Books
Pages 368
Published February 1, 1997
Language English
Genre Essays, Literary Criticism, American Literature
Difficulty Intermediate
Best For Readers encountering Wallace's nonfiction for the first time, and those who want to understand the critical framework behind Infinite Jest; anyone interested in serious cultural criticism delivered with the energy of immersive journalism.

The Essay That Made the Argument

‘E Unibus Pluram: Television and U.S. Fiction,’ the collection’s centerpiece critical essay, was first published in the Review of Contemporary Fiction in 1993. It is the document in which Wallace made the argument that would shape everything he wrote afterward. American fiction, he argued, had spent the postwar decades learning from television — absorbing its self-referential irony, its awareness of being watched, its systematic undermining of sincerity. Writers like Barth and Pynchon and early DeLillo had used this strategy effectively, deploying television’s own techniques against it. But by the early 1990s, the strategy had been absorbed by the culture it was critiquing: television had learned to be ironic about itself, to acknowledge its own manipulativeness and laugh about it, and in doing so had defused the critique. Irony was no longer a weapon against the commercial culture of unreality. It was the commercial culture of unreality’s primary mode.

The argument had consequences for fiction that Wallace took seriously. A fiction that deployed irony as its critical tool was now doing the culture’s work for it. The writers who would actually advance fiction beyond its current impasse would be those willing to risk sincerity — to mean what they said, to acknowledge the vulnerability of caring about things, to be uncool in the service of being honest. Wallace knew how much he was asking. The essay is fully aware that the anti-ironic position it is advocating is itself available to be ironized, that the call for sincerity is the easiest thing in the world to dismiss. It is a document of a writer trying to think his way out of a trap that his intelligence made for him.

The Cruise Ship and the Management of Pleasure

The title essay — originally published in Harper’s in 1996 as ‘Shipping Out’ — is the piece for which this collection is remembered. Wallace takes a week-long Caribbean cruise on the MV Zenith and tries to be honest about what the experience is actually like when you pay full attention to it. The essay proceeds in Wallace’s characteristic mode: self-undermining footnotes, tangents that become the main argument, moments of genuine comic brilliance alternating with moments of genuine discomfort.

What Wallace finds on the cruise is a system designed to prevent the experience of being present to anything: an architecture of managed pleasure so comprehensive that it eliminates the possibility of genuine encounter, genuine boredom, genuine discomfort, or genuine reflection. Everything is provided, everything is smooth, everything is calibrated to produce a specific and guaranteed form of satisfaction that turns out, when you look at it directly, to be a sophisticated form of isolation. The essay’s comedy is inseparable from its analysis: the humor comes from Wallace’s hyper-consciousness colliding with an environment specifically designed to prevent hyper-consciousness from having anything to work on. He is, as he acknowledges, exactly the wrong person for a cruise, and the essay is the most honest possible account of why.

State Fairs, Lynch, and the Minor Essays

‘Getting Away from Already Being Pretty Much Away from It All’ — the Illinois State Fair essay — demonstrates that Wallace’s method works on the least glamorous possible occasion. He attends the 1993 fair as a journalist and tries to see it clearly, with neither the ironic distance of the sophisticated observer nor the nostalgic warmth of the booster. What he produces is a portrait of a specifically American form of community — temporary, commercial, structured around spectacle, genuinely enjoyed by its participants — that is neither condescending nor sentimental. It is harder than it looks, and its difficulty is the point.

The two essays on tennis — on the junior circuit and on Michael Joyce, the touring professional — anticipate the Federer essay that would appear in Consider the Lobster a decade later. They are the pieces in which Wallace first develops the argument that athletic excellence at the highest level is a philosophical subject, not just a sports subject, and that the specific demands of professional tennis — the required suppression of interiority that the pro game demands — illuminate questions about consciousness and performance that go well beyond sport. The Lynch essay, despite its length, is the weakest piece in the collection — astute in its observations but less formally daring than the journalism, less argumentatively coherent than the critical essays. The collection is uneven, which is the honest thing to say, and the unevenness does not diminish what the best pieces achieve.

Our rating: 4.3/5 — The collection that established Wallace’s voice and staked his critical position: that irony was a trap and that the escape from it required the kind of courage that only looks like naivety until you understand what it costs.

Frequently Asked Questions

What is "A Supposedly Fun Thing I'll Never Do Again" about?

Wallace's first essay collection includes his piece on the Illinois State Fair, an extended essay on David Lynch, 'E Unibus Pluram' on television and American fiction, and the title essay on a Caribbean cruise — the funniest and most formally inventive piece of literary journalism of the 1990s.

Who should read "A Supposedly Fun Thing I'll Never Do Again"?

Readers encountering Wallace's nonfiction for the first time, and those who want to understand the critical framework behind Infinite Jest; anyone interested in serious cultural criticism delivered with the energy of immersive journalism.

What are the key takeaways from "A Supposedly Fun Thing I'll Never Do Again"?

Television had taught a generation of Americans to be suspicious of sincerity, and that suspicion was a trap Postmodern irony is not a position outside ideology but a form of complicity with the status quo The cruise industry's systematic management of pleasure is a literal version of what entertainment culture does to consciousness Fiction that wants to say something true must find a way to mean what it says

Is "A Supposedly Fun Thing I'll Never Do Again" worth reading?

The collection that established Wallace as the most technically inventive journalist of his generation, and the one in which his central argument — that irony had become the default American mode and that fiction needed to find a way past it — received its fullest early expression.

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