Throughout the 1990s, few authors sought to redesign the literary language quite like David Foster Wallace. Along with his maximalist magnum opus, he was a regular culture critic known for his detailed essays that pushed far beyond the page and into the footnotes. Nowhere is this clearer than in his essay collection "A Supposedly Fun Thing I'll Never Do Again," which finds him interweaving the hot topics of the day along with personal perspectives that turn academia into an accessible and sometimes emotion-driven art form. One doesn't need to be a fan of tennis, state fairs, or David Lynch to appreciate what Wallace has created. It's such a succinct look at what drove the writer that it becomes one of the essential portraits of a period in American history that was both full of ambition and farce. In some ways, these essays surpass his fiction, introducing a new way to think of the world, even if there's things about it that he doesn't care for.
Unlike most anthologies, the title is a thematic connection between each of the essays here. Despite being the name of the closing piece where he goes on a confounding boat cruise, it can be applied as a tragic study of the world he observes elsewhere. For example, the opening essay is more autobiographical, serving as a love letter to his Illinois hometown that was so flat that it inspired his love of math. It's where he would learn to play tennis before finding numerous setbacks which, in itself, became tragic once he attempted to branch out to other courts. His expertise shines through as he belabors minor details about math and sport, eventually tying it into his weekly trips to tournaments that grow increasingly hopeless. Everything ends with the central "supposedly fun thing," of which ends his career and puts a bittersweet button on the experience.
Not every story is about Wallace, but he's at times the most ominpresent essayist since Joan Didion. It's there in his view of the Illinois state fair, or a trip to the movie set of Lost Highway, where he attempts to understand what David Lynch's deal is. It's in moments like this where the passion shines through, especially as Wallace preludes his trip with lengthy film theory on Blue Velvet: a film that reshaped how he saw media as a greater concept. He ultimately doesn't have a concrete answer, but his effort to look for answers between intellect and the visceral drives a compelling argument for why people consume art in the first place.
Then there are the essays where he's less involved, including a groundbreaking, career-defining essay where he destroys the concept of irony. Like most entries, it's a bit daunting in length and requires patience to fully get the point across. However, those willing to hear his studies of media and marketing will find a greater point emerging about irony's lack of edge. By tying it into decades of TV and literary culture, including a lengthy study of post-modernism like Don Delillo, he finds that sarcasm is often used less to provoke and more to evoke humor and nonsense. The only way to fully appreciate his wisdom is to read the piece and determine whether his plea for sincerity is ultimately the right one. Still, it explains why he often felt at odds with the world, wishing to see past crass consumerism and shallow marketing. In some ways, he was making himself intentionally miserable even as he presented some profound talking points.
Beyond the talking points, "A Supposedly Fun Thing I'll Never Do Again" is an excellent mix of humor and creative thinking. It's a chance to dig into where the culture was at the time while exploring the small moments that seem insignificant, but hold the greater clues for what drives our behaviors. What puts it over the edge of mere finger wagging is the sense that Wallace wants to start a conversation and make the world a better place. In theory, all he could do was inspire conversation. In that regards, there's a lot of persuasive arguments within these pages. Not all of them will change how you see the world, but the sincerity keeps everything from being smug or dubious. It's genuine expression at its finest.
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