Short Stop: #10. David Foster Wallace – “A Supposedly Fun Thing I’ll Never Do Again”

Over the past few series, Short Stop has focused on stories that fall under the fiction umbrella. While some have been autobiographical, they present something more creative within the framework that is deserving of exploration. The chance to dive into what interests an author becomes a rewarding experience as I broke down themes and found interesting tidbits. While this will be the same for the upcoming series, the approach will be a little different. I’ve been a fan of David Foster Wallace ever since reading “Infinite Jest” years ago and have been curious to delve into his essays. In an effort to better understand his potential as a writer, I am going to be spending this column exploring the seven entries for “A Supposedly Fun Thing I’ll Never Do Again.” Will the mix of analysis and autobiography provide something rewarding, or will I never do a nonfiction column again? Join me and find out. The only caveat is that due to some of these being lengthier, there’s an off chance the entries will take longer to release. Keep that in mind and let’s delve into one of the most unique voices of the late 20th century.

Prior to this column, my awareness of Wallace was his fiction. While I found it innovative, it’s hard to say that I was appreciative of his greater gifts. The value of the form is that there’s enough distance and the reader is left assuming things about the author. One could read autobiographies and interviews to fill in the gaps, but it’ll never be the same as hearing what they had to say. The value of Wallace was his candidness within the larger text, where you understood where he stood on his subjects. In some ways, he borrowed the first person perspective of writers like Roger Ebert or Joan Didion who made you feel more involved with the culture. It’s there in how he talks about playing tennis or watching television. Everything feels grounded in a moment to the point that picking up his personal tics creates a parasocial relationship. I have never been to the Illinois State Fair, and yet because of him I feel like he’s telling me stories while overlooking the carnival rides. Love or hate him, but he is one of the most transparent critics of the 90s. Where most would put information before self, his ability to meld is a testament to his craft.

The essay “A Supposedly Fun Thing I’ll Never Do Again” resonates with me. While I have found comfort in watching reruns of The Love Boat, the fantasy of taking a cruise disinterests me. Unlike Wallace, I am not opposed to riding a boat on the ocean. I’ve been on my dad’s smaller ship for hours in the early 2000s trying to not get caught up in the choppy waves. I don’t even know that it’s the idea of a floating hotel – which I don’t even visit on land regularly. Whatever skepticism I had escalated around 2020 when it was reported that a cruise was full of quickly spreading Covid-19 patients. Even those isolated contracted it through the air vents. This sounds like a nightmare and no matter how much I want to travel, I don’t know that my mentality is built for the manufactured joy of its week-long promises.

More than anything, Wallace’s issue with the cruise is its larger inauthenticity. The autobiographical nature of this collection has already made me assume the nature to which he’d take to being pampered, but even then it’s no match for the 24/7 nature of his surveillance here. He’s socially awkward and suffers from agoraphobia, meaning that small changes fill him with dread. In one of the finest footnotes I’ve ever seen him write, he talks about Professional Smiling as a concept and how it upsets him because it’s dishonest. It’s to please the customer while missing the larger point. As someone from a no-name Illinois town just outside Chicago, it makes sense that Wallace wouldn’t be keen to special treatment. Frankly, the nature with which his hotel is constantly “reset” to its cleanliness reads like a fantasy story. Where does the maid come from? How does she work so fast? She’s not the only one who seems overeager to please, but given that it’s Wallace’s source of privacy, it’s bothersome to know he has to confront his existentialist fears because he doesn’t feel deserving of a spotless room.

It's a notion that I agree with. Maybe our levels of expectations differ, but I am uncomfortable at the thought of “being watched” in moments of leisure. I get that they’re employees doing what they can to satisfy a quota, but when you’re mostly used to the Denny’s treatment, you find the gradual service better. I want flaws. I don’t want the infantile feeling of needing everything done for me. It becomes helpless and I think makes the service workers also seem all that more distant. Having worked at a grocery store, I sympathize with employees who are just that bit slower. If anything, it sets unfair expectations for everyone and leads to spoiled customers complaining that anything short of perfection is bad.

Much like his visit to the State Fair, there is standing around and observing the communities around him. There are those who attend ritualistically and have fond memories. Others are so blasé that they become unofficial villains in Wallace’s life. At one point he talks to a teenager who is the embodiment of 90s white suburban kid who is into hip-hop. The goofiness has only sweetened thanks to how dated that concept has become over time. Elsewhere he recalls how a dining mate is a young girl who is spoiled by a kind grandmother that mostly pleases her to keep from any upsets. At this point he even sympathizes with the waiter who is eager to have truthful reviews. If Wallace likes the food, he mustn’t just say “fine.” He needs to use more sensational words. Everything reads like a survey on how to improve service. They’ll be seeing each other for seven days and need to not be reduced to awkward glances.

Something that’s endearing about Wallace is that he’s so much of an introvert that you can feel his discomfort on each of the 100 pages. Even as he talks to others, there is disconnection from the party atmosphere. He is not built to give into these whims and instead is desperate for something authentic. This isn’t too dissimilar from “E. Unibus Pluram” where he rails against writers participating in a dull tradition of irony. He is bothered by the willingly empty gestures of both, even if it produces a lot of comical set pieces. He recounts the journey of a man with a handheld camera who films everything. At one point he’s even seen recording people on shore who are recording him back, creating an infinite loop of meaningless documentation. 

I think what keeps this from being unbearable is that Wallace seems eager to understand his environment. He desperately wants to be one with the feeling that the hundreds around him regularly feel. The struggle turns the text into this contemplative study of isolation in a capitalist society, where excess is greater than any sense of fulfillment. There is a need to participate in the endless events in order to feel “involved.” It’s an exhausting line-up that requires almost zero sleep or actual sense of leisure. There’s so much to do that the “supposedly fun” part becomes a chore, and it makes one want to reject the whole notion. For as fascinating as it is to see Wallace sit in on church functions and magic shows, they ultimately feel like distractions until everything ends.

More than anything, this essay helped me appreciate the recent Jenny Nicholson essay on The Star Wars Hotel. Where I’ve found the four hour video essay format to be interminable and unfocused, I’m now seeing that it’s part of a larger tradition. I prefer Wallace’s approach because it feels autobiographical and personal. Maybe it’s because he built trust with me, but I was entertained even as he delved into the minutiae that is too tedious. All of the complaints he has of dealing with staff refusing him journalist access to events feels like a slight against our hero. I want to see Wallace win because this is as much a product review as it is a psychological study. While Reagan-Era culture would suggest a cruise is the height of luxury, having someone sincerely admit his disinterest feels revolutionary. He feels primed to be a 90s icon not because he’s rebelling in a flamboyant way but something more quiet and intellectual. He’s driven by a quest for authenticity, and anyone who’s watched The Love Boat could already tell you how hard that is to achieve in this vicinity

Is there any value in placing this last in the collection? I think it would’ve been too exhausting as an entry point. There is a need to build trust with the reader before really delving into some heady material. For as many entries that don’t feel like a congruent whole, this feels like a journey through 90s American idealism that is unlike any other perspective. I’m sure there would be those who were more sensationalistic, but Wallace was always obsessed with exploring life as an addiction. He’s curious to understand why he’s interested in any of this. While I think it doubles as this incredible study of mental illness through social disenfranchisement, there’s this questioning of what values America should be worried about. In spite of common tropes of an “MTV Generation” mentality that worships Beavis and Butthead, he’s trying to elevate Gen-X’s identity into something respectable. 

As a result, I am left with the conflicting opinion that even if these aren’t entirely my favorite essays I do find a deep kinship with Wallace on an intention level. I don’t believe I could ever write something this exhaustingly specific in my life. My type of trust is more designed with insinuation, where only the important details are on display. Maybe that’s why Wallace is so revered. His ability to go line by line through an idea is powerful stuff and he encourages rethinking about the world around you. The “E. Unibus Pluram” essay is one of the great media analyses I’ve read. There are points along the way where he gets me to sympathize through a mix of facts and pathos. He’s finding the humanity in his topics, and I love going along with him for the journey even if they’re way too committal for regular consumption.

Another thing that I love is that even as he writes about the meandering nature of a cruise, he decides not to end with the final docking. Among the fun stories of failing at chess and skeet shooting he finds himself just desperately trying to give into the façade and failing. That is why the final magic show is such a perfect button. It’s not the most important event of the trip, and yet it symbolizes the greater struggles. As people willingly are put under hypnosis, the audience laughs at the artifice. Predictably, Wallace doesn’t fall for it. Instead he leaves at the end, unsatisfied by what he’s just witnessed.

To return to a larger thesis for this column, I want to answer whether this “supposedly fun” journey of analyzing non-fiction is worth doing again. I still prefer fiction and think that there would come a point where I’m just writing personal essays instead of the author’s intent. While I would love to cover Wallace again, I feel like the more generalized forms of analysis will prove difficult to do with any level of insight of entertainment. I’m sure I’d get a lot out of them, but I’ve found authors like William Faulkner, Jhumpa Lahiri, or Alice Munro to be more interesting through their implications. For the time being, I will be looking for collections that emphasize something closer to my norm. I get the irony of covering Wallace, who is more than supposedly fun, only to never do non-fiction again. I promise that it’s not off the table, but whatever I cover in 2025 will be more in line with tradition. Thanks again for the prose, Wallace. I loved spending time with you. I hope to see you around more.

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