The Castaway ⏤ On the Uses of Despair in ‘A Supposedly Fun Thing’

By Madeleine Adams

I

Right now it’s Friday 18 September, and I’m sitting on the corrugated iron patio of a chic, soulless café in the Clinton Hill neighborhood of Brooklyn, New York, listening to a woman on a Zoom call talk in a French accent about how their line of oils is underperforming and their new lotion has to be a success, and how “it’s going to be a journey to get there,” trying to summon up the hypnotic sensuous collage of all the stuff David Foster Wallace has seen and heard and done and written up as the result of his Harper’s assignment in 1995 on the 7-Night Caribbean Cruise on board the m.v. Zenith, which he curmudgeonishly refers to as Nadir, “a 47,255-ton ship owned by Celebrity Cruises Inc., one of the over twenty cruise lines that currently operate out of south Florida,” fifteen of which he goes on to list in the associated footnote. 

After this typically Wallacian catalogue of ships, whose encyclopedic elaboration of specs always humorously hints at the futility of capturing it all, getting everything down, he straightforwardly addresses the despair inspired by this cruise ship: “the word’s overused and banalified now, despair, but it’s a serious word, and I’m using it seriously.” 

Not quite dread or angst, this despair in “A Supposedly Fun Thing I’ll Never Do Again,” lurks beneath the surface of all social exchange, a shark circling its prey. It’s “more like wanting to die in order to escape the unbearable feeling of becoming aware that I’m small and weak and selfish and going without any doubt at all to die. It’s wanting to jump overboard.” In retrospect Wallace’s bald admission of suicidal ideation is what pop psychology might call a “cry for help.” But the question endures: How does one deal with such despair? Thirty years on, nobody seems to have a good answer to this question⏤most writers are unable to pose it with the same mix of zeal, good humor, and encyclopedic knowledge with which Wallace did⏤and in the meantime, Wallace’s oeuvre has received all kinds of backlash and praise. There’s the usual he’s-mean-and-a-misogynist-so-I’ll-never-read-him thing that women like the comedian Jamie Loftus (who put Infinite Jest in a blender and butt-chugged it) might say. “Too sweaty,” says Lauren Oyler in her piece for Harper’s in 2023 about the Goop cruise. Patricia Lockwood, in half-exasperation: “If his non-fiction is almost amniotically soothing, it is because we consent for the duration to let him do the thinking for us. He is the cruise ship, deciding where to dock, when we should retire to our quarters, whether to offer us an afternoon of skeet-shooting or ping-pong or chess with a nine-year-old prodigy.” 

Then there’s the re-evaluations: Gideon Lewis-Kraus (“the great writer-worrier of his time”); Zadie Smith (“he gave everything he had to his readers, including the kitchen sink”). Hermione Hoby, writing about reading Infinite Jest (“ a supposedly unfun thing I would do again and did”). 

Wallace’s despair in “A Supposedly Fun Thing” is broadly about the mismatch between the tiny scraps of experience that he’s able to articulate, and the infinite out-there-ness of a world whose signs, in their totality, drown the would-be interpreter in meaning. We are all humans with imperfect knowledge, suffering from moral weakness and the brute fact of our mortality. And if writing’s task is to represent the world with a sensitivity to all its subtle shades of meaning⏤which, in Wallace’s essays, involves confronting the fact that you are indeed “small and weak and selfish and going without any doubt at all to die” then that task will always inevitably fail. Setting yourself this impossible task moreover exiles you from the Eden that you, the tortured writer, imagine all the unbothered “normal” people (some of whom are your readers) live in. These others do not hold up essay collections to cover their shameful, bare ignorance. These others are probably not ashamed at all, but since you can’t know what’s in anyone else’s head, it’s impossible to really know, so you might as well add that to the list of things you, the tortured writer, don’t know and are tortured about. It’s enough to give you the howling fantods! 

One can only speculate on the three school papers Wallace tells us he wrote about “The Castaway” chapter in Moby-Dick where the poor cabin boy Pip, thrown overboard, beholds the terrifying immensities of the ocean and then, once hauled back onto the ship, tells the crew he saw “God’s foot upon the treadle of the loom.” The crew then judge him insane. “So man’s insanity is heaven’s sense,” concludes Melville. Wallace would certainly, pridefully agree. 

A philosopher’s alienation is also what Wittgenstein and Heidegger both expressed in their personal letters, a despair whose articulation they both inherited from Kierkegaard. Wittgenstein’s life felt like it was lived through a “closed window”; for Heidegger, other people “walk past outside as if on the other side of the window.” And it feels in many of Wallace’s “experience the Volk” essays like he stands outside the world, a stranger staring through his experiential window at a party; he’s a “giant floating eyeball” that’s all observer, and almost zero participant, even as he aw-shuckses his way out of just the invitation to the party he secretly maybe yearns for, using his disarming Midwestern affability.

But this alienation⏤this despair⏤ is Wallace’s strength. It’s generative⏤at its best, a Being-Towards-Death, which distances him enough from all the signs and symbols on board the Nadir to place them within an overall structure of feeling: “pampering.” We might call it in 2026 the “treat yourself you deserve it” ideology. To put it too neatly, the Nadir’s White Whale is satisfaction. And it’s as mythic and threatening to bodily sovereignty as a huge, supernaturally pale, leg-chomping leviathan. 

Everywhere, Wallace sees the promise of satisfaction spreading its hypnotic tendrils. The cruise’s advertisements and promises of pampering are “mesmerizing.” The essaymercial by IWW Chairperson Frank Conroy is “mesmeric.” Professional hypnotist Nigel Ellery, who mocks the passengers, making one shout “Weee Mommy I want a wee-wee!” and making another dance flamenco, and so forth, is a real exclamation point here w/r/t the whole hypnosis thing–even coming at the end of the essay. Celebrity Cruises offers you the chance to become entranced, to self-annihilate, to relinquish your freedom and return to a zombie-ish babyhood, or back even further, to the womb: “the windows’ spume a gentle shushing,” writes Wallace, “the engines’ throb a mother’s pulse.” 

Unkeepable promises sustain the capitalist industrial system, which, in the words of Lewis Mumford “thrives by stimulating wants rather than limiting them and satisfying them.” The cruise ship’s pampering imperative inflames the cruiser’s desire, rather than sating it: “A mental list of dissatisfactions and grievances that started picayune quickly become nearly despair-grade…” Wallace writes, listing the smallness of room service sandwich trays, the dill pickle soaking into his sandwich crust, the Port hallway being too narrow to leave the tray in the hall. But, he says, “the source of all the dissatisfaction isn’t the Nadir at all… [It’s the] ur-American part of me that craves and responds to pampering and passive pleasure: the Dissatisfied Infant part of me, the part that always and indiscriminately WANTS.” The cruise is a fantasy of relinquishing control, but any dominatrix or Existentialist will tell you that this is also itself an exercise of just that freedom that you wish to jettison. And if you can’t stifle that meta-awareness by maintaining the trancelike fantasy, then you’re going to have a bad time.

II.

Let me illustrate all I’ve said so far with an example. Two days ago, I went to a really nice hair salon, similar in sleek soullessness to the café where I am still sitting (I’ve moved tables, by the way, and have taken the seat of the luxury lotion Frenchwoman, who left twenty minutes ago. This new seat is undeniably better. Mine was missing a wooden back slat, so that I assumed a bit of a hunch while typing, but this one has all the slats intact plus a handy ledge to the right of the table for resting the remains of my matcha latté [NO SYRUP I commanded the barista. NO SWEETENER] and my notebook on. I’ve also switched to a pinot noir, chilled). I knew at this hair salon that I was going to spend way too much money on a cut and dye, just like last time. But, I reasoned with myself, I deserved it. After a summer filled with bee stings and allergic reactions to them, visits to urgent care and appointments with specialists, not to mention the other reminders of bodily breakdown I encountered this summer after our usual family trip to Maine was complicated by my 79-year-old father’s bout of fecal incontinence that required him to wear a diaper (Huggies not Pampers), my confrontation with death and its cousins (decay, breakdown, failure) entitled me to a treat. In fact, it entitled me to an Agent-Scully-Season 3-But-Blond treat. I was going to transform into the photo of Gillian Anderson I showed to the hairdresser (“but blond,” I told him.) The hairdresser concurred that I “deserve it.” In fact, over the course of three hours, when I told him about the bee stings, the vacations, (I didn’t go fully into the incontinence) he asserted that I “deserve” nice things. 

Now what did the hairdresser mean when he said that I deserve nice things? This bothered me for the rest of the appointment. Did the playlist cater precisely to my millennial taste in order to pamper, or was it because the hairdressers like Counting Crows? Did my hairdresser really want to offer me a cup of tea, or is it just written in the salon’s instruction manual? Did he sincerely believe that I “deserve nice things,” or is it simply something that he’s expected to say because he works at a luxury salon in Brooklyn, whose whole telos is to provide nice things to its clients under the premise that they somehow “deserve” them? Did he in reality think I was just some spoiled bitch, but couldn’t say it? Wallace encounters a similar conundrum with the chambermaid Petra, who cleans Wallace’s cabin thoroughly and frequently. It’s “like having a mom without the guilt” (every man’s dream!) But… it’s not quite that. Petra doesn’t clean his room because she likes him and thinks he’s, as she says “No Problem” or “A Funny Thing.” No, she’s under orders to do so. “She’d clean my cabin just as phenomenally well even if I were a dork,” says Wallace.

The unctuousness required by the pampering imperative also compels my hairdresser to tell me, “You deserve nice things” and to also scritch my head in a nice massage during the shampoo. Though no one ordered him explicitly to use exactly this language or this scritching pattern, nor did anyone tell Petra to call Wallace “No Problem,” they present the same issue of authenticity. Is everyone in the world just pretending they like each other in order to maintain a nice illusion so that they can swipe a profit off each other, in some cynical perversion of the social contract? Are we all just French luxury lotion salespeople on Zoom calls with each other trying to sell our brands? 

I began to wonder this quite anxiously, especially when I looked in the mirror and realized my haircut made me look like a scolding librarian. How can we know anyone’s intentions towards us when they promise us anything?  I went to the Belgian restaurant down the street from me yesterday to get a phenomenally decadent lunch to make myself feel better about my bad haircut and growing sense of alienation and to continue writing this essay. Here, I hoped, was a real thing that I deserved and that I would finally get, in its fully satisfying form. But it was difficult not to feel suspicious of the host’s smile and assurance that coming in and working on a laptop wouldn’t be a vibe-killer for the other patrons, that he was pleased to offer me the nice table in the corner by the door, which he would happily prop open with a brick to let in the fresh autumnal air, just for me, since I asked to be near a window. Yes, there is a charging bank, Hugo said without a hint of annoyance at my questions and finicky needs. Did Hugo smile so charmingly at me as he set the menu down only because his job required it of him? And the smoked trout, the gruyere and potato croquettes, the green beans… Did the chef make them that way because he sincerely believed I deserved them? I don’t know! Did I need to feel a sense that Hugo and the chef believed I deserved it in order for the food to taste good? I don’t know!  But if everywhere insincere “pampering” can pass itself off as kindness, then must we always be on the lookout for false promises designed to inflame our desires, for White Whales that we spend our meagre earnings chasing while we turn into despots of pleasure?  What does it even feel like to be given a real, tangible, good-for-you good? 

This question becomes more pressing as our media landscapes cocoon us in more and more layers of pampering and ataraxia, while the world “out there” seems less stable and more hostile. Like a cruise ship, like a luxury lotion, we can cover ourselves in sensory blankets of music and memes, what Marshall McLuhan describes as a numbness akin to the effects of an audiac, a post-World War II device that played very loud sounds through headphones so that dental patients didn’t feel any pain from the drill without anaesthetic. A more sophisticated version of the “therapeutic” numbing of media stimulation is starkly illustrated in Ben Lerner’s Transcription when a character recounts a story about his pre-teen daughter, who has been unable to eat normally since the age of eight, not from anorexia but from avoidant/restrictive food intake disorder whose origin is a mystery. Finally, after years of extreme measures that all fail, she watches ASMR and YouTube videos of people unpacking boxes, and is miraculously able to eat while she watches. “The clips are full of the sounds of plastic wrap crinkling, paper rustling, and the gasps and infantile gurgles of excitement from the unboxer, who taps on everything with her long pink nails.” Why, her father wonders, do these semi-pornographic videos help?  “It’s satisfying,” the girl explains. 

“And she seemed to mean the satisfaction of a kind of physical need: while she was watching a flattened image on a screen, all those mouth sounds and little taps and crinkles provoked a low-level somatic response, scratched a kind of itch. It’s like the device takes you out of the real world, shields you from all the pressures and information, but then it administers this series of subtle sensory inputs and muffled shocks, these mild effects, as compensation for the unmanageable reality it’s made disappear.”

It feels like reality, with its high expectations, its unlivable wages, its floods and forest fires, its totalitarian takeovers, and its school shootings, punctures our psyches. Taking refuge in the numbing cocoon of simulacral media isn’t simply a “treat yourself you deserve it” luxury⏤”satisfaction” of this sort is a matter of survival. Despair can kill you, as Wallace’s early death so gruesomely illustrates.

III. 

Anxiety, angst, sorrow, fear and trembling, nausea… Wallace came by it honestly. A very clear lineage links him to the ancient tragedians: from Aristotle and Augustine to Kierkegaard, and continuing through Heidegger, Wittgenstein, and the existentialists. I can’t go through all these thinkers’ iterations of The Bad Thing, but I found Kierkegaard, whom Wallace doesn’t really engage overtly with, to resonate quite a bit with “A Supposedly Fun Thing” and its conception of despair⏤perhaps because Heidegger and Wittgenstein, Wallace’s touchstones, cribbed so heavily from him.

In Kierkegaard’s Either/Or there is a dichotomy between the esthete and the mystic. Either you are the seducer, the cad, the effusive lover of Mozart, with whom the world laughs⏤or else you are the sad and miserable poet, the unloved mystic, martyr, or philosopher, wallowing in sorrow. Thus the title of the book Either/Or which poses this choice (a totally arbitrary one by the way– good luck pal) as the primary exercise of one’s freedom. It’s just this dichotomy that Wallace also constantly chose between, e.g., the Charlie Rose interview six weeks after the publication of A Supposedly Fun Thing especially. In that interview, Wallace sweats and grimaces his way through the phatic gum-flapping of his erudite host, who pokes fun at him for worrying about how he might come off. Wallace snaps, “You confront your own vanity” when you’re on TV.  “Writing for magazines is a weird thing,” he adds. “Part of you is a nerd, you just want to sit in libraries and not talk to anyone and be very shy, and the other part of you is the worst ham of all time⏤ ‘Look at me, look at me!’”

Heidegger, too, writes about “thrownness” or “falling into” the world⏤we are so tranquilized by the everyday world’s temptations, so beguiled by its “idle talk,” its petty intrigues and curiosities, that we become delightfully lost in and entranced by our own and others’ inauthenticity, as though we wandered through the loveliest maze imaginable, with a party going on in it. Sometimes we even get entangled in our own internal mazes, (What should I wear? Who should I flirt with?) but then even that anguish is enjoyable. It is simple anguish over which turn to take in the maze. “Distracted by distraction from distraction” in T. S. Eliot’s words. 

We are absorbed in the world. “Look at me! Look at me!” Only when we think about what might be outside the maze⏤only when the world (when we realize its contingency and insignificance) falls away from us—do we confront real anxiety. We are no longer able to fall into the world, but rather we flee from it and from ourselves. “Anxiety,” Heidegger writes, “reveals the nothing.” 

A real, tangible, good-for-you good, then, would not be something that assuages or brushes aside this anxiety; it wouldn’t be entertainment. It wouldn’t be a cruise ship hypnosis session. It wouldn’t be watching someone ham it up for a TV audience going “Look at me! Look at me!” “Entertainers can divert and engage and maybe even console; only artists can transfigure,” Wallace writes in the posthumous essay “Fictional Futures and the Conspicuously Young.” Television and the sort of pleasure it produces, Wallace suggested, is a denial of the truth, and is therefore not transfiguration. The same could be said of the entrancing delights of the 7-Night Caribbean Cruise, whose promises of total satisfaction have a hollow, sinister, yet seductive ring. Viewers don’t like it when the hero dies, because it makes the distraction unsexy. They don’t like being small and weak and selfish and mortal. It’s not hot. But these reminders of our terrible freedom and the burden of choice such freedom entails are what tragedy teaches us. Borrowing from Aristotle, Kierkegaard warns: “In losing the tragic the age gains despair.” If we forget how to die, we forget how to live. If love is an invention, and the poets its inventors, as Leslie Fiedler writes, then despair, too, is an invention that the tragedians invented⏤to teach us how to confront it. 

So what do we do with all the shitty soap opera writers? What about the Petras and Frank Conroys and French luxury lotion salespeople and hairdressers and hypnotists and Hugos? What about the ASMR video influencers? Well, being reminded of this “small and weak and selfish” etc constantly would produce a nervous wreck. Imagine a society constantly in a state of anxiety or despair, or sorrow⏤a society of pure melancholics. Grocery store clerks would weep instead of ringing up your bananas. Garbagemen would lie cataconically in the street. Luxury lotion would remain in warehouses, perhaps even exploding in thick goopy spurts. And so this despair can only be administered occasionally, through tragic (or at least tragicomic) art, with authenticity at its center.

For Heidegger, it’s practicing care born of just the anxiety we wish to not confront but that, if we’re lucky enough, we do confront. So for the artist, as for anyone practicing philosophy, the task is, in Wittgenstein’s words, “to show the fly out of the fly bottle.” Ew! It’s not always a fun task. But in that same Charlie Rose interview, Wallace says of David Lynch “the really great artists are entirely themselves. They’ve got their own vision, their own way of fracturing reality, and if it’s authentic and true you will feel it in your nerve endings.” It is a gift bestowed on you⏤the ability to create. You pass that creation along to others, in a Trobriand Islander kula ring, not as a commodity. The process of authenticity is, like Wallace’s attempt to gain his footing on the hypnotically swaying boat, “a meditative exercise to stay conscious of what’s going on.”