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A Supposedly Fun Thing I'll Never Do Again (essay)

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“A Supposedly Fun Thing I’ll Never Do Again” is the namesake essay from Wallace’s larger collection of non-fiction pieces. The essay was originally published as "Shipping Out" in Harper's in 1996. Sent by Harper's on a 7-Night Caribbean (7NC) Celebrity Cruise aboard the m.v. Zenith, which he rechristens the Nadir, Wallace describes what he sees as the middlebrow excesses exhibited during his trip. The essay is characterized by its truly Wallacian uproarious humor, and by its exploration of some of the most basic yet most unconsidered aspects of the human condition.



A common theme in both his fiction and non-fiction writing, in “A Supposedly Fun Thing” Wallace explores the specifically American activities of consumption and tourism. As Wallace stands on the deck of the Nadir and watches his fellow passengers move ashore in Cozumel, he writes that “looking down from a great height at your countrymen waddling in expensive sandals into poverty-stricken ports is not one of the funner moments of a 7NC Luxury Cruise” (310). To Wallace, there is something incredibly “bovine” (310) about American tourist groups, “a certain greedy placidity about them. Us, rather” (310). He is so disgusted with what he sees that Wallace is hesitant to name himself as a part of that group. The greed and thoughtless group-like mentality that Wallace witnesses lead him to decide that in port, we become “The Ugly Ones” (310). This sense of disgust at American tourism and consumerism makes him incredibly “newly and unpleasantly conscious of being an American” (310). “Part of the overall despair of this Luxury Cruise is that no matter what I do I cannot escape my own essential and newly unpleasant Americanness” (311). The despair Wallace associates with American consumptive tourism is something he explores in his essay “Consider the Lobster” as well. After a trip to the Maine Lobster Festival, Wallace expounds that “To be a mass tourist, for me, is to become a pure late-date American: alien, ignorant, greedy for something you cannot every have, disappointed in a way you can never admit” (CTL 240). And in just the same way, on the cruise, Wallace looks down onto the pier and knows that “whether up here or down there, I am an American tourist, and am thus ex officio large, fleshy, red, loud, coarse, condescending, self-absorbed, spoiled, appearance-conscious, ashamed, despairing, and greedy: the world’s only known species of bovine carnivore” (311). His disdain is tangible.

Selling the Fantasy

Related to his discussions of American consumerism, Wallace spends part of the essay describing the art of selling the cruise vacation fantasy. He describes how the Celebrity Cruise’s brochure uses the second-person pronoun throughout its pages. In this way, “in the brochure’s scenarios the 7NC experience is being not described but evoked. The brochure’s real seduction is not an invitation to fantasize but rather a construction of the fantasy itself” (266). Wallace explains that there is a certain “authoritarian twist” (266) to the Celebrity advertising. Whereas normal advertising shows you other people, on TV or in an ad, enjoying a certain experience, thereby allowing you to fantasize about yourself in such a scenario, “in the cruise brochure’s ads, you are excused form doing the work of constructing the fantasy. The ads do it for you. The ads, therefore, don’t flatter your adult agency, or even ignore it—they supplant it” (267). In this way, Wallace notes that the ads make a promise “not that you can experience great pleasure, but that you will” (267). Wallace expounds upon the consequences of such a promise: “Your troublesome capacities for choice, error, regret, dissatisfaction, and despair will be removed from the equation….because you will have no choice but to have a good time” (267). Wallace’s analysis contains somewhat foreboding undertones as he recognizes the absurdity of giving yourself over completely to a cruise ship for seven days. From the moment you read that first ad in the Celebrity brochure you have given up all control and have placed it into the hands of others.

In another section of the essay, Wallace discusses the fact that the Iowa Writers Workshop Chairperson, Frank Conroy, has written an essay for the Celebrity brochure. But, the catch is that Celebrity Cruises had paid Conroy to write it. Such a fact “reveals once again the Megaline’s sale-to-sail agenda of micromanaging not only one’s perceptions of a 7NC Luxury Cruise but even one’s own interpretation and articulation of those perceptions” (287). Again, all free choice is taken away the second you begin reading the brochure. But the even larger problem that Wallace sees in Conroy’s “prostitution” is that Celebrity Cruises presents Conroy’s writing as an essay instead of as an advertisement. For Wallace, “an essay’s fundamental obligations are supposed to be to the reader” and therefore the reader approaches an essay “with a relatively high level of openness and credulity” (288). But a commercial or advertisement is much different. The reader knows that “whatever attempts an advertisement makes to interest and appeal to its readers are not, finally for the reader’s benefit….and this is part of why our state of receptivity is different, more guarded, when we get ready to read an ad” (289). Therefore, touting Convoy’s ad as an essay “messes with our heads” (289). We begin to mistake art for advertisement and vice versa. Ultimately, Wallace decides that the Convoy “essaymercial” is the “perfect ironic reflection of the mass-market-Cruise experience itself….It seems to care about me. But it doesn’t, not really, because first and foremost it wants something from me” (290).


The Professional Smile

While on the Nadir Wallace concerns himself regularly with the notion of appearances, both with the appearances of those around him as well as his own appearance. He is especially interested in the notion of what he calls the “Professional Smile”: “a national pandemic in the service industry” (289 fn 40). He goes on to claim that he has encountered more Professional Smiles on the Nadir than he has anywhere else. He describes the special smile as “the smile that doesn’t quite reach the smiler’s eyes and that signifies nothing more than a calculated attempt to advance the smiler’s own interests by pretending to like the smilee” (289 fn 40). Wallace admits that “high doses of such a smile produce despair” in him (289 fn 40). Just as he feels manipulated by the Conroy’s “essaymercial,” Wallace doesn’t enjoy being fooled by the Professional Smile into thinking he’s liked or appreciated. Yet, Wallace concedes that “the Professional Smile’s absence now also causes despair. Anybody who’s ever bought a pack of gum in a Manhattan cigar store…knows well the soul crushing effect of a service worker’s scowl” (290 fn 40). Wallace notes that because he has gotten used to the Professional Smile, he now walks away “from the Manhattan tobacconist resenting not the counterman’s character or absence of goodwill but his lack of professionalism in denying [him] the Smile. What a fucking mess” (290 fn 40). The false Professional Smile both instills despair in Wallace, but also creates a standard of “professionalism” in his mind, with which he now judges all service-industry people by. Both false and true appearances now no longer have any meaning.


Besides paying attention to the appearance of others, Wallace also pays nearly neurotic attention to his own appearance as it is perceived by the crew and his fellow cruisers on the cruise ship. The most obvious example of Wallace’s concern over his own appearance is when he calls for room service in his cabin. He writes:

Usually what I do is spread out my notebooks and Fielding’s Guide to Worldwide Cruising 1995 and pens and various materials all over the bed, so when the Cabin Service guy appears at the door he’ll see all this belletristic material and figure I’m working really hard on something belletristic right here in the cabin and have doubtless been too busy to have hit all the public meals and am thus legitimately entitled to the indulgence of Cabin Service. (296)

Wallace essentially creates a false image of himself in order to justify, to whoever will bring him his food, his need to order Cabin Service when there are so many other eating options available on the ship. He seems to have a fear of being judged. In this particular case, his need to create an outward appearance also stems from the guilt that he feels from indulging in such extravagant pampering. But, he ultimately creates a façade for himself in order to escape judgment or criticism from whomever he comes across.

He also admits that in response to viewing his fellow Americans as a pack of bovines, he has tried to create an appearance of himself opposite to those around him: “All week I’ve found myself doing everything I can to distance myself in the crew’s eyes from the bovine herd I’m part of, to somehow unimplicate myself: I eschew cameras and sunglasses and pastel Caribbeanwear; I make a big deal of carrying my own cafeteria tray and am effusive in my thanks for the slightest service” (311). Such instances of Wallace’s self-consciousness stem from his own dissection of everything and everyone around him. Because Wallace notices and reports on all of the minute eccentricities and oddities of all the other people on the ship, his own self-consciousness belies the fact that he doesn’t want to fall victim to any criticism himself. He seems to have a slight fear of being that person that he makes fun of or judges. So when he can, he tries to make himself seem as he wants others to see him, in order to avoid putting himself in a position that might allow others to scrutinize him in the same way he analyzes others. Such concern might also point to a sense of guilt or self-reproach over his treatment of others’ appearance.


Wallace spends much of the essay discussing the excessive pampering of a 7NC cruise and the subsequent guilt he feels because of it. He mentions example after example of the ways in which the cruise attempts to exceed his expectations: “each upper deck’s carts are manned by a special squad of full-time Towel Guys, so…a Towel Guy materializes the minute your fanny leaves the chair and removes your towel for you and deposits it in the slot” (293). And, in the “Five-Star Caravelle Restaurant, the waiter will not only bring you, e.g. lobster…with methamphetaminic speed, but he’ll also incline over you with gleaming claw-cracker and surgical fork and dismantle the lobster for you, saving you the green goopy work that’s the only remotely rigorous thing about lobster” (294). There is no end to the pampering on board the Nadir as Wallace goes on to explain for several more pages the cleanliness of the ship, and the accessibility of room service, and especially the invisible yet constant cabin cleaning. Yet in facing excessive pampering Wallace beings to break down:

[I]t’s my experience with the cabin cleaning that’s maybe the ultimate example of stress from pampering so extravagant that is messes with your head….I fully grant that mysterious invisible room-cleaning is in a way great, every true slob’s fantasy, somebody materializing and deslobbing your room and then dematerializing—like having a mom without the guilt. But there is also, I think, a creeping guilt here, a deep accretive uneasiness, a discomfort that presents—at least in my own case—as a weird kind of pampering-paranoia. (297)

This pampering-paranoia comes from Wallace’s realization that his room is not being cleaned by Petra (his cabin steward) because Petra cares about him, but because it’s her job. This leads Wallace to ultimately ask: “if pampering and radical kindness don’t seem motivated by strong affection and thus don’t somehow affirm one or help assure one that one is not, finally, a dork, of what final significant value is all this indulgence and cleaning?” (299). This is the heart of the issue for Wallace. What do Americans gain by being pampered by people who they know don’t actually have a vested interest in their well-being? Does anyone even realize that they are being pampered by someone who most likely resents the fact that it is her or his job to pamper you in the first place?

Not only does the pampering induce guilt, but it also creates an unfulfillable void. The Celebrity brochures want to make you believe that “this Ultimate Fantasy Vacation will be enough pampering, that this time the luxury and pleasure will be so completely and faultlessly administered that my Infantile part will be sated” (316). But, Wallace notes, the Infantile part of anyone is insatiable, for the entire “essence” of the Infant is it’s “a priori insatiability” (317). This leads Wallace to conclude that “in response to any environment of extraordinary gratification and pampering, the Insatiable Infant part of me will simply adjust its desires upward until it once again levels out at its homeostasis of terrible dissatisfaction” (317). For after a few days on the Nadir, Wallace beings to notice everything that is wrong with it: “when Petra makes my bed not all the hospital corners are at exactly the same angle…[and] the ice sculptures at the Midnight Buffet sometimes look hurriedly carved” (317). The pampering induces the need for more. So, in the end, all of the pampering not only induces guilt, but also makes for even more dissatisfaction once one's inner Infant starts crying again.


While one normally goes on a cruise to find relaxation and a sense of happiness, Wallace finds that “there is something about a mass-market Luxury Cruise that’s unbearably sad” (261). This sadness remains as an undertone to the entire piece—a reminder of Wallace’s finely attuned consciousness of the true sadness that is our culture. Wallace continues on to explain that “especially at night, when all the ship’s structured fun and reassurances and gaiety-noise ceased—I felt despair” (261). Wallace notes that the word despair has become a banality, but insists that he uses it in all seriousness. For Wallace, the word despair “denotes a simple admixture—a weird yearning for death combined with a crushing sense of my own smallness and futility that present as a fear of death….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” (261). The notion of awareness or consciousness creating suffering or despair is a common theme running throughout Wallace’s work. Here, on the ship, Wallace is faced with a slice of American culture, a slice filled with extreme consumption, greed, falseness, laziness, irony, and pampering. After examining the manipulative and authoritarian advertising of the Celebrity Cruises, Wallace writes that the spuriousness of the ad “causes despair” (289). And as he watches his fellow cruisers scuttling about like ants onto shore and into their role as tourists, Wallace confesses that “part of the overall despair of this Luxury Cruise is that no matter what I do I cannot escape my own essentially and newly unpleasant Americannes” (311). As Wallace is forced to examine all of these horrible traits of American culture, he is also led to examine his own place among them—thus leading him into a pit of despair.

Death and Transcendence

The tangible despair Wallace endures while on the cruise ship also leads him to thoughts about death and the ways in which we attempt to transcend it. Wallace notes that the Luxury Cruise appeals most to older people (50+), people “for whom their own mortality is something more than an abstraction. Most of the exposed bodies to be seen all over the daytime Nadir were in various stages of disintegration” (263). He also sees that “the ocean itself…turns out to be basically one enormous engine of decay” as the salt corrodes almost everything (263). These observations lead Wallace to pointedly state: “A vacation is a respite from unpleasantness, and since consciousness of death and decay are unpleasant, it may seem weird that Americans’ ultimate fantasy vacation involves being plunked down in an enormous primordial engine of death and decay” (263). Wallace questions Americans’ desire to escape to a place where older decaying bodies and corroding objects are plentiful.

But, the reason we are able to put ourselves in such a position, Wallace says, is because “on a 7NC Luxury Cruise, we are skillfully enabled in the construction of various fantasies of triumph over just this death and decay” (264). Wallace expounds upon three ways that we attempt transcendence of death:

1. “[V]ia the rigors of self-improvement” or “titivation” (264). Wallace notes how the crewmembers on the Nadir are constantly scanning the ship for any signs of decay, for as soon as they spot something they immediately take measures to fix it. In the same way, many of us are constantly trying to hide and cover any signs of our own mortality through methods such as “diet, exercise, megavitamin supplements, cosmetic surgery, Franklin Quest time-management seminars, etc” (264).

2. “Not hard work but hard play” or “titillation” (264). The cruise’s “constant activities, parties, festivities, gaiety and song; the adrenaline, the excitement, the stimulation” (264) allow us to feel alive. But, Wallace notes that the constant parties and activities “promise…not a transcendence of death-dread so much as just drowning it out” (264).

3. And finally Wallace explains that the Celebrity brochure contains phrases such as “RELAXATION BECOMES SECOND NATURE and STRESS BECOMES A FAINT MEMORY” (265). For Wallace, “these promises point to the third kind of death-and-dread-transcendence the Nadir offers, one that required neither work nor play, the enticement that is a 7NC’s real carrot and stick” (265). This third type of promised transcendence seems to be one in which the cruisers are able to transcend the human condition altogether. They will eventually arrive at a place where they are no longer exhibiting normal human reactions to stimuli, for they will only be in a place of relaxation.

And, as Wallace witnesses, most passengers on the cruise are fooled into these fantasies of evasion and transcendence, as they sit relaxing surrounded by death and decay.


Though more of a style than a theme, Wallace’s humor in this piece is particularly sharp. There are countless instances of hilarity in the essay: everything from “I have tasted caviar and concurred with the little kid sitting next to me that it is: blucky” (258), to “I have seen nearly naked a lot of people I would prefer not to have seen nearly naked” (258). But more important than any actual examples of the humor (for when taken out of context they are not given justice), is just why and how Wallace is so funny. Marshall Boswell leads us in the right direction by explaining that the person Wallace creates in the essay “allows him to report on events with all the force of his formidable intellect while at the same time securing an amiable, self-effacing relationship with his readers” (Understanding David Foster Wallace 180). It is such a relationship that creates the perfect venue for Wallace’s humor. His wit and hilarity is written conversationally, making the reader feel as though Wallace is next to him whispering funny observations in his ear. The familiarity cultivated by Wallace’s persona creates a friendship between narrator and reader that heightens the connection to Wallace himself. This friendship allows for the reader to feel as though he has some stake in Wallace’s well-being, ultimately making Wallace’s jokes come alive.


Wallace’s semi-agoraphobia, while probably sincere, could act as a convenient excuse for not associating with the herd he so despises. He writes: “I'd have to sort of psych myself up to leave the cabin and go accumulate experiences, and then pretty quickly out there in the general population my will would break and I’d find some sort of excuse to scuttle back to 1009” (297 fn 55).

Return to the Womb

In this essay, Wallace seems to partially absolve the ship of its evils because of the sea’s calming affect. People sleep well: “in heavy seas you feel rocked to sleep, with the windows’ spume a gentle shushing, the engines’ throb a mother’s pulse” (285). On the ship they feel safe, contained, cared for, as if they were in a womb. However, the shadow of ‘death dread’ hangs decisively over his experience. The pairing of these two mimics the way a mother connects her child to death and birth (a theme also present in "Infinite Jest").


Some criticism this essay has been subjected to is that though Wallace’s characterization of cruise life is entirely satiric, humorous, and aimed to entertain, it is also saturated with hypocritical remarks, and characterizations that leave one with a bad taste in one’s mouth.

His descriptions of the Nadir itself and the culture surrounding it is very much in keeping with the experience one might have on a cruise ship; however, he consistently describes these situations in a negative light that touches upon condescension. This absurdity is more than possibly inherent in the nature of his journalistic observation.

In the essay, Wallace assumes the position of a journalist, constantly scanning his surroundings and succeeding in taking a significant amount of detail. As he watches the passengers on the dock in Cozumel he writes, “As each person’s sandal hits the pier, a sociolinguistic transformation from cruiser to tourist is effected” (308). He then goes on to show what seems to be feigned empathy, saying “Looking down from a great height at your countrymen waddling in expensive sandals into poverty-stricken ports is not one of the funner moments of a 7NC Luxury cruise” (310). He manages to point out the disgustingly exploitative relationship that is tourism, but still he is writing all of this as he participates within the system that he mocks. His negativity offers criticism that’s on point, but he describes all of this with an air of detachedness, as he metaphorically looks down on the sea of tourists.

He continues on to describe the interaction between the cruisers and Mexicans, saying, “I cannot help imagining us as we appear to them” (310). This line in particular appears as if Wallace is actually being genuinely empathetic and denouncing the Americanness that he finds unpleasant. However, his consistently sardonic commentary is tainted by perception of these moments where Wallace is actually breaking free past the faux-wood confines of the Nadir, and is seen touching upon significant problems in human relations. As he starts to empathize, it is impossible not to dwell upon how the relationship of tourism mirrors the job that paid Wallace to board this cruise and led him to exploit his fellow participants. Both the tourists and Wallace share in the act of approaching an Other and using its resources in order to inform, and essentially further the Self. Though these end goals are different, Wallace and the tourists share in this exploitative practice. In the end though, Wallace is seen as above it all.