Book Review: A Supposedly Fun Thing I'll Never Do Again

Originally Submitted to the Astral Codex Ten Book Review Contest

In March of 2020, when cruise stocks plummeted, and so many predicted the impending death or decay of the whole industry, I bought them all up, wildly, like without regard for the doomsaying soothsayers, not because of profit/cost ratios, technical analyses, or sober assessments of liquid cash reserves, but because of a piece of well-regarded literary journalism from the 1990s, an 100-page review/recollection/hallucination of a 7-day tropical cruise by a man who was then and remains, in death,  “one of his generation’s pre-eminent talents” and who is almost certainly one of about three American fiction writers of the last thirty years with a name that carries the world-historical ‘oomph’ of a Hemingway, Faulkner, or Pynchon.

The writer, of course,  is David Foster Wallace, and the essay ‘A Supposedly Fun Thing I’ll Never Do Again’, originally published by Harper’s Magazine in 1996 under the rather more uninspired ‘Shipping Out’. It has since become one of the most widely praised essays in the American canon, up there, kind of amazingly, with stuff like Didion’s ‘The White Album’ and Baldwin’s ‘Notes of a Native Son’ not only because it is funny and clever and full of approachable little philosophical tidbits like

An ad that pretends to be art is—at absolute best—like somebody who smiles warmly at you, only because he wants something from you. 

but because it takes as it’s subject the modern conception of “fun” as risk-free, guilt-free, duty-free period of pampering meant to resemble as close as possible the antenatal condition of choice-less bliss. The concept is reified and perfected in the form of a 7-day luxury cruise upon the MV Zenith. Said cruise fortuitously forces DFW to scramble for clear internal positions in regard to several items of pretty grand import including but not limited to: the ocean as endless primordial abyss, skeet-shooting, his own terror of death, professional smiles,  and shuffleboard. And there is perhaps no better passage to display the essay’s particular merits than the one on good old, septuagenarian-approved shuffleboard: 

Organized shuffleboard has always filled me with dread. Everything about it suggests infirm senescence and death: it’s a game played on the skin of a void, and the rasp of the sliding puck is the sound of that skin getting abraded away bit by bit. 

The only trouble is that it’s a prestige magazine piece and so by the time he’s spat out one Sartre-by-way-of-Larry-David style gem, he’s already moved on to the next, with little time to unpack each existentially panicked observation. I shudder at the thought of how many such tidbits were cut out for the sake of journalistic brevity—by DFW’s own report, during the cruise he ‘filled almost three Mead notebooks trying to figure out whether it was Them or Just Me.” 

An extremely callous devil’s advocate might say, “It was obviously you, DFW. You were admitted into psych-wards on multiple occasions for clinical, near-catatonic depression, and committed suicide in 2007. Meanwhile, the worldwide cruise industry has gone from serving a meager 4,970,000 people the year you cruised, 1995, to pampering 27,508,900 in 2019! So clearly it was Just You.”

Meanwhile I, DFW, and the text of the essay itself might humbly suggest this growth is not proof that DFW cruise-caused neurosis were incidental more to his mental illness than the experience itself,  but rather, the exact opposite. In fact, it’s the explosion in popularity not just in cruising, but every choice-less pampering-adjacent style of “fun” that has rendered the essay not just timeless and funny, but extremely, improbably, important.

Yet at the outset the essay is merely an amusing recollection of a ridiculously tame tropical vacation. DFW begins with a multi-paragraph list of sensory data, all shot-through with an attitude that more than snarky or cynical, is awed, even seemingly humbled by the sheer novelty of what’s occurred: 

I now understand the term “Duty Free.” 

I now know the maximum cruising speed of a cruise ship in knots. I have had escargot, duck, Baked Alaska, salmon w/ fennel, a marzipan pelican, and an omelette made with what were alleged to be trace amounts of Etruscan truffle. I have heard people in deck chairs say in all earnestness that it’s the humdity rather than the heat. I have been—thoroughly, professionally, and as promised beforehand—pampered. I have, in dark moods, viewed and logged every type of erythema, keratinosis, pre-melanomic lesion, liver spot, eczema, wart, papular cyst, potbelly, femoral cellulite, varicosity, collagen and sillicone enhancement, bad tint, hair transplants that have not taken—i.e. I have seen nearly naked a lot of people I would prefer not to have seen nearly naked. I have felt as bleak as I’ve felt since puberty…

And on and on in monotonous verbal orbit around the real focus of the essay, which is of course that very bleakness and it’s resultant death-consciousness, and their origins in that rich, equally monotonous period of non-stop pampering aboard the cruise. And it’s really not a subtle thing, this bleakness. It’s right there on page five, right after DFW’s assertion that the constant repetition of the word ‘pamper’ in the cruise line’s promotional material is in no way an accident—said material is attempting to draw a subliminal parallel between their product and that of the famed diaper brand. He then states, in plain terms: 

There is something about a mass-market Luxury Cruise that’s unbearably sad. Like most unbearably sad things, it seems incredibly elusive and complex in its causes and simple in its effect: on board the Nadir—especially at night, when all the ship’s structured fun and reassurances and gaiety-noise ceased—I felt despair. The word’s overused and banalified now, despair, but it’s a serious word and I’m using it seriously. For me it denotes a dimple admixture—a weird yearning for death combined with a crushing sense of my own smallness and futility that presents as a fear of death. It’s maybe close to what people call dread or angst. But it’s not these things, quite. 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. 

The object in question (which is still ferrying cruisers around in circuitous loops to this very day.)

And there is something extremely cathartic about reading a neurotic person’s pained processing of something so superficially mild as a luxury cruise. That, more than anything else, is the reason this essay has remained popular. All of us have trouble enjoying our vacations, but we manage to suppress those feelings in the name of getting our money’s worth. DFW is one who not only could not suppress such feelings but was in fact incentivized to expound upon them, to fill up notebooks with them inside his clean little cabin. This is an invaluable service to we, the reading public, best explained by a metaphor he uses in another essay to describe his undergraduate students collective inability to appreciate Kafka: 

We all know that there is no quicker way to empty a joke of its peculiar magic than to try to explain it—to point out, for example that Lou Costello is mistaking the proper name ‘Who’ for the interrogative pronoun ‘who’, and so on…Kafka of course, would be in a unique position to appreciate the irony of submitting his short stories to this kind of high-efficiency critical machine, the literary equivalent of tearing the petals off and grinding them up and running the goo through a spectrometer to explain why a rose smells so pretty. 

Replace ‘joke’ with ‘hedonistic experience’ and it becomes an apt description of DFW’s own process of reportage; he dissects common pleasurable experiences, primarily though investigations into why we find them pleasurable, by way of exploring why he fails  find them pleasurable. Because to DFW the cruise is nothing short of torturous, psychologically, but for a few bright moments, such as his interactions with the essay’s Dostoyevskian idiot and foil to atheistic and lost DFW, Tibor. Tibor the waiter shines with the particular brilliance competent, content, and healthily-resigned-to-reality people always do to the neurotic, and I find myself sharing the same profound admiration for him as DFW: 

He is 35 and about 5’ 4’’ and plump, and his movements have the bird-like economy characteristic of small plump graceful men. Menu-wise, Tibor advises and recommends, but without the hauteur that’s always made me hate the gastropedantic waiters in classy restaurants. Tibor is omnipresent without being unctuous or oppressive; he is kind and warm and fun. I sort of love him…Tibor was circling the table and asking each of us how our entree was, and we all regarded this as just one of those perfunctory waiter-questions and all perfunctorily smiled and cleared our mouths and said Fine, Fine—and Tibor finally stopped and he looked down at us all with a pained expression and changed his timbre slightly so it was clear that he was addressing the whole table: “Please. I ask each: is excellent? Please. If excellent, you say, and I am happy. If not excellent, please do not say excellent. Let me fix. Please.” 

The careful reader of this essay will notice that Tibor is just about the only non-pathetic passenger or employee aboard, the only one you don’t end up feeling sorry for. DFW’s tendency to portray all of humanity as kind of dithering, lost, and sad is so pronounced he even exaggerates the tendency into a verbal tick, wherein just about everyone is christened ‘Poor old X’ as convenient short hand for ‘here we have yet another example of endlessly fallible, petty, decaying human stock’ or else ‘Good Old X’ for ‘here we have same but of a kind with familiar and admirable qualities’. The amount of pity he’s able to wrench out of me as a reader is rather incredible. I’ve never felt such strong empathy for a run-of-the mill American twenty-something as with Winston, DFW’s sometime table tennis partner: 

As with good old Tibor, I don’t probe Winston in any serious journalistic way, although in this case it’s not so much because I fear getting [him] in trouble as because (nothing against good old Winston personally) he’s not exactly the brightest bulb in the ship’s intellectual chandelier, if you get my drift. E.g. Winston’s favorite witticism when deejaying in the Scorpio Disco is to muff or spoonerize some simple expression then laugh and slap himself in the head and go “Easy for me to say!” …he’s also unpopular with the younger crowd at the Scorpio Disco because he always wants to play Top-40ish homogenized rap instead of real vintage disco…[he] also sometimes seemed to suffer from the verbal delusion that he was an urban black male; I have no idea what the story is on this or what conclusions to draw from it. 

Nearly everyone DFW encounters is at least this pitiful and loathsome. There’s the mother of a 9-year-old chess prodigy who hovers over her daughter and DFW’s game hawkishly, and the spoiled teenager who takes one hundred dollars from her grandparents every night and never says thank you; there is also Mona, the girl at DFW’s table who speaks only of her deadbeat, parasitic boyfriend with whom she is infatuated, and at the center of it all of course, is pitiable DFW himself: 

As a kind of semi-agoraphobe who spends massive amounts of time in my cabin, I come to have a really complex dependency/shame relation with Cabin Service…I am kind of a slob, and I’m in Cabin 1009 a lot, and I also come and go a lot, and when I’m in here in 1009 I sit in bed and write in bed while eating fruit and generally mess up the bed. 

There is a way in which this essay can be read as a piece of near-future dystopian science fiction. The trouble is, it all really happened, more than twenty years ago, and so the mind reels at what cruising must be like in the age of the internet and the iPhone. And thus my mind did reel when I cruised in 2019, just a few months before cruising became an impossibility. Shamefully, I managed, like most good cruisers, to ignore my(and DFW’s, as I’d already read the essay) high-minded objections to such indulgence, and merely eat a lot of almost-great food and enjoyed seven better-than-average sunsets. Yet by the last couple of days the despair had wormed it’s way in, and I very much wanted to get off and go home. I was tired of my room being clean and the food being free and everything being just a short walk away. On the face of it, I felt bored, and the law of diminishing returns quickly worked it’s magic on every piece of steak I ate, every friendly chat with a stranger I initiated—by the end I despised how little any of it would or could matter, even on the meager scale a week of living can be measured. I felt the cruise was a simulacrum of something, but I was too full of food and drink to decide what. Luckily, DFW did so for me, much in the same way the cruise staff cracked open my lobster shells and peppered my salads(one could argue readers of DFW are philosophically pampered, even hand held through the entertaining tidbits between moments of great insight. There’s no one else I enjoy reading so much, and in a sense that scares me). He humbly submits that the cruise, in it’s looking after your every need, is a simulation of having people around who love you and care about you. This seems obvious on the face of it. One could put that description beside ‘western standards of professional hospitality’ in some strange cultural dictionary. Yet in it’s particulars, DFW’s point suggests the devastating consequences of what is basically an endless procession of hollow, cynical gestures of faked care: 

I submit that there’s something deeply mind-fucking about the Type-A-personality service and pampering on the Nadir, and that the manic invisible cabin-cleaning provides the clearest example of what’s creepy about it. Because, deep down, it’s not really like having a mom. Pace the guilt and nagging, etc., a mom cleans up after you largely because she loves you—you are the point, the object of the cleaning somehow. On the Nadir, though, once the novelty and convenience have worn off, I begin to see that the phenomenal cleaning really has nothing to do with me…it’s been particularly traumatic for me to realize that Petra is cleaning Cabin 1009 phenomenally well simply because she’s under orders to do so…I mean, 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 and significant value is all this indulgence and cleaning…since the ultimate point and object of the cleaning isn’t you but rather cleanliness and order, it’s going to be a relief for her when you leave. Meaning her hygienic pampering of you is actually evidence that she doesn’t want you around. The Nadir doesn’t have the Scotchguarded carpet or plastic-wrapped furniture of a true anal-type host like this, but the psychic aura’s the same, and so’s the projected relief of getting out. 

Yet he does not get out, even when given the chance during the ship’s frequent dockings. This is less due to the semi-agoraphobia as the fairly commonplace high-conscientiousness desire to not be among the gibbering masses of tourists who tour only in the most bland and touristic of places, where locals leer at you with mild disdain. He notes, quite correctly, that “there is something inescapably bovine about an American tourist in motion as part of a group. A certain greedy placidity about them,” and he finds the concept of joining such a group unappetizing, embarrassing even. The sad part about this, is that he accepts what he sees as destiny, something inescapable: 

A further self-esteem-lowerer is how bored all the locals look when they’re dealing with U.S. tourists. We bore them. Boring somebody seems way worse than offending or disgusting him. 

Yet in reality, the slightest modicum of effort can upgrade you in the eyes of locals from yet another tourist to a living breathing human being in mere seconds. A few words of local language, a simple joke, a trip down a path less taken, and the bovine herd is irrelevant, and you are not just another tourist but an individual, capable of forming a relationship with the novel locals and environment beyond simple observer-observed and customer-seller. 

DFW admits that he’d hardly left the country before at time of writing, and it shows both in his tendency to label things like the bovine herds of tourists and love of lowbrow mass-market entertainment as uniquely American, and his inability to discern that travel and enjoyment of exotic locals is a skill much like other skills, one that most tourists simply don’t possess. One of the most tragic aspects of DFW’s early death is that a writer as great as he never traveled far and wide enough to understand that almost everything he viewed as problematic in American culture was and is far more universal than he ever dared dream. What would he have had to say about African teenagers, less than a generation removed from grinding poverty, and still living in small villages, scrolling on their smartphones and receiving algorithmic indoctrination into the manners and mores of the West? We’ll never know, and instead we’re left only with the glib observation that Caribbean trinket-sellers are bored with American trinket buyers, and do not attempt to hide that fact. The fact that this might seem interesting to the swanky east-coast magazine readers DFW was writing for speaks to one thing that is almost uniquely American, at least in it’s level of intensity: the incredible insularity of cultural focus, and the belief that the American experience is primary and default as opposed to all others. Thus far, I’ve seen the strength of this implicit belief in primacy and importance matched only in Japan, which was literally closed off for 220 years and so has an obvious explanation. That it wouldn’t of occurred to poor old DFW and swanky east-coast magazine readers that American tourists aren’t inherently interesting is more than a little sad. I don’t mean to harp on this point, but it’s a constant refrain not just in this essay, but all of DFW’s writing. What seems on the surface to be self-deprecation is in fact reinforcement in this belief in American primacy: 

…the source of all the dissatisfactions [with cruise service] isn’t the Nadir at all but rather plain old humanly conscious me, or, more precisely, that 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. 

This section, delusions of self-deprecating American exceptionalism aside, brings us to the essay’s main point, which is essentially an analysis of the contrast between what the cruise brochure promises, and what the experience actually delivers: 

…the promise to sate the part of me that always and only WANTS—is the central fantasy the brochure is selling. The thing is to notice that the real fantasy here isn’t that this promise will be kept, but that such a promise is keepable at all. This is a big one, this lie. And of course I want to believe it—fuck the Buddha—I want to believe that maybe this Ultimate Fantasy vacation will be enough pampering…but the Infantile part of me is insatiable—in fact it’s whole essence or dasein or whatever lies in its a priori insatiability. 

Yet DFW admits elsewhere that the others are enjoying themselves, have managed to turn off the parts of their mind that prevent even momentary sensation of satiation. He likewise admits he has no idea how they do it, and fails to receive any real answer as to how he might achieve it himself. But of course there is a grand metaphor at the end of the essay, an image that contains the whole—DFW is sitting in the crowd before a famous British hypnotist, the week’s final and climactic piece of literally mind-numbing entertainment—and he is resisting with all his might. He cites a particular susceptibility to hypnosis as the reason, and so white knuckles his way through by a self-willed detachment that is itself a form of hypnosis: 

…I find myself, in my comfortable navy-blue seat, going farther and farther away inside my head…pulling mentally back, seeing the hypnotist and subjects and audience and Celebrity Show Lounge and deck and then whole motorized vessel itself with the eyes of someone not aboard, visualizing the m.v. Nadir at night, right at this moment, steaming north at 21.4 knots…hearing muffled laughter and music and [the club’s] muffled throb and the hiss of receding wake and seeing, from the perspective of this nighttime sea, the good old Nadir complexly aglow, angelically white, lit up from within, festive, imperial, palatial…yes, this: like a palace: it would look like a kind of floating palace, majestic and terrible, to any poor soul our here on the ocean at night, alone in a dinghy, or not even in a dinghy but simply and terribly floating, a man overboard, treading water, out of sight of all land. 

But crucially, the essay doesn’t end here, with an almost Lovecraftian image of mammoth, bone-white pleasure palace upon the high seas, throbbing with the power of what tools it uses to keep it’s prisoners enraptured. He continues right past this image, and gives us a strangely happy ending: 

This deep and creative visual trance—[the hypnotist’s] true and accidental gift to me—lasted all through the next day and night, which period I spent entirely in Cabin 1009, in bed, mostly looking out the spotless porthole, with trays and various rinds all around me, feeling maybe a little bit glassy-eyed but mostly good—good to be on the Nadir and good soon to be off, good that I had survived (in a way) being pampered to death (in a way)—and so I stayed in bed. And even though the tranced stasis caused me to miss the final night’s climactic P.T.S. and the Farewell Midnight Buffet and then Saturday’s docking and a chance to have my After photo taken with Captain G. Panagiotakis, subsequent reentry into the adult demands of landlocked real-world life wasn’t nearly as bad as a week of Absolutely Nothing had led me to fear. 

Our hero, having comforted himself with the alienation borne of his image of the ship’s exterior grandiosity, ostensibly sails off into the sunset and enjoys the afterglow of not just this cruise but of having recently completed the most important novel of the 90s, good old Infinite Jest. It’s then up for we, the readers, to make sense of what he’s undergone, to try and understand how much of it was him, and how much of it was Them, and if the vivid neuroses of this talented gen-xer mean anything much, in the grand scheme of things. 

At the risk of seeming to use the same trick twice, I want to use an image from the essay to illustrate the questionable import of DFW’s writings. Because he is in many ways a controversial writer. A great many well-educated people roll their eyes at the esteem and ‘status’ DFW, and especially Infinite Jest have received. There is also the infamous quote from literary critic Harold Bloom: 

You know, I don't want to be offensive. But 'Infinite Jest' is just awful. It seems ridiculous to have to say it. He can't think, he can't write. There's no discernible talent.

Though I’m wont to dismiss this as the casual dismissal of an old curmudgeon who simply refuses to give a young and trendy writer his due, I can’t help but see a kernel of truth in it. To a critic who saw Dante and Shakespeare as the beating heart of all past and future literary achievement, I can see how DFW’s writing could come off as mere hand-wringing, the vain navel-gazing of a virtuosic undergraduate that has gained praise merely because it has been pushed to it’s absolute limit in both verbosity and vulgarity. But that is more the aesthetic of Wallace than the core of him; he aimed to relentlessly entertain and enthrall through complex configurations of plot, character, and form, whilst imparting, or at least suggesting, moral imperatives with the confidence and power of the old Russian greats. And thus his description of his female tablemates’ laughs serves a metaphor for his own work’s difficult-to-pin-down significance: 

One of the reasons I liked all these women (except Mona) so much was because they laughed really hard at my jokes, even lame or very obscure jokes; although they all had this curious way of laughing where they sort of screamed before they laughed, I mean really and discernibly screamed, so that for one excruciating second you could never tell whether they were getting ready to laugh or whether they were seeing something hideous and scream-worthy over your shoulder…

This, the early 21st century, is the excruciating moment, and DFW’s work the scream. In dismissal of his work as pretentious, or his fears as misplaced, I detect the same impulse as what is in work in us when we dismiss real concerns over youngsters and their iPhones as stodgy and pointless. Collectively, we are unsure if there is something behind our shoulders, some horrible unforeseen price to be paid for the ever accelerating race towards low-risk, low-investment hedonism, and the universal pampering to our needs not just as consumers of food and drink, but of novelty, insipid social interactions, and status games. 

Or perhaps his work is just a scream of a different kind, a tick particular to his psychological make up, possessing little significance for those who hear it. But from where I sit, the individual experiences of people in wealthy nations resemble DFW’s cruisers more and more, and the lines are quickly being drawn between those, who like DFW, cannot suppress their discomfort at indulging in easy pleasures, and those who, like the happy voyagers aboard the Nadir, learn to ignore the resonant knock of hollow things, and instead relax into the pampering, making sure to get their money’s worth. 

Seen in this light, DFW was the beginning of a significant reactionary movement, one that was then merely his own feelings of disgust and confusion for a world fast becoming nothing but a space within which people move from one pleasure-conduit to another. But this movement now encompasses an explicitly political self-help movement wherein people do ‘dopamine detoxes’ become ‘digital minimalists’ or even, god forbid, honest-to-god religious people for whom this whole thing has become an actual holy war between ‘degenerates’ and the ‘based’ with no less than the fate of western civilization at stake. 

But no matter the degree one believes there is any real conflict going on at all, it’s still tempting to see DFW as a kind of particularly farsighted scout, who left behind copious, obsessively detailed notes about what loomed on the horizon, and then quietly departed the battlefield before things got really hairy. This humble cruise essay is not only one of the best and most illuminating of his field reports, but also, and I truly believe this, one of those pieces that will be honored, in the way someone like Montaigne or Shakespeare is honored today, by people three-hundred years from now who will look back on and declare DFW’s cruise essay as ‘one of the first truly modern pieces of writing’. Whether or not this is a good thing, is of course determined by our own relationship to pleasure, and to what degree we believe the world should be designed to provide it to us.