In his famous story, “A Supposedly Fun Thing I’ll Never Do Again,” originally published by Harper’s magazine in 1996, David Foster Wallace, the ridiculously gifted writer who committed suicide last fall at the age of 46, detailed his experiences as a passenger on a weeklong Caribbean cruise, combining flurries of facts and keen observations about the ship’s travelers, crew, food, entertainment, etc., with piercing analysis and deep reflection on what it means to be pampered and do “Absolutely Nothing” for seven days. The result is a masterful piece of non-fiction writing, full of humour, dread and deep insights. This morning, as I was reading the essay (originally titled “Shipping Out”), one of those insights struck me as being particularly relevant to magazines, so I thought I’d share it here.

Wallace spends the eighth section of “A Supposedly Fun Thing I’ll Never Do Again” deconstructing an “essay” by “famous writer and Iowa Writers Workshop Chairperson Frank Conroy” that appeared in the cruise ship brochure. Wallace objects to the essay on a number of grounds: its “tone of breathless approval,” its “constant and mesmeric references to fantasy and alternate realities and the palliative powers of pro pampering,” the way it tries to micromanage “not only one’s perceptions of a 7NC Luxury Cruise but even one’s own interpretation and articulation of those perceptions.” But mostly, Wallace objects to the “sneaky and duplicitous” way the brochure tries to present this blatant piece of advertising as editorial (or, as Wallace calls it, “art.”)

“Conroy’s ‘essay,’” Wallace writes, “appears as an insert, on skinnier pages and with different margins from the rest of the brochure, creating the impression that it has been excerpted from some large and objective thing Conroy wrote.” Of course, Conroy actually wrote the essay as a paid endorsement, but this isn’t acknowledge anywhere in the brochure.

The Canadian magazine industry has for years tried to fight against the unholy blending of “church and state.” We even have a set guidelines that magazines are encouraged to follow.  But occasionally—and particularly when times are bad—magazines will test the limits; in exchange for a quick buck, they’ll let ads slip onto covers, or into laundry room spreads, or onto transparent plastic overlays.

And then, when someone questions them on the ethics of it, the publishers and editors and salespeople who’ve crossed the line tend to shrug their shoulders and say something along the lines of, “It’s not a big deal.”

Here is Wallace’s argument for why it is a big deal. Feel free to supplant the word “essay” with “content” where appropriate:

Whether it honors them well or not, an essay’s fundamental obligations are supposed to be to the reader. The reader, on however unconscious a level, understands this, and thus tends to approach an essay with a relatively high level of openness and credulity. But a commercial is a very different animal. Advertisements have certain formal, legal obligations to truthfulness, but these are broad enough to allow for a great deal of rhetorical maneuvering in the fulfillment of an advertisement’s primary obligation, which is to serve the financial interest of its sponsor. Whatever attempts an advertisement makes to interest and appeal to its readers are not, finally, for the reader’s benefit. And the reader of an ad knows all this, too—that an ad’s appeal is by its very nature calculated—and this is part of why our state of receptivity is different, more guarded, when we get ready to read an ad.

In the case of Frank Conroy’s ‘essay,’ Celebrity Cruises is trying to position an ad in such a way that we come to it with the lowered guard and leading chin we properly reserve for coming to an essay, for something that is art (or that is at least trying to be art). 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. This is dishonest, but what’s sinister is the cumulative effect that such dishonesty has on us: since it offers a perfect facsimile or simulacrum of goodwill without goodwill’s real spirit, it messes with our heads and eventually starts upping our defenses even in cases of genuine smiles and real art and true goodwill. It makes us feel confused and lonely and impotent and angry and scared. It causes despair.