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The Importance of Being Earnest

David Foster Wallace was the voice of his generation, for better and for worse.

The Pale King
By David Foster Wallace
(Little, Brown, 548 pp., $27.99)

Fate, Time, and Language: An Essay on Free Will
By David Foster Wallace
(Columbia University Press, 252 pp., $19.95)

Although Of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace
By David Lipsky
(Broadway Books, 320 pp., $16.99)

Today we think of the 1920s as a golden age of American fiction. But to Edmund Wilson, looking back in 1944, the most striking thing about this modern generation, which he did more than any critic to foster, was its failure to reach full development. The best writers of the 1920s, he wrote in “Thoughts on Being Bibliographed,” had either “died prematurely ... leaving a sad sense of work uncompleted,” like F. Scott Fitzgerald and Sherwood Anderson, or “disconcertingly abandoned their own standards”—here the unnamed culprit is surely Ernest Hemingway, whom Wilson had helped to discover. For us, of course, these are all canonical names, predestined for Library-of-America cursive. So it is helpfully disconcerting to learn that, for Wilson, they seemed to have been canonized too soon: “men of still-maturing abilities, on the verge of more important things, have turned up suddenly in the role of old masters with the best of their achievement behind them.”

At the time Wilson wrote, this particular style of American literary martyrdom was on the verge of obsolescence. After the war, as the center of cultural gravity moved from London and Paris to New York, and the American university and publishing establishments began their dramatic expansion, the situation of the American writer became very different, and in most material respects much better. Consider the major American novelists who emerged in the 1950s—Bellow, Updike, Mailer. All enjoyed longevity, consistent productivity, and public honor; the disorder of their personal lives was chronic and in some ways stimulating, rather than acute and lethal. In these respects they differed markedly from the great writers of the 1920s. And today’s leading writers, who are more dependent on the academy for sustenance, seem still further from the old, prodigal, unhappy American career.

Except for David Foster Wallace. He was exceptional in many ways—in the scale of his ambition and achievement, the affection he inspired in readers, the generational significance of his life and death. But the root of Wallace’s distinction may have been his untimely style of Americanness. Like Anderson, Wallace presented himself as a sensitive man at odds with a crass commercial society. Like Fitzgerald, he was a collegiate prodigy (his first novel, The Broom of the System, started as a fiction thesis at Amherst) who achieved fame as the voice of an era. Like Hemingway, he was deeply concerned with traditional manliness, and with the ethics of sports and games.

And like all of those writers of an earlier day, Wallace was a self-conscious son of the Midwest. He grew up in Urbana-Champaign, the son of a philosophy professor at the University of Illinois, but he did not see himself as part of a relatively placeless academic caste. Instead, he keenly embraced his origins in America’s physical and metaphorical “heartland,” and he wrote with a certain trepidation about the big cities of the East. In “A Supposedly Fun Thing I’ll Never Do Again,” his celebrated essay about taking a luxury cruise, he offhandedly mentions “the way we find even very basic human decency moving if we encounter it in NYC or Boston.”

Wallace acknowledged that it was partly the ethnic and racial diversity of the metropolis that made it seem alien to him. “For me, public places on the U.S. East Coast are full of these nasty little moments of racist observation and then internal P.C. backlash,” he wrote. As a writer who went to college and entered the literary world in the 1980s, during the first flush of multiculturalism and political correctness, Wallace was highly aware of his ambiguous status as a white male. “If all blacks are great dancers and athletes, and all Orientals are smart and identical and industrious, and all Jews are great makers of money and literature, wielders of a clout born of cohesion, and all Latins are great lovers and stiletto-wielders and slippers-past-borders—well then gee, what does that make all plain old American WASPs?” he asks, only half jokingly, in “Westward the Course of Empire Takes Its Way,” an early story.

That title is itself half a joke, borrowed from Berkeley’s poem. But the story—which enacts a complicated homage to and rebellion against John Barth’s metafictional classic Lost in the Funhouse—takes its directional symbolism seriously. Barth lives in and often writes about the Maryland tidewater country, on America’s eastern rim. Wallace’s story, which describes a group of writing students visiting rural Illinois, explicitly casts the journey west as a movement away from Eastern complexity and metafictional jadedness, toward a new birth of naïveté and emotional directness. Almost from the beginning, Wallace saw himself as a spokesman for “the forward simplicity of a generation for whom whatever lies behind lies there fouled, soiled, used up. East.” Hemingway’s Nick Adams, recuperating from war by going fishing on the Big Two-Hearted River, or Fitzgerald’s Nick Carraway, returning to “my Middle West” after his corrupting sojourn among the Buchanans and Wolfsheims, would have understood Wallace perfectly.

Certainly, the body of work that Wallace left behind is open to the criticism that Wilson leveled at those writers—it is precocious, very uneven, at times immature. And Wallace’s death by suicide in 2008, at the age of forty-six, has sealed him forever in the catalog of tragic and “premature” American writers. Yet with Wallace, too, the faults of his work seem inseparable from the virtues. A more disciplined, tactful writer would not have published a thousand pages of Infinite Jest, with all its shaggy-dog repetitions and manic elaborations and half-baked jokes. But then, a shapely, four-hundred-page version of Infinite Jest would not have been a cultural sensation or a generational landmark.

Some intelligent readers have declared themselves simply allergic to Wallace’s style, unable to cope with all the mannerisms and acronyms and footnotes, the boyish self-conscious earnestness, the sentences that start “And but so now” or “The improbable thing of the whole thing is that.” And it is true that Wallace’s style is so stylized that it teeters on the edge of self-parody, like Hemingway’s. Yet in a story such as “The Depressed Person,” which even at thirty pages seems very long, the feeling of excess, of being trapped in a room with a very intelligent obsessive-compulsive, is exactly the sensation that Wallace wanted to convey. With Wallace, waste is of the essence of the scheme.

THE MOST AMERICAN thing about Wallace, though, is his conviction that his unhappiness is a specifically American condition. Like many classic American writers but few contemporary ones, he experienced being American as a bitter and significant fate, a problem that the writer had to unravel for the benefit of his fellow sufferers. In a late story, “The Suffering Channel,” Wallace theorizes about “the single great informing conflict of the American psyche,” which is “the conflict between the subjective centrality of our own lives versus our awareness of its objective insignificance.” All of Infinite Jest can be seen as a demonstration of the thesis Wallace advances early in the novel: “American experience seems to suggest that people are virtually unlimited in their need to give themselves away, on various levels.”

When Wallace wrote about how difficult it was to be an American, he specifically meant an American of his own generation—the post-’60s cohort known as Generation X. “Like most North Americans of his generation,” Wallace writes about the teenage hero of Infinite Jest, “Hal tends to know way less about why he feels certain ways about the objects and pursuits he’s devoted to than he does about the objects and pursuits themselves.” Likewise, in “Westward,” he observes, “Like many Americans of his generation in this awkwardest of post-Imperial decades ... Sternberg is deeply ambivalent about being embodied.” It is no wonder that readers born between 1965 and 1980 responded so strongly to this kind of solicitude, with its implication that they were unique, and uniquely burdened.

But what is really most American—and most Generation X—about these laments is their provincialism. For Wallace to find it plausible that “being embodied” or “objective insignificance” were new American problems is as sharp an indictment of American ignorance as those polls that are always showing that half of us cannot find the United States on a map. Except that if any young novelist knew the ancient history of such problems, it should have been Wallace. He was widely read, and he studied philosophy in college and graduate school; his first novel plays knowingly with Wittgenstein and Derrida. In the introduction to Fate, Time, and Language: An Essay on Free Will, the posthumous edition of Wallace’s senior thesis, his father remembers reading the Phaedo with his fourteen-year-old son: “This was the first time I realized what a phenomenal mind David had.”

This short book is both an homage to Wallace’s reputation as a philosophical novelist and an attempt to solidify it. As a senior at Amherst, while working on the fiction that would become The Broom of the System, Wallace also produced a philosophy thesis called “Richard Taylor’s ‘Fatalism’ and the Semantics of Physical Modality.” In challenging Taylor’s paper “Fatalism”—which is reproduced in the book, along with a number of other philosophers’ responses to it—Wallace set out to defend our common-sense intuition of free will. This sounds like a big, novelistically fertile subject, and in his introduction James Ryerson claims that Wallace’s early training in philosophy “would play a lasting role in his work and thought, including his ideas about the purpose and possibilities of fiction.”

In fact, what Fate, Time, and Language demonstrates is not the value of analytic philosophy for literature, but its dramatic inferiority to literature as a way of discussing the most existentially urgent problems. Wallace’s paper boils down to the statement that the future cannot be fixed before it happens, because it is the future and not the past. But to get to this point, he wends his way through spiny thickets of modus ponens and modus tollens, demonstrating a mastery of propositional logic so thorough as to make the idiom itself seem facile, even comic.

If there is a continuity between Wallace the undergraduate philosopher and Wallace the novelist, it is not in the profundity of his ideas, but in his perfect pitch for all kinds of jargon. One section heading in the paper reads, “A Formal Device for Representing and Explaining the Taylor Inequivalence: Features and Implications of the Intensional-Physical-Modality System J.” The same teasing relish for professional idioms finds its way into Wallace’s writing about pharmaceuticals in Infinite Jest, or about lexicography in the essay “Authority and American Usage,” or about the tax code in The Pale King, his unfinished posthumous book.

SO WALLACE’S SENSE that his own time and place are uniquely afflicted by loneliness and doubt and mortality cannot be ascribed to ignorance. But this only makes it even more significant. For then it must mean that the ways human beings have always addressed these subjects—through philosophy, religion, and literature—have simply lost their potency and reality for Wallace, and for the American generation that he represents.

There is a revealing exchange on this subject in Although of Course You End Up Becoming Yourself, a book-length transcript of an interview with Wallace conducted by David Lipsky in 1996. Wallace has been denigrating “conventional realistic” fiction, the way “it imposes an order and sense and ease of interpretation on experience that’s never there in real life.” Lipsky, who is also a novelist, cogently objects that “Tolstoy’s books come closer to the way life feels than anybody, and those books couldn’t be more conventional.” To which Wallace replies with a familiar litany: “Life now is completely different than the way it was then”; “some of it has to do with ... MTV videos”; “life seems to strobe on and off for me, and to barrage me with input”; “I received five hundred thousand discrete bits of information today.”

This kind of phenomenological presentism—this certainty about the unprecedented newness of one’s own experience—is itself very old by now, at least as old as modernism. But every generation seems fated to discover it again, and for Wallace it served a useful purpose. It made loneliness and despair not merely existential conditions, but timely “issues”; it allowed him to think of himself as a representative man and a social commentator. A whole strand of Wallace’s work is concerned with diagnosing the cultural causes of his generation’s alleged breakthrough in anomie.

In an influential essay called “E Unibus Pluram: Television and U.S. Culture,” he blames television—not simply because it physically isolates people and breaks down communal ties, but also for the way its massive, formulaic stupidity encourages intelligent viewers to develop a defensive irony. “Irony and ridicule are entertaining and effective,” Wallace observes, “and ... at the same time they are agents of a great despair and stasis in U.S. culture.”

This argument is translated into fictional terms in the early story “My Appearance,” from Wallace’s collection The Girl with Curious Hair, which appeared in 1989. The story concerns a middle-aged, moderately successful TV actress who is making an appearance on David Letterman’s talk show. Her challenge is to find a way to communicate sincerely in the face of Letterman’s sneering irony, which to Wallace is the epitome of TV-bred cynicism. A friend tells her that the only way to cope is to out-Letterman Letterman: “Laugh in a way that’s somehow deadpan. Act as if you knew from birth that everything is clichéd and hyped and empty and absurd, and that that’s just where the fun is.”

Wallace dreads this kind of irony, which poisons communication and makes displays of emotion look ridiculous. He dreads it on civic grounds, of course; but he also sees cool knowingness as a deadly threat to his own literary genius, which is essentially sentimental and melodramatic. (“There’s never been a time in serious art more hostile to melodrama,” he complained to Lipsky.) That is why Wallace is exercised by the ironic self-consciousness of postmodern fiction, in much the same way that he is disturbed by David Letterman. Lost in the Funhouse can hardly be held responsible for “a great stasis and despair in U.S. culture”—for one thing, not enough people have read it. But in “Westward,” Wallace offers a novella-length attack on the metafictional gamesmanship of Barth’s story: “You want to get laid by somebody that keeps saying ‘Here I am, laying you?’ Yes? No? No. Sure you don’t. I sure don’t. It’s a cold tease. No heart. Cruel. A story ought to lead you to bed with both hands.”

In his hostility to pop-cultural irony, Wallace was (ironically, perhaps) in agreement with the best pop culture of his time. Many people have observed that Wallace’s trademark look—the bandana, lank hair, and stubble that appear in his author photos, and made him one of the most recognizable writers of his time—evoked the grunge style of Kurt Cobain, the lead singer of Nirvana, whose suicide in 1994 was a mythic moment for Generation X. When Lipsky, who was profiling Wallace for Rolling Stone, asked him the obligatory questions about his taste in music, he described Cobain’s songs as “absolutely incredible. But unbelievably painful. I mean if you, you know, all the stuff that I was groping in a sorta clumsy way to say about our generation? Cobain found, Cobain found incredibly powerful upsetting ways to say the same thing.”

The famous lyrics of “Smells Like Teen Spirit”—“I feel stupid and contagious/Here we are now, entertain us”—could be used as an epigraph to Wallace’s essay on television, and even more appropriately to Infinite Jest. Cobain’s sullen parody of alienation used irony to defeat irony, much as Wallace, in “Westward,” used metafiction to defeat metafiction. And the young novelists who followed in Wallace’s wake—Jonathan Safran Foer, Dave Eggers, and Zadie Smith, to name the most prominent—have shared his righteous refusal of irony. They believe that literature should be positive, constructive, civically engaged, a weapon against alienation. Jonathan Franzen, who was Wallace’s close friend and has staked repeated public claims to his legacy, told The Paris Review that the two of them shared a philosophy of fiction: “The point of agreement that he and I eventually reached was the notion of loneliness: that fiction is a particularly effective way for strangers to connect across time and distance.”

In the fifteen years since Wallace published Infinite Jest, this sovereign sincerity, this earnest hostility to irony, has come to define the best younger writers, making them a distinctive literary generation—for both good and ill. It is necessary to insist, therefore, upon the value of irony, and its difference from apathy and despair. Irony can be an indispensable tool of resistance and critique. More, for a certain kind of writer—for Hawthorne, or Mann—an aristocratic irony is the only way of doing justice to the contradictions of our moral lives, of acknowledging that the impulse to sin and to desecrate is as deeply rooted in us as the impulse to help and build. A literary generation whose critical organ is called The Believer—with its implication that perfect faith should be taken at face value, unskeptically—and that expects every writer to be a literacy tutor, as if goodness is part of aesthetic achievement, has perhaps forgotten that literature is a calling in part because it is a daimon. But that is something that Wallace himself knew all too well.

WALLACE IS generally described as a cerebral and difficult writer, and sometimes thought of himself that way. Discussing Infinite Jest with Lipsky, he remarked that “I wanted to try to do something that was really hard and avant-garde, but that was fun enough so that it forced the reader to do the work that was required.” Yet as time passes, it becomes harder to see why that novel was ever considered very difficult or avant-garde. Yes, Wallace rotates through a few different narrators, and leaves some background information unclear, and uses some five-dollar words. But none of this requires more “work” than, say, a movie by David Lynch (whom Wallace admired very much). Certainly, the notorious length of Infinite Jest is not a gauntlet thrown to the reader. It feels, rather, like a return to the spaciousness of Dickens and Balzac, its bulk a product of repetition and detail and the multiplication of characters. These are all techniques of readerly seduction and immersion, ways of “leading you to bed with both hands.”

Infinite Jest is written on the pleasure principle: that is its strength and its weakness. Wallace’s sheer joy in writing is responsible for what he calls in the novel itself “the aleatory flutter of uncontrolled, metastatic growth.” It is full of catalogs, stories within stories, invented idioms, and elaborate anecdotes about characters who appear only once. His use of footnotes, one of the most recognizable elements of his style, is a way of making more room for irrelevant digressions, the way a hoarder might build a second story on his house.

One footnote in Infinite Jest offers the filmography of an invented director, listing dozens of movies that Wallace describes even though they never feature in the novel at all; it runs to eight pages of small print. Elsewhere in the novel Wallace describes a school party at which all the students are encouraged to wear funny hats. This is supplemented by a footnote listing the kind of funny hat worn by every attendee: “Troeltsch wears an InterLace Sports baseball cap, and Keith Freer a two-horned operatic Viking helmet along with his leather vest, and Fran Unwin a fez,” and so on. In the introduction to The Pale King, Michael Pietsch, Wallace’s editor at Little, Brown, mentions that he referred to his first drafts as “freewriting,” and this term perfectly captures the self-delighting excess of much of Infinite Jest.

Yet Infinite Jest is also an attack on the pleasure principle. The main plot concerns a movie that is so entertaining it reduces everyone who sees it to a catatonic stupor. Wallace offers several installments of a dialogue between a Québécois terrorist named Marathe, whose colleagues want to acquire the movie and use it as a weapon against the United States, and an American spy named Steeply, who is trying to outwit the terrorists and find the movie first. It is typical of the novel that this dialogue is at once totally slapstick—Steeply wears ill-fitting drag, Marathe speaks mangled Frenchified English, and the whole conversation takes place on a narrow ledge on a mountainside in the Arizona desert—and didactically earnest. Marathe argues that the only reason America fears “the Entertainment,” as it is called, is that the country has lost its will power, its character:

Now is what has happened when a people choose nothing over themselves to love, each one. A U.S.A. that would die—and let its children die, each one—for the so-called perfect Entertainment, this film. Who would die for this chance to be fed this death of pleasure with spoons ... can such a U.S.A. hope to survive for a much longer time? To survive as a nation of peoples? To much less exercise dominion over other nations of other peoples? If these are other peoples who still know what it is to choose? who will die for something larger?

This line of argument, comical as it is coming from a French Canadian—to an American, the very idea of a dangerous Canadian is a gag—sounds more formidable when it comes from, say, an Islamic jihadist. (Shortly after September 11, an Afghan mujahid was widely quoted as saying “the Americans love Pepsi Cola but we love death,” which is more or less Marathe’s point.) Wallace sharpens the indictment of American hedonism by setting half of Infinite Jest in the world of twelve-step programs and halfway houses. How much must Americans be suffering, Wallace asks, if they are willing to destroy their lives and embrace death in order to temporarily blot out consciousness?

The name of the movie that entertains to the point of killing is “Infinite Jest,” and Wallace means us to see the parallel between it and the novel, which is itself a literary overdose. Can reading—more to the point, can writing—be a kind of drug, a distraction from an otherwise insufferable existence? Is it possible to be addicted to writing? There is no avoiding the question in a book that is so knowledgeable and convincing about the dynamics of addiction—the way suffering leads to excess, which compounds suffering, until it is impossible either to go on taking Substances (Wallace’s term) or to stop. In Alcoholics Anonymous, Wallace insists, it is the most intelligent, articulate addicts who have it hardest: “They identify their whole selves with their head, and the Disease makes its command headquarters in the head.”

INEVITABLY, WE READ Wallace now with the knowledge that he committed suicide, after a lifelong struggle with depression. Talking to Lipsky, he took pains to hide the facts of his illness: “I’m not biochemically depressed,” he insisted, and specifically denied that he took antidepressants. In fact, according to posthumous reports, Wallace took the antidepressant Nardil for almost two decades, and it was his attempt to go off the drug that precipitated his final depression and suicide. But no reader of his fiction could have been convinced by Wallace’s denials. (Lipsky clearly was not.) There are just too many characters in his fiction who share the experience of Kate Gompert, from Infinite Jest, whom we first meet in a mental hospital after a suicide attempt: “I wanted to just stop being conscious ... I wanted to stop feeling this way.”

What would it be like to inhabit such a suffering consciousness, without muffling it in a thousand pages of voluble prose? Brief Interviews with Hideous Men, the book Wallace published after Infinite Jest, is his devastating answer. The book consists of a number of stories, interwoven with “transcripts” of the titular interviews, from which the questions have been deleted. Both stories and interviews show that Wallace’s truest subject as a writer, the one that provoked his most moving and convincing work, was the sickness of the will. Again and again, he creates characters who are intelligent enough to anticipate every one of their own thoughts and reactions, even the most destructive and dysfunctional, but who lack the will to change them. The maddening self-consciousness and hyper-articulacy that sometimes seem like mere tics of Wallace’s prose become, in Brief Interviews, the absolutely faithful reflection of a consciousness that knows itself too well, and is disgusted by what it knows.

The ultimate case study here is “The Depressed Person,” in which we see how a woman’s unbearable suffering—“depression’s terrible unceasing agony itself, an agony that was the overriding and unendurable reality of her every black minute on earth”—makes her unbearably self-obsessed. This, in turn, renders her deeply unsympathetic, not just to the friends who abandon her but also to herself, so that self-hatred is added to unhappiness. It is a spiral or Möbius strip of misery, a genuinely Dostoevskyan performance. Behind the Depressed Person we hear another eloquently damned soul, the Underground Man, who also suffers from the gap between reason and will, between knowing what’s wrong with you and being able to repair it.

“STANDARD THERAPY [is] such a waste of time for people like us—they thought that diagnosis was the same as cure. That if you knew why, you would stop. Which is bullshit.” So says Meredith Rand, one of the half-dozen IRS agents who emerge as major characters in the incomplete drafts and notes of Wallace’s last novel, now published as The Pale King. Other prominent voices in the plotless chorus include Lane Dean Jr., who takes a job at the IRS after getting his high school girlfriend pregnant; Claude Sylvanshine, a hapless underling whose career has stalled at a low pay grade; Toni Ware, whose violent childhood is narrated in a florid style that reads like a parody of Cormac McCarthy; and most significantly, Chris Fogle, who describes his work as an auditor as a kind of religious vocation.

And then there is “David Wallace” himself, who addresses us directly in a few passages. The Pale King was apparently meant to be cast as Wallace’s own “vocational memoir,” a description of the year he spent working for the IRS in the mid-1980s, after being suspended from college for running a term-paper mill. Of course, the real Wallace never worked for the IRS, and it is a little dispiriting to see him still toying with metafictional tricks—all the more so when he teasingly disavows those tricks even as he plays them: “Please know that I find these sorts of cute, self-referential paradoxes irksome too—at least now that I’m over thirty I do—and that the very last thing this book is is some kind of clever metafictional titty-pincher.” The awkwardness of the “David Wallace” passages in The Pale King are indicative of Wallace’s difficulty in finding the right way to frame his material. It seems clear from the book as we have it that Wallace chose the IRS as a subject without knowing quite how to write about it, or what stories he wanted to tell.

Why pick such an unpromising subject, and stick with it through years of frustration? (Pietsch writes that Wallace “described working on the ... novel as like wrestling sheets of balsa wood in a high wind.”) A clue to the answer can be found in a question that Wallace asked in Infinite Jest: “Why is the truth usually not just un- but anti-interesting?” In that excessively interesting book, the interesting is always suspect. Substances are interesting, the Entertainment is interesting, because they distract a mind that would otherwise tear itself apart; but they only distract, they do not really fulfill or heal.

As an alternative, in Infinite Jest, Wallace offers two images of genuine fulfillment: the athletic discipline of the young players at Enfield Tennis Academy (E.T.A.), and the spiritual surrender of the recovering addicts at Ennet House. In both cases, Wallace is explicit that the key to happiness is the relinquishing of consciousness. The AA slogan is “my best thinking got me here,” while at E.T.A., “the program ... is supposedly a progression toward self-forgetting,” in which the player abandons all thought of fame, concentrating solely on the game itself. In both cases, serenity comes not from the frenzied quest for new sources of stimulation, but from a quasi-Buddhist acceptance of everything that occurs. This is the nirvana attained by Don Gately, a recovering addict who is in the hospital for a gunshot wound but refuses to accept any kind of narcotic, lest he jeopardize his sobriety. In the novel’s last hundred pages, Gately overcomes his pain by recognizing that “everything unendurable was in the head, was the head not Abiding in the Present but hopping the wall and doing a recon and then returning with unendurable news you then somehow believed.”

But if the interesting is the delusive, addictive maya of this world, then the boring and the unpleasant is what is really real; and the token of mental wholeness, of adult sobriety, is the ability to cope with unrelieved boredom. That is why The Pale King had to be a novel about the IRS. For what is more boring and repellent than the tax code, or more notoriously inevitable? “The whole subject of tax policy and administration is dull. Massively, spectacularly dull,” says “David Wallace.” But he suggests that it would be a sign of weakness to ignore it simply because it is dull:

To me, at least in retrospect, the really interesting question is why dullness proves to be such a powerful impediment to attention.... Maybe dullness is associated with psychic pain because something that’s dull or opaque fails to provide enough stimulation to distract people from some other, deeper type of pain that is always there, if only in an ambient low-level way, and which most of us spend nearly all our time and energy trying to distract ourselves from feeling, or at least from feeling directly or with our full attention.

The Pale King is Wallace’s attempt to find out if fiction can sustain this kind of attention to boring, banal reality, without contracting into the solipsistic fugues of Brief Interviews or expanding into the manic inventions of Infinite Jest. In fact, Wallace only occasionally tries to make his book itself rebarbatively dull—to enact the boredom he writes about. There are several passages of tax jargon, and a long description of a traffic jam (which doubles down on dullness by turning into a discussion of the failure of the municipal bond issue that could have expanded the jammed road). Most notably, there is a three-page section, printed in double columns like a dictionary or a Bible, describing a room full of tax-form examiners at work: “Chris Fogle turns a page. Howard Cardwell turns a page. Ken Wax turns a page. Matt Redgate turns a page.” This is Wallace’s stab at evoking the routine that leads Lane Dean, for one, to think of his job as a foretaste of hell:

He felt in a position to say he knew now that hell had nothing to do with fires or frozen troops. Lock a fellow in a windowless room to perform rote tasks just tricky enough to make him have to think, but still rote, tasks involving numbers that connected to nothing he’d ever see or care about, a stack of tasks that never went down, and nail a clock to the wall where he can see it, and just leave the man there to his mind’s own devices.

Here Wallace seems to echo Pascal: “If a soldier or laborer complains of the hardship of his lot, set him to do nothing.” The putative relation of boredom to goodness is an old theme. Wallace’s sense that boredom is the emblematic ordeal and the hardest discipline of human existence puts him in a long line of religious thinkers and writers. “Teach us to care and not to care,/Teach us to sit still,” Eliot wrote: it could be Don Gately’s prayer, or Lane Dean’s.

A genuinely avant-garde or experimental writer might have tried to compose a whole novel out of those double columns. But Wallace was not that kind of writer. Too generous and warmhearted to torment the reader, what he really wanted was to delight and to instruct—above all, in his last years, to instruct. For The Pale King belongs to a series of late works in which Wallace was grappling with the idea of authority, and tentatively trying on the role of an authority figure. (How terrible to have to use the word “late” for things written in his early forties.)

In 2000, Wallace covered John McCain’s presidential campaign for Rolling Stone. The resulting essay—“Up, Simba!” in Consider the Lobster—celebrates a very traditional ideal of masculine stoicism and honor: “The fact is that John McCain is a genuine hero ... because of not what he did but what he suffered—voluntarily, for a Code. This gives him the moral authority both to utter lines about causes beyond self-interest and to expect us, even in this age of spin and lawyerly cunning, to believe he means them.” Wallace found a different kind of authority in Bryan A. Garner, whose Dictionary of Modern American Usage he writes about in “Authority and American Usage.” “America is in the midst of a protracted Crisis of Authority in matters of language,” he observes. But Garner, whose work Wallace praises inordinately, strikes him as a model of democratic authority, based not on coercion but on rational consent: “in the absence of unquestioned, capital-A Authority in language, the reader must now be moved or persuaded to grant a dictionary its authority, freely and for what appear to be good reasons.”

IN THE INTRODUCTION to Fate, Time and Language, James Ryerson suggests that Wallace was a philosophical novelist in the tradition of Voltaire and Sartre. Perhaps the best reason for denying this is that Wallace did not seem to recognize that the problem he had discovered was Kant’s problem, and that his solution was Kant’s solution. The only valid laws are the ones we legislate for ourselves, in accordance with the dictates of reason: this is the key to moral autonomy, and in The Pale King, it is the definition of adulthood.

In the words of Chris Fogle, the most important character in the book, “If I wanted to matter—even just to myself—I would have to be less free, by deciding to choose in some kind of definite way. Even if it was nothing more than an act of will.” Fogle’s story seems to express Wallace’s deepest intention in writing about the IRS, and his most heartfelt counsel to his readers. It is explicitly cast as a conversion testimony: once a layabout, a stoner, a self-described “wastoid,” Fogle is born again as a mature and disciplined adult, a worthy heir of the father he was always disappointing.

His moment of grace comes when he accidentally stumbles into an Advanced Tax course at his college, and hears what amounts to a sermon, from a professor whom Fogle believes is a Jesuit (though he turns out not to be). Punning broadly on the notions of “calling” and “accounting,” the teacher tells the students that they are “called to account.” The CPA is commercial society’s indispensable man, its quiet hero: “I wish to inform you that the accounting profession to which you aspire is, in fact, heroic ... Enduring tedium over real time in a confined space is what real courage is.”

Wallace peppers The Pale King with surreal invented details about the IRS, including its alleged Latin motto, “Alicui tamen faciendum est”—roughly, “Anyway, someone has to do it.” And in this book, the ones who step up, who attend to the tedious business of life, are defiantly archaic authority figures. They are Midwestern patriarchs, men in gray flannel suits (“like so many men of his generation, his body almost seemed designed to fill out and support a suit,” Fogle says about his father), and earnest Christians—types that seldom appear in pop culture (or literary fiction) except as figures of fun. In one section of The Pale King, Lane Dean decides not to pressure his girlfriend to get an abortion, but to marry her instead, even though he doesn’t love her. He makes this decision by asking, literally, what would Jesus do, and you can sense Wallace daring you to roll your eyes.

Such nostalgia for a vanished style of religious and patriarchal authority is a familiar part of conservative political discourse. And in The Pale King, Wallace takes obvious pleasure in rehearsing a number of conservative tropes, which he knows many readers will find provocative. Hostility to the 1960s has been a constant in his work, dating back to the early story “Lyndon,” in which he displayed a surprising sympathy for LBJ in his contest with anti-war protesters. In The Pale King, Chris Fogle’s mother is a victim of the 1960s: drunk on women’s lib, she impetuously divorces her dutiful husband, becomes a lesbian, and opens a feminist bookstore called Speculum Books with her lover, Joyce. Once Fogle’s father dies, however, she is consumed with remorse for her flightiness, and moves back into the marital home. In a vindictive touch, Joyce ends up getting married to a man and becoming a suburban housewife in Wilmette. (See what happens when consciousness-raising gets out of hand?)

Other characters in this polyphonic book say things like “the sixties were America’s starting to decline into decadence and selfish individualism—the Me generation,” and talk about the sacredness of the Constitution and the Federalist Papers. Even “David Wallace” describes the invention of rolling luggage carts as “the sort of abrupt ingenious advance that makes entrepreneurial capitalism such an exciting system—it gives people incentive to make things more efficient.” Meanwhile, the Advanced Tax instructor scoffs at Karl Marx’s vision of a society in which a man can “hunt in the morning, fish in the afternoon, rear cattle in the evening, criticize after dinner, just as I please.” Doing just what you please, for Wallace, is the fatal freedom that leads to anomie and despair.

The problem with Wallace’s conservatism of values, his cultural nostalgia, is not so much the sentiment behind it, which is genuine and partly admirable, as its danger of patness, and its edge of nastiness. Some passages of The Pale King do feel merely complacent; but others suggest that Wallace was aware of this danger, and intended to put his central conceit under some ironic pressure. To Chris Fogle, the IRS is “the Service,” and joining it is like joining the priesthood or the Marines. But “David Wallace,” who arrives at the Peoria office and is mistaken for a much higher-ranked IRS employee of the same name, gets to see that the Service is actually full of sinister bureaucratic slapstick, of the kind that Kafka evokes in The Castle. Fogle yearns to be like his father, but Lane Dean is shown regretting his decision to assume the responsibilities of fatherhood and adulthood too soon.

All of this suggests, once again, that Wallace had not yet imagined his way to a satisfying treatment of the themes that he wanted to address in The Pale King. Above all, he had not resolved the tension at the heart of the project: the problem of how to write an interesting book about boredom. This becomes especially clear in the last major episode in the book, when Meredith Rand describes her experience of mental illness to a fellow auditor, Shane Drinion. Drinion is a perfect IRS employee because he is, evidently, an Asperger’s type, devoid of social instincts but capable of intense, narrow focus. In one of the brief “Notes and Asides” at the end of the volume, Wallace describes Drinion as “happy”:

It turns out that bliss—a second-by-second joy + gratitude at the gift of being alive, conscious—lies on the other side of crushing, crushing boredom. Pay close attention to the most tedious thing you can find (tax returns, televised golf) and, in waves, a boredom like you’ve never known will wash over you and just about kill you. Ride these out, and it’s like stepping from black and white into color. Like water after days in the desert. Constant bliss in every atom.

The way Wallace tries to dramatize this bliss is by having Drinion, at the moment of total focus, literally levitate: while listening to Meredith Rand’s story, he starts to rise out of his chair. But this is “interesting” in exactly the style of Infinite Jest, with its unyielding liveliness and cartoon mobility—that is, it is interesting in the way The Pale King distrusts. His posthumous book shows that when Wallace died he was in the middle of the ordeal of purging and remaking his style. This is the kind of challenge that only the best writers set themselves. One of the many things to mourn about Wallace’s death is that we will never get to know the writer he was striving to become.

Adam Kirsch is a senior editor at The New Republic. This article originally ran in the August 18, 2011, issue of the magazine.