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His research in pornography over the years was still on his mind. Wallace’s original conceit for the novel may have involved not just tedium but pleasure. He made notes for a plot in which a group of rich businessmen run a video porn operation. They go into business with Drinion, an IRS immersive so talented that he sometimes floats above his seat while he works. Drinion had helped seize the business on behalf of the service for unpaid taxes. He comes now to double as their male lead in the movies. His great virtue is that he is so pale that he can be digitally erased and the porn viewer can have his own image replace it.15 It was the “Infinite Jest” videocartridge one iteration further along: what could be more addictive than watching yourself act out an addiction?16

The Bidart poem neatly connected to Wallace’s core interest in the IRS: how does it change a person’s internal life to work at something as dull as monitoring tax returns? The agents’ jobs were tedious, but dullness, in Wallace’s conceit, was what ultimately set them free. The lack of stimulation gave them a chance to open themselves up to experience in the largest sense of the word. The idea connected to Buddhism — Eastern religious practices had been a growing interest of Wallace’s for many years. (He liked to practice sitting meditation, he wrote Rich C., with “weird cultish Sikh and Buddhist groups, most of whom are very crazy in a very attractive way.”) The goal of the discipline was crucial to him — the inability to slow down his whirring mind was part of what he felt made his life so hard. As a character notes in the story “Good Old Neon,” which Wallace wrote around 2000, “What goes on inside is just too fast and huge and all interconnected for words to do more than barely sketch the outlines of at most one tiny little part of it at any given instant.” In the process of writing the novel he came to call The Pale King,17 he laid out its central tenet in one of his notebooks:

Bliss — a-second-by-second joy and 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. Instant bliss in every atom.

Wallace had explored this state briefly in Infinite Jest, partly through Lyle, the levitating guru in the weight room, and partly through John “No Relation” Wayne, the top player at the tennis academy, whose skill comes not from Wallace- or Hal-like cunning but from “frustrating mindless repetitive practice and patience and hanging in there.”18 With the help of researchers, Wallace assembled hundreds of pages of research on boredom, trying to understand it at an almost neurological level. He pulled down his Oxford English Dictionary and was intrigued to find that “bore” appeared in English in 1766, two years before “interesting” came to mean “absorbing.”

Wallace had four offices to write his novel in: his black room at home, a university office (rarely visited), a room put aside for him in Francis B.’s mother’s house, and a rented space in town.19 He was usually flummoxed by his lack of progress. DeLillo, to whom he wrote in worry, reassured him that a novel was “a long march to the mountains.” He took a second yearlong leave in 2000 and spent the first half of it trying to work and seeing a lot of movies. (Movies, he liked to say, were an addict’s recreation of choice.) Then he wrote letters about the movies. DeLillo was his chosen correspondent and his opinions were anti-elitist and mildly contrarian. For instance, he saw and loved the cyberthriller The Matrix—“visually raw and kinetic and riveting in a way that only something like Bochco’s Hill Street Blues was in ’81,” he wrote his friend — and hated the acclaimed Magnolia, which he found pretentious and hollow, “100 % gradschoolish in a bad way.” That summer he went to a retreat run by the Lannan Foundation in Marfa, Texas. There Wallace spent a pleasant month. He borrowed a nearby rancher’s two golden retriever puppies to walk and turned the books by the retreat’s alumni to the wall. This was his moment to approach the novel head-on, but the writing didn’t go particularly well, at least in retrospect. To Franzen, on his return, he wrote, “Almost everything I did there will have to be thrown away, but that, too, is good, in a way.” To Rich C., he was more downbeat: “I’m scared I can’t do good work anymore.”

Wallace was ever more in demand for his nonfiction. In the fall of 1999, Rolling Stone asked him if he wanted to write about a candidate in the upcoming presidential elections and he chose John McCain, the independent-minded Republican who was opposing George W. Bush for the presidential nomination. Wallace was politically fairly conservative; he’d voted for Ronald Reagan and supported Ross Perot in 1992, telling his friend Corey Washington, “You need someone really insane to fix the economy.” He came to combine midwestern conventionality with girlfriend-pleasing campus liberalism. In 2000 he voted for Bill Bradley in the Illinois primary. In truth politics did not generally matter much to him. He did not think who won an election could change what was broken. But in McCain Wallace saw another chance to explore the hollowing out of the American character. McCain’s campaign, which prided itself on openness and truthfulness, raised two intriguingly recursive questions in his mind. Was McCain genuinely honest or just portraying himself as genuine? If the former, were Americans so steeped in the complex double-talk of advertising they could not see genuineness when it appeared? And if the latter, were they so used to being tricked that it was now its own source of pleasure?

Wallace spent a week on the campaign trail in early February 2000 and, as was his style, ignored the top-level operatives to focus on the techies and hacks in the bus that followed McCain’s bus, the Straight Talk Express, dubbed (probably by Wallace) the Bullshit 1. He exaggerated on the way to make his point. He painted the major newspaper reporters — he called them “the twelve monkeys”—as haughtier and more alike one another than they even were and pretended the McCain campaign strategist was so afraid of him he would duck around the corner to avoid encounters (in fact they got along well; the gesture was playful, as the campaign strategist told a reporter for Salon in 2010.) And did two separate reporters really mistake Wallace for a bellboy and tell him to carry their suitcases? It seemed unlikely, but all this falsity contributed to creating a portrait of Wallace as an outsider, someone who could convey a truth readers weren’t getting elsewhere, real straight talk. In the end, what Wallace wanted to capture was what

the brief weird excitement [that the campaign] generated might reveal about how millennial politics and all its packaging and marketing and strategy and media and spin and general sepsis actually makes us US voters feel, inside.