David Foster Wallace

Based on Wikipedia: David Foster Wallace

In September 2008, one of the most gifted writers of his generation arranged a manuscript on his desk, wrote a note to his wife, and ended his life. He was forty-six years old. The novel he left behind, unfinished, would become a Pulitzer Prize finalist. The essays he'd written over two decades would continue to shape how we think about sincerity, entertainment, and what it means to pay attention in an age of distraction.

David Foster Wallace wanted to make you feel less alone.

That might sound like a strange mission statement for a writer known for thousand-page novels with hundreds of endnotes, sentences that sprawl across entire pages, and vocabulary that sends readers scrambling for dictionaries. But Wallace believed that beneath all the pyrotechnics, that's what fiction was actually for. "Fiction's about what it is to be a fucking human being," he once said. He wanted to write stories that were "morally passionate, passionately moral"—work that could reach through the page and remind you that someone else understood.

The Tennis Player Who Became a Writer

Wallace grew up in central Illinois, in the college town of Champaign-Urbana. His father taught philosophy at the University of Illinois. His mother taught English at the local community college and was eventually named Professor of the Year. It was, by most accounts, a household where ideas mattered.

But young David wasn't just a bookish kid. He was a regionally ranked junior tennis player, good enough to compete seriously. He later wrote about this period in an essay called "Derivative Sport in Tornado Alley," describing how he'd learned to use the peculiar wind patterns of the Midwest to his advantage—how growing up on those flat courts, with their unpredictable gusts, had taught him to calculate angles and trajectories that baffled opponents from calmer regions.

Tennis would remain a lifelong obsession. Years later, he'd write some of the most celebrated sports journalism ever published, including a piece about Roger Federer for The New York Times that transcended the genre entirely, becoming a meditation on beauty, physical genius, and what it feels like to watch someone operate at the absolute limit of human capability.

At Amherst College, Wallace double-majored in English and philosophy. He wrote two senior theses—one in each department. The philosophy thesis, on modal logic and free will, was good enough to be published posthumously as a book. But it was the English thesis that would launch his career.

That thesis became his first novel, The Broom of the System, published in 1987 when Wallace was just twenty-four. Critics immediately compared him to Thomas Pynchon and John Irving. The New York Times called it "a manic, human, flawed extravaganza." A major talent had arrived.

The Problem with Irony

To understand what Wallace was trying to do with his writing, you need to understand what he was reacting against.

By the late 1980s, American fiction had been dominated for decades by what's loosely called postmodernism—a style characterized by irony, self-reference, and a knowing wink at the reader. Postmodern novels often broke the fourth wall, commented on their own artificiality, and treated sincerity as naive. The implicit message was that we're all too sophisticated to believe in anything earnestly.

Wallace saw this as a trap.

In a 1990 essay called "E Unibus Pluram: Television and U.S. Fiction," he argued that irony had become "an agent of a great despair and stasis in U.S. culture." The problem wasn't that irony was ineffective—it was too effective. Television had absorbed irony so completely that hip detachment had become the default mode of American consciousness. Commercials mocked their own products. Sitcoms winked at their own conventions. Everyone was in on the joke.

But here's the thing about irony: it's purely negative. It can tear down, but it can't build up. It can show you what's false, but it can't show you what's true. And after thirty years of relentless ironic deconstruction, Wallace believed American culture had lost the ability to talk about what actually matters—love, meaning, purpose, how to live—without immediately undercutting itself.

"The next real literary 'rebels' in this country," he predicted, "might well emerge as some weird bunch of anti-rebels... who have the childish gall actually to endorse and instantiate single-entendre principles."

In other words: the radical act would be sincerity.

Infinite Jest

Wallace's second novel took five years to write and arrived in 1996 as a 1,079-page behemoth with 388 endnotes, some of which contained their own footnotes. Infinite Jest was set in a near-future North America where the years are sponsored by corporations (the Year of the Depend Adult Undergarment, the Year of the Whopper), and the plot involves a tennis academy, a halfway house for recovering addicts, Quebecois separatist terrorists, and a film so entertaining that anyone who watches it loses all will to do anything else.

That last element—the lethally entertaining film, also called "Infinite Jest"—is the novel's central metaphor. Wallace was obsessed with entertainment and addiction, with the American pursuit of pleasure and the emptiness that pursuit so often produces. The novel asks: What happens to a culture that optimizes entirely for feeling good? What happens when we get exactly what we want?

The book's structure mirrors its themes. The endnotes force you to constantly flip back and forth, disrupting the passive consumption that Wallace saw as entertainment's danger. You can't just sink into Infinite Jest the way you sink into a Netflix binge. It demands your active participation.

Time magazine would later name it one of the hundred best English-language novels published between 1923 and 2005. But at the time, reactions were mixed. Some critics found it brilliant; others found it exhausting, self-indulgent, or simply too much. Wallace himself seemed ambivalent about its reception. He'd wanted to write something that would make readers feel less alone, but he worried that the book's difficulty might have the opposite effect.

This Is Water

In 2005, Wallace delivered a commencement address at Kenyon College that would become, after his death, the text for which he's probably most widely known.

He began with a parable: Two young fish are swimming along when they pass an older fish who nods and says, "Morning, boys. How's the water?" The two young fish swim on, and eventually one looks at the other and asks, "What the hell is water?"

Wallace's point was that the most obvious, ubiquitous realities are often the hardest to see. We swim through our lives surrounded by assumptions and automatic responses that we never examine because they're just... there. The water.

The speech—later published as a small book called This Is Water—is Wallace at his most direct. No postmodern games, no endnotes, no hundred-word sentences. Just a writer trying to tell a group of young people something true about how to live.

The really important kind of freedom involves attention, and awareness, and discipline, and effort, and being able truly to care about other people and to sacrifice for them, over and over, in myriad petty little unsexy ways, every day.

This wasn't abstract philosophy. Wallace was describing a daily practice—the conscious choice, moment by moment, to resist the default settings of self-centeredness and frustration. In the supermarket checkout line, when you're tired and the person ahead of you is slow, you can choose how to interpret the situation. You can assume they're an inconsiderate idiot, or you can imagine that maybe they're having the worst day of their life, maybe they just got terrible news, maybe they're dealing with something you can't see.

Neither interpretation is necessarily more accurate. But one leads to misery and the other leads to something like grace.

The only thing that's capital-T True is that you get to decide how you're going to try to see it. You get to consciously decide what has meaning and what doesn't.

The Essay as Art Form

While Wallace's novels got the most attention, some of his finest work appeared in magazines. He wrote about cruise ships for Harper's Magazine, producing an essay so funny and perceptive that it became the title piece of his first nonfiction collection, A Supposedly Fun Thing I'll Never Do Again. He covered John McCain's 2000 presidential campaign for Rolling Stone, somehow turning political journalism into a meditation on what leadership might mean in an age of total cynicism.

He wrote about the porn industry, state fairs, conservative talk radio, and a Maine lobster festival. For each assignment, he brought the same relentless curiosity and the same willingness to examine his own reactions. A Wallace essay didn't just report on its subject—it reported on the experience of encountering that subject, complete with all the writer's doubts, digressions, and second-guesses.

The lobster piece, "Consider the Lobster," was commissioned by Gourmet magazine as a straightforward food article. Wallace delivered something else entirely: a philosophical inquiry into animal suffering, the ethics of boiling creatures alive, and whether it's possible to enjoy a food festival while genuinely considering the experience of the food. Gourmet, to their credit, published it anyway.

Some critics have questioned the accuracy of Wallace's nonfiction. Jonathan Franzen, who was one of Wallace's closest friends, has said he believes Wallace invented dialogue and incidents—that "those things didn't actually happen." The characters in his essays do tend to speak in suspiciously perfect, crystalline sentences. Whether this makes them less valuable depends on whether you think nonfiction should be strictly factual or whether it can be something more like testimony—a record of how one particular consciousness processed the world.

The Darkness

Wallace struggled with severe depression for more than twenty years. He was hospitalized multiple times. He dealt with alcoholism and drug addiction. In 1989, he spent four weeks at McLean Hospital in Massachusetts—the same psychiatric institute where Sylvia Plath and Robert Lowell had been treated—completing a detoxification program. He later said the experience changed his life.

For most of his career, an antidepressant called Nardil (the generic name is phenelzine) kept his depression manageable. It was an older medication, a monoamine oxidase inhibitor, which required him to avoid certain foods and had various side effects. But it worked. On Nardil, Wallace could write. He could teach. He could function.

In June 2007, Wallace got sick—severe stomach pains that his doctors attributed to an interaction between his medication and something he'd eaten at a restaurant. They recommended he stop taking Nardil. He agreed, partly because he'd begun to worry the drug might be interfering with his writing.

This was a catastrophic mistake.

The depression returned with devastating force. Wallace tried other medications. He tried electroconvulsive therapy. Eventually, he went back on phenelzine, but it no longer worked the way it had before. Sometimes, with psychiatric medications, you can't go back. The chemistry has changed.

On September 12, 2008, Wallace hanged himself at his home in Claremont, California. He left behind a wife, a half-finished novel, and a body of work that continues to shape American literature.

The Unfinished Novel

The Pale King was published in 2011, three years after Wallace's death. His editor, Michael Pietsch, assembled it from the pages and notes Wallace had left behind—a necessarily incomplete and speculative reconstruction of what the finished book might have been.

The novel is about boredom.

Specifically, it's about the IRS (the Internal Revenue Service, the American tax collection agency) and the people who work there processing tax returns. Wallace had become fascinated with the idea that boredom might be a kind of key—that the ability to pay attention to boring things, to concentrate without stimulation, might be the most important and least valued skill in modern life.

This was connected to everything else he'd written about. The lethal entertainment of Infinite Jest. The attention and discipline of This Is Water. The seductions of irony. Wallace seemed to believe that what ailed American culture was fundamentally an attention problem—that we'd become so desperate for stimulation that we could no longer tolerate the ordinary moments that make up most of existence.

The Pale King didn't reach as wide an audience as his other works. It's fragmentary by nature, and the subject matter is intentionally anti-dramatic. But critics generally praised it, and it was nominated for the Pulitzer Prize.

What Remains

Wallace's influence extends far beyond the literary world. This Is Water has become a kind of secular scripture, quoted at graduations and shared on social media. His concerns about irony, entertainment, and attention seem more relevant with each passing year. When he wrote about the dangers of optimizing for pleasure, smartphones hadn't been invented. When he worried about distraction and the erosion of interiority, Twitter didn't exist.

He saw something coming. Or rather, he saw something that had already arrived but that most people hadn't yet recognized.

Wallace also left behind a more complicated legacy. After his death, his former girlfriend Mary Karr came forward with allegations of abuse—that he'd thrown furniture at her, physically forced her out of a car, followed her son home from school, and attempted to buy a gun to kill her ex-husband. Other women, including former students, reportedly contacted her to share their own experiences. These accounts are impossible to reconcile with the compassionate, self-aware voice of his writing. They're also impossible to ignore.

How do we hold these things together? The writer who wanted to help people feel less alone and the man who allegedly terrorized the women in his life? The celebrant of attention and the person who couldn't control his own impulses? There's no tidy answer. Wallace himself wrote obsessively about the gap between our public performances and our private realities, about the hideous things that can coexist with genuine decency inside a single consciousness.

Perhaps the best we can do is take what's valuable from his work while refusing to look away from the full picture. He was right about a lot of things. He was also, by multiple accounts, capable of terrible cruelty. Both things are true.

The Water

Wallace once said that the hardest thing about writing fiction was figuring out "how to put yourself in the service of something greater than your own ambitions." He wanted his work to matter in the way that great literature has always mattered—not as entertainment, not as demonstration of cleverness, but as a genuine attempt to help people live.

Whether he succeeded depends on who you ask. But his central insight—that attention is a moral and spiritual practice, that the stories we tell ourselves about reality shape the reality we experience, that the opposite of addiction might be connection—has proven remarkably durable.

We are still swimming in the water he tried to describe. The irony, the entertainment, the self-regard, the endless distraction. If anything, the currents have grown stronger. But occasionally someone reads his work and decides to pay attention differently, to resist the default settings, to remember that the people around them have inner lives as complex and vivid as their own.

That's what he wanted. That's what he was trying to do.

He couldn't save himself. But maybe, for some readers, he left behind something that helps.