You’ve probably seen the spine. It’s usually blue, thick as a brick, and looks vaguely threatening on a coffee table. Infinite Jest. It is the ultimate "literary bro" litmus test, the book people buy but rarely finish. Honestly, that’s a shame. Because the actual world of books by David Foster Wallace is way more than just a 1,000-page endurance test about tennis and addiction.
He was a writer who was terrified of being bored. Or rather, he was terrified of the things we do to avoid being bored.
If you’ve ever scrolled through TikTok for three hours and felt like your brain was turning into lukewarm soup, Wallace was talking to you before TikTok even existed. He saw the "Information Age" coming and tried to write a manual for how to stay human inside of it. It wasn't always pretty. Sometimes it was incredibly dense. But it was always, fundamentally, about trying to feel less alone.
The Big One: Infinite Jest and the Trap of Pleasure
Let’s get the elephant out of the room. Infinite Jest (1996) is the reason we’re still talking about him. It’s set in a future where years are named after corporate sponsors—like the Year of the Depend Adult Undergarment.
The plot? It’s a mess, but a brilliant one. There’s a film so entertaining that anyone who watches it loses the will to do anything else. They just sit there, staring at the screen, until they die. It’s a lethal joke. Meanwhile, you’ve got kids at an elite tennis academy grinding their bodies into dust and recovering addicts at a halfway house just trying to make it through the next five minutes without a hit.
The book is famous for its footnotes. There are 388 of them. Some are just a few words; others are multi-page essays on chemistry or fictional filmographies.
People think the footnotes are him being a show-off. Kinda, maybe. But they also force you to move. You have to physically flip back and forth. You can’t just passively consume the story. You have to work for it. That was his whole point: if you don't work for your life, someone else will sell you a version of it that makes you a zombie.
The "Easy" Entry Points (The Essays)
If you want to understand the hype without losing four months of your life, start with the non-fiction. Wallace was arguably a better essayist than a novelist.
In A Supposedly Fun Thing I’ll Never Do Again (1997), he goes on a luxury cruise and basically has a nervous breakdown because the "forced fun" is so depressing. He observes the way the staff tries to anticipate every need before you even have it. It sounds like paradise, right? Wallace argues it’s actually a kind of death. It turns you into a giant, screaming infant.
Then there’s Consider the Lobster (2005).
- The title essay is legendary.
- He goes to the Maine Lobster Festival for Gourmet magazine.
- He ends up asking: "Is it okay that we’re boiling these things alive just because they taste good?"
He doesn't give you a preachy answer. He just makes you sit with the discomfort. That was his specialty. He’d take something mundane—a state fair, a tennis match, a dictionary—and peel back the skin until you saw the weird, pulsing heart underneath.
The Short Stories: Brief Interviews and Darker Corners
If the essays are the "fun" Dave, the short stories are the "dark" Dave. Brief Interviews with Hideous Men (1999) is... well, it’s a lot. It’s a series of transcripts where men reveal the most manipulative, gross, and "hideous" parts of their psyches.
It’s not an easy read. It’s meant to make you squirm. He was obsessed with the way we use language to lie to ourselves. We say we’re being "honest" when we’re actually just trying to get what we want.
His first collection, Girl with Curious Hair (1989), is more of a young man’s book. It’s flashy. It’s got stories about Jeopardy! and Lyndon B. Johnson. It’s where he was testing his muscles. But even then, you can see he was worried about the same thing: how do we connect with people when everything in our culture is trying to turn us into irony-poisoned spectators?
The Pale King: The Unfinished Battle with Boredom
Wallace died by suicide in 2008. He left behind a literal pile of papers on his desk. This became The Pale King (2011).
It’s a book about the IRS.
Yes. Taxes.
The "hero" is a guy who can sit still and do mindless data entry for hours without losing his mind. Wallace believed that the next frontier of human bravery wasn't going to be war or space travel. It was going to be the ability to handle crushing, soul-sucking boredom without reaching for a distraction.
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The book is unfinished, so it feels like a ghost. Some chapters are perfectly polished; others are just notes. But there’s a section in there—the "Chris Fogle" chapter—that is maybe the best thing he ever wrote. It’s about a "wastoid" who stumbles into an accounting class and has a religious experience about the importance of paying attention.
Why You Should Actually Care in 2026
We live in the world Wallace was scared of. We are constantly stimulated, constantly marketed to, and constantly lonely.
His writing is a reminder that "paying attention" is a choice. You don't have to be a slave to your "default setting"—the voice in your head that says you’re the center of the universe and everyone else is just in your way.
If you’re looking to dive into books by David Foster Wallace, don't start with the biggest one just to say you did. Start with the essay about the cruise ship. Read the one about Roger Federer. See if his voice clicks with yours. It’s a voice that’s neurotically smart, occasionally annoying, but deeply, desperately sincere.
How to Start Reading Wallace Without Giving Up
Don't treat it like school. Treat it like a conversation with a really smart, really anxious friend.
- Pick up "A Supposedly Fun Thing I’ll Never Do Again." Read the title essay. If you don't laugh, he’s probably not for you.
- Watch the "This Is Water" commencement speech. It’s on YouTube. It’s the closest thing to a "thesis statement" for his entire life.
- Try "Infinite Jest" with a buddy. There are whole online groups (like Infinite Summer) dedicated to reading it in chunks. Doing it alone is how people end up using it as a doorstop.
- Skip the bits that bore you. Seriously. Even Wallace fans skim the heavy technical stuff sometimes. The goal is to get to the "human" parts.
The real magic of these books isn't the big words or the complex structures. It’s the moment you read a sentence and think, "Wait, I thought I was the only person who felt that way." That’s why he wrote. And that’s why, despite everything, people are still lugging those heavy blue books around.
The next step for you is simple. Grab a copy of his essay collection Consider the Lobster. Flip to the middle. Read the piece about the Illinois State Fair. It’s the perfect introduction to how he saw the world—half-absurd, half-beautiful, and completely worth noticing.