Four Brain-Bending Doorstoppers that Will Challenge, Intrigue, and Possibly Break You

If you’re like me, you spent some variable period of time in your youth thinking you were smart, perhaps even some sort of unrecognized genius. And then you had an encounter with true genius—or the yawning abyss of your own dumbness—and had to issue a retraction. A retraction no one saw, because no one was taking your claims of genius seriously anyway. Perhaps, like me, your brush with true genius came in the form of a book, but not just any book. One of those thick, heavy tomes with a thousand pages of dense, twisty prose that left you humbled, scratching your head, and not entirely sure you “got” it. If you didn’t encounter one of those books, this is your chance: here are four huge books that will hurt your brain—but in a good way.
Night Film, by Marisha Pessl
Night Film is an imperfect book, but what it gets right it gets right. The spooky, creepy story of a legendary reclusive filmmaker who may or may not be involved with black magic and/or literally committing terrible crimes for verisimilitude in his films and the disgraced journalist who investigates the death of the filmmaker’s daughter, Night Film pulls off a head-spinning trick by establishing a very real-feeling universe that it then begins to destabilize, until you’re not sure what’s real and what’s not. Using a few modern multimedia tricks like reproducing webpages and articles right there on the page, that link out to extra information and images or videos on the web, the whole book slowly warps into an unreliable narrator that still somehow feels grounded in reality. The ending, on the surface, feels surprisingly reasonable—for a moment. Then you realize you don’t actually know if you can trust the words you just read. It’s one of those maddening narratives where you’re certain all the necessary information is right there in the pages, but you can’t seem to solve the puzzle.
House of Leaves, by Mark Z. Danielewski
When it comes to books that have the power to break brains, it begins and ends with House of Leaves. Part haunted house story, part celebration of the unreliable narrator, part brain-destroying puzzle you will never solve, this book is so crammed full of puzzles, wordplay, and downright trickery that endless Internet debates have sprung up around a single word choice. Everything about this book, from the layout on the page to the footnotes that circle back and lead you on a mazelike trip through pages you’ve already read, to the anagrams and mini-riddles that pepper every paragraph, gives the impression that the story itself is just the proverbial iceberg tip—and the roots go down into a deep, dark, place you might regret traveling to. In fact, the debate about what’s real, what’s imagined, and who, exactly, is telling the story in the first place continues to be lively and unlikely to be solved any time soon.
Infinite Jest, by David Foster Wallace
If you’ve never read Infinite Jest, it’s likely the only thing you know about it is that it’s incredibly long and concerns, to some extent, tennis. While both of these things are true, the book is complex, filled with a huge cast of characters who dip in and out of the narrative, and constructs what is essentially an alternate universe to our own that nevertheless feels absolutely real. While not as formally perverse as House of Leaves, Infinite Jest is a book that has several layers, and on first read you can only hope to understand the surface story, about an “Entertainment” that is so entertaining people starve to death watching it over and over; a tennis prodigy who loses the ability to express himself; and a future where time is subsidized, resulting in things like the Year of Glad, where “Glad” refers to the brand of trash bags. The rest of it is buried in the dense prose, clever plotting, and yards of complex and well-researched footnotes.
Haunted, by Chuck Palahniuk
Even if you haven’t read Haunted, you may have heard about one of the stories it contains: “Guts,” which is so disturbing in its imagery people reportedly walked out of several readings Palahniuk gave before the book published. The story of a writer’s retreat that takes a left turn into horror, there are two tracks to the book: One the tale of the trapped writers, who are locked inside an ancient theater with food and water and other comforts and told they cannot leave until three months have passed—time in which to write their masterpieces—and the other the short stories each writer produces while at the retreat. To say things go sour would imply you’re unfamiliar with Palahniuk’s work, but understanding how it all ties together is something else entirely. In fact, considering that the characters in the book are all obviously self-sabotaging, the best question you can ask after reading this book is simple: Why is it titled Haunted?
What’s the most mind-bending book you’ve ever read?