The Most Challenging Books in Literature

The most difficult book, Finnegans Wake, creates an incomprehensible loop, challenging even the smartest readers.

### The Ultimate Challenge: 5 Most Difficult Books to Read
* 📚 These five books are renowned for their complexity, including one that **creates its own language** and another that **keeps scholars occupied for centuries**.
* 📖 "Infinite Jest" features **388 endnotes within 200 pages**, intentionally disrupting linear reading and leaving readers feeling **distracted**, earning a **six out of ten** on the difficulty scale.
* 🚀 "Gravity's Rainbow," which was deemed **unreadable** by the Pulitzer Prize board, follows multiple characters during World War Two and is packed with **over 400 characters**, making it a **seven out of ten** on the difficulty scale.
* 🧠 "The Sound and the Fury" employs a **stream-of-consciousness style**, telling the same story from **four different perspectives**, and is filled with **time shifts and jumbled memories**, resulting in an **eight out of ten** on the difficulty scale.
* 🔍 "Ulysses" condenses the Odyssey into a **single day in Dublin**, filled with literary puzzles and symbols, showcasing Joyce's **extensive vocabulary with over 30,000 unique words**, making it a **challenging read**.
* 🌪 Finally, "Finnegans Wake" is considered the most difficult, described as an **incomprehensible loop** with a **ten out of ten difficulty rating**, leaving even critics **baffled by its complexity and structure**.
* ⏳ The intricate nature of these texts demands **immense dedication and patience**, with "Finnegans Wake" potentially taking **decades to fully grasp**.

These are the five most difficult books you will ever encounter, including a book that makes up its own entire language, a book intended to keep professors busy for centuries, and a book whose endnotes have endnotes. And only one of these hits a ten out of ten on the difficulty scale. There's a good chance you've heard of these books before, but what you probably don't know is why they're so difficult to read. Take, for instance, Infinite Jest. Upon first glance, it looks pretty normal, albeit a bit long, but if you take a look at this character map, then you start to see why this is so unreadable. Then if you flip to the back of the book, hundreds of pages of endnotes. 388 endnotes, in 200 pages. Now, David Foster Wallace did this on purpose to disrupt the linearity of the text, and your experience as a reader. He wanted you to feel distracted, flipping back and forth...as if

We don't have enough trouble focusing as it is. And if you're looking for a resolution, well, there is none. Actually, Wallace disagrees. He says the answers all exist, but just beyond the last page. We'll give it a six out of ten on the difficulty scale. But it's about to get a lot tougher. Because this next book was supposed to win the Pulitzer Prize in 1974. However, the board decided they would rather give the prize to nobody before they let Gravity's Rainbow win. There was no official statement as to why, but the board did say the book was unreadable, overwritten, obscene, and turgid, which is just another word for tediously pompous. And I can understand why, because it follows several characters who are trying to uncover the secrets of an enemy rocket during World War Two. And a large plot point is that one man's erections may predict missile

strikes. That's obviously an oversimplification because this novel has over 400 characters, and it covers quantum mechanics and speculative metaphysics and many other narrative threads. Benjamin McEvoy says the difficulty is all front-loaded. So if you get past the first hundred pages and get your bearings on what's going on, it becomes a much more enjoyable experience. So seven out of ten on the difficulty scale, zero out of ten on the do I want to read it scale. Okay. Stream-of-consciousness is a writing style that puts you inside of someone's head and gives you all of their random, fragmented thoughts. And you can't ever get out to actually see what is really going on. And these thoughts are unexplained because of course you're not going to be explaining your thoughts to anyone. It is your own inner dialog. Not only that, but you don't always think in complete sentences and there is no punctuation. Basically, it is extremely difficult

to follow. And if you read Sound and the Fury, you will actually see the same story four times from four different points of view, largely in the stream-of-consciousness style. The only problem is the first point of view is from a 33-year-old man who has the mind of a small child. Perhaps he has Down's syndrome or autism; they didn't really have those diagnoses back then. And the specifics aren't really that important. What is important is that you are stuck in his head for 30 years of memories. All jumbled up. Without Faulkner telling you that time has shifted. Sometimes he uses italics to indicate time shifts, but not always. And sometimes he slips back out of italics when he's still amidst a time shift, leading to mass confusion for the reader. So how do you end up telling the same story four times? You fail a lot. This is Faulkner's self-proclaimed

most splendid failure. He wanted to tell a story of a little girl named Caddy. And each section is an attempt to do that. But in each one, she eluded him. He says, I never could tell it right, though I tried hard and would like to try again, though I'd probably fail again. He took those four failures. He put them together and suddenly it was a success. Great success. We'll give it an eight out of ten. I got to say, before doing this video, I had never considered picking up this novel, and I really had no idea what it was even about. But I now know that Ulysses is a novel that turns the 20-year journey of the Odyssey into a single day in Dublin. And it's full of puzzles, which I love puzzles, but these are not the casual kind of puzzles that you do at home.

with your family. No, these are literary puzzles. For scholars. For example, there is a section on sirens that is set up like a musical score. So it has a prelude with jumbled up fragments that return later in the section. It has the jingle of Boylan's car interspersed and the tap of the piano tuner's cane, which creates an underlying rhythm. Joyce put so many puzzles in this book that he says ...it would keep professors busy for centuries, arguing over what I meant. And that's the only way of ensuring one's immortality. But the difficulty doesn't stop there. Ulysses is also extremely symbolical. It uses so many references that it will make your head spin. Popular songs of the time, folklore, Shakespeare, Dante, Aristotle, operas. And this was 1920. So it's not like your

Taylor Swift's knowledge is going to go very far. Each section is a completely different style. And most of it is stream of consciousness. And if you can say one thing about Joyce, it's that he had a God-like vocabulary. We're talking 30,000 unique words. That is more than the number of unique words in all of Shakespeare's work. Not only that, at the time, 337 of these words had never even been in print before. Bugger off, schlep, pornosophical. Not only does it have a ton of words, it also has different languages. James Joyce knew 17 languages. So there's Latin, French, entire paragraphs of Italian. I'm afraid even a dictionary is not going to help you with this one. But maybe the craziest thing about this book is the thunderwords. There are ten of these, and each one is 100 letters. Here's an example with Adam Harvey pronouncing it, because I cannot.

Lukkedoerendunandurraskewdylooshoofermoyportertooryzooysphalnabortansporthaokansakroidverjkapakkapuk. I mean, that's clearly unintelligible, but it's not! Actually, it is just variations of shut the door in a bunch of different languages. I think this might be a little over my head. And most of the general public avoids this one. Surprisingly, even most of the critics don't like this. The introduction reads, There is no agreement as to what Finnegans Wake is about, whether or not it is about anything or even whether it is, in any ordinary sense of the word, readable. H.G. Wells, someone I consider pretty smart, He wrote 50 books...He was so upset, He wrote Joyce a personal letter saying, Who the hell is this, Joyce Who demands so many waking hours of the few thousands

I have still to live. Vladimir Nabokov called it a cold pudding of a book. A persistent snore in the next room. Even his own brother rebuked him for writing an incomprehensible night-book. This book ends with the first half of the first sentence and begins with the last half of the last sentence. So it is the perfect loop, on repeat, forever. A book that never ends. Like an inescapable fever dream. And that is a solid ten out of ten on the difficulty scale. If anyone has even attempted this, you have my utmost respect. Let me know when you finish it in 20 years.

The 5 Most Difficult Books Ever! (Fiction)

Drawn to Books

These books are known for their extreme difficulty, with one creating its own language and another having endnotes with endnotes.

"Infinite Jest" disrupts linearity with 388 endnotes in 200 pages, aiming to distract the reader.

"Gravity's Rainbow" was deemed unreadable and pompous by the Pulitzer Prize board, with a complex plot involving characters uncovering enemy rocket secrets during World War II.

The Complexity of "The Sound and the Fury"

The novel "The Sound and the Fury" is challenging due to its over 400 characters and intricate narrative threads, covering topics like quantum mechanics and metaphysics.

The stream-of-consciousness writing style immerses readers in fragmented thoughts, making it difficult to follow the story.

Faulkner tells the same story four times from different perspectives, using time shifts and italics inconsistently, which adds to the confusion for the reader.

The Splendid Failure of Telling Caddy's Story

The author struggled to tell the story of a little girl named Caddy, experiencing multiple failures in each attempt.

However, by combining these failures, he ultimately achieved great success with the narrative.

The novel "Ulysses" is highlighted for its unique approach, turning the Odyssey's 20-year journey into a single day in Dublin, filled with complex literary puzzles and symbolic references.

James Joyce's work is characterized by a stream of consciousness style and an extraordinary vocabulary, with 30,000 unique words, surpassing Shakespeare.

He was fluent in 17 languages, incorporating Latin, French, and Italian into his writing.

Joyce's "Finnegans Wake" features ten "thunderwords," each 100 letters long, and has been met with confusion and criticism for its complexity and unintelligibility.

The book is criticized by Vladimir Nabokov and even the author's brother for its incomprehensibility.

It features a unique structure, ending with the first half of the first sentence and beginning with the last half of the last sentence, creating a perfect loop.

The challenging nature of the book is emphasized, with the author acknowledging the difficulty and offering respect to anyone who attempts to finish it.