Some books are more difficult to read than others. In some cases, this is because the book is poorly written. However, other books are intentionally written to be difficult to read.

Perhaps this is because they want to be more exclusive with their readership. Or maybe the author just wanted to mess with the audience. Either way, many of those books have worked their way into literary history for one reason or another.

• Finnegan's Wake by James Joyce: James Joyce wrote several complicated books. But this is no doubt the most difficult to read. It could be argued that Finnegan’s Wake is his masterpiece and one of the most brilliant pieces of English literature. It could just as easily be argued that it’s complete gibberish.
• Infinite Jest by David Foster Wallace: David Foster Wallace only published two novels before he committed suicide in 2008. But Infinite Jest remains a monument of literature to this day. Its title is both an homage to Hamlet and an inside joke at the book’s staggering length (close to 1,100 pages).
• Atlas Shrugged by Ayn Rand: Who is John Galt? That’s the question that drives people to read this mammoth book by Russian novelist, Ayn Rand. It’s either that, or sadomasochism. Because it’s both lengthy of page and dense of text.
• Moby Dick by Herman Melville: Everyone knows the tale of Captain Ahab and the white whale. But not many people have actually read it themselves. Perhaps reading Moby Dick has become a white whale of sorts for some people. Perhaps they can go read it in a Starbucks coffee shop, named after a character in the book. #FunFact
• House of Leaves by Mark Z. Danielewski: Full of footnotes, different fonts, and oddly laid out page designs, House of Leaves is the literary equivalent to taking LSD. It’s a book-within-a-book-within-a-book. Yet as complicated as it is, it’s also fascinating to behold.
• The Trial by Franz Kafka: There’s a reason that Franz Kafka got a word (Kafkaesque) named after him. Because he set the standard for super weird literature. The Metamorphosis, in which a guy turns into a bug, is relatively easy to understand compared to The Trial. It’s longer, more complicated, and fewer people read it as a result.
• The Silmarillion by J.R.R. Tolkien: The ultimate fantasy dork’s fantasy. The Silmarillion is the history of the world and characters in The Lord of the Rings series. It’s the book version of the making-of DVD’s that went with the movies. Only this has more elvish names.
• The Brothers Karamazov by Fyodor Dostoyevsky: There’s just something about Russian literature. It’s so cold and boring outside in Russia—so all they do all day is sit inside, drink vodka and write long novels. Not to mention, everyone’s names sound similar. The Brothers Karamazov is probably the most confusing, but anything by Dostoyevsky or Tolstoy could have honestly made this list.
• Anything by William Faulkner: The Sound and the Fury. As I Lay Dying. Absolom! Absolom! Take your pick. They’re all complicated and crazy. Faulkner loves to write in stream of consciousness, use unreliable narrators, and crank the southern gothic up to an 11. Not that he’s not a talented writer, but he makes you work to appreciate his work.
• If On a Winter’s Night a Traveler by Italo Calvino: This is a book about the book you’re reading. You are the main character of the book. Except the chapters are out of order and you spend the entire book trying to find and read the rest of the book. It’s very postmodern.
• The Bible: There are an estimated two billion Christians in the world. Only about 10% or so have actually read the entire Bible. That’s not surprising considering how long and complicated it is. Written by dozens of authors over hundreds of years and available in over 2,000 different translations.

https://www.youtube.com/watch?v=laXcJyx9xCc