10 Most Difficult Books To Read (And Why You Should Give Them a Try)

Ever been halfway through a book and wondered if your brain had just quit on you?

We’ve all been there, frantically flipping back pages, trying to figure out where the plot went or if we missed a crucial detail.

Well, if you think that’s bad, let me introduce you to a whole new level of literary brain-benders—books that are famously hard to read.

You know, the type of books that make you question your life choices, ask yourself why you’re reading them in the first place, and yet, when you finally close that last page, you feel like you’ve accomplished something massive.

Think of it as climbing Mount Everest but for your mind.

In this guide, we will walk through some of the most notoriously difficult books ever written, what makes them tough, why they’re worth the struggle, and how to tackle them without losing your sanity.

So, if you’re ready to flex your literary muscles, let’s look into some of the hardest books you’ll ever read.

1. Finnegans Wake by James Joyce

Let’s start with the heavyweight champion of confusing books—James Joyce’s Finnegans Wake.

If you’ve ever opened it, you might have thought it was written in a different language.

You’re not wrong—Joyce mixes English with other languages, strange wordplay, and what seems like nonsense.

But there’s more going on here than meets the eye.

Why It’s So Hard:

• Joyce took 17 years to write this book, and you can tell. It’s packed with stream-of-consciousness writing, puns, and wordplay that blends multiple languages.
• The book begins mid-sentence and ends mid-sentence, which sounds confusing, but it’s a reflection of the novel’s circular theme. In a nutshell, Joyce was playing around with the idea that history and time are cyclical (thanks to philosopher Giambattista Vico’s ideas).
• There’s no linear plot to follow. It’s like you’re dropped into a dream (literally), with characters, events, and settings all shifting like clouds in the sky.

Why It’s Worth It: If you go into it expecting a straightforward story, you’re in for a world of confusion. The best advice for Finnegans Wake?

Don’t try to understand every word—just feel it. Joyce himself said you should enjoy the rhythm and sound of the language.

Think of it like an abstract painting. You might not “get” every stroke, but you can still appreciate the whole thing.

The themes here—transformation, rebirth, and the complexity of the human mind—are deep.

Plus, you get some pretty intense wordplay that’s often hilarious if you’re up for deciphering it.

2. Infinite Jest by David Foster Wallace

David Foster Wallace’s Infinite Jest is a huge book—over 1,000 pages—and it’s not just long, it’s complicated.

Packed with footnotes, some of which even have footnotes of their own, this novel can make your head spin.

It’s set in a not-too-distant future where entertainment, addiction, and society’s problems collide in a massive, confusing mess.

Why It’s So Hard:

• The story jumps between different characters and timelines. Wallace doesn’t make it easy to follow along, and you’ll find yourself flipping back and forth a lot.
• The footnotes contain important details, so skipping them isn’t an option. Some readers even recommend having two bookmarks—one for the main story and one for the footnotes!
• It’s a non-linear book, which means the events don’t happen in a clear order, and you’ll need to piece things together as you read.

Why It’s Worth It: Despite its complexity, Infinite Jest is funny, deep, and a mind-bending exploration of addiction, entertainment, and the way society distracts itself from existential despair.

It’s not just a book about tennis or rehab—it’s a massive, chaotic reflection of modern life.

You might feel lost for a good chunk of the book, but when the pieces start coming together, it’s like a literary lightbulb moment.

Is it worth reading? Absolutely. Just don’t expect to breeze through it. Think of it more like a puzzle that’s worth the time it takes to solve.

3. Being and Time by Martin Heidegger

If you’re up for some serious philosophy, then Heidegger’s Being and Time is one of the most influential, but also one of the hardest, books you’ll ever read.

It’s about the nature of existence—what it means to “be”—and it digs deep into questions about life, time, and death.

Why It’s So Hard:

• Heidegger uses new words that he either makes up or redefines, so you’ll often need to look up what he’s talking about.
• The ideas are very abstract. It’s not a casual read—it’s heavy, dense, and requires a lot of thinking.
• You’ll probably need to read each paragraph more than once to understand it, and even then, it might not make sense until you finish the whole book.

Why It’s Worth It: If you can make it through the dense prose and new vocabulary, Being and Time offers a profound meditation on life, death, and what it means to live authentically.

Heidegger basically says that we’re all “thrown” into the world with no predetermined purpose, and how we deal with that uncertainty shapes our lives.

Sure, it’s not an easy ride, but the philosophical insights are immense.

It’s one of those books that stays with you long after you’ve finished it, as you find yourself thinking about its themes in your everyday life.

P.S. If you’re also interested in life-changing reads, you can check 10 Must-Read Spiritual Books That Can Change Your Life. These books offer powerful insights and inspiration for personal growth and transformation.

4. Gravity’s Rainbow by Thomas Pynchon

Thomas Pynchon’s Gravity’s Rainbow is often called one of the most complex books ever written.

Set during World War II, it is so fragmented and full of strange digressions that following it is like trying to solve a puzzle without knowing what the picture is supposed to look like.

Why It’s So Hard:

• The plot is non-linear, fragmented, and full of digressions. It’s set during World War II, focusing on the mysterious V-2 rocket and the paranoia surrounding it. But there are so many characters and storylines that it’s easy to lose track of what’s happening.
• Pynchon’s style is postmodern, which means he’s constantly playing with time, reality, and narrative structure. One moment, you’re reading a highly detailed historical description, and the next, you’re thrown into a bizarre, almost surreal situation that seems to have no connection to the plot.
• It’s packed with obscure references. Seriously. You’ll probably want to keep Google nearby because Pynchon drops references to everything from science and history to mythology and pop culture. It’s like reading a novel and a textbook at the same time.

Why It’s Worth It: Despite its difficulty, Gravity’s Rainbow is an incredibly rewarding read if you can stick with it.

At its core, it’s a novel about control—whether it’s political, technological, or psychological.

Pynchon explores themes like paranoia, entropy, and the decline of systems, all wrapped up in a darkly humorous, absurd narrative.

Yes, it’s challenging, but once you get into the rhythm, it’s an experience like no other.

You might not catch everything on the first read (or the second), but the more you invest, the more you get out of it.

5. The Sound and the Fury by William Faulkner

William Faulkner’s The Sound and the Fury is a Southern Gothic novel that explores the downfall of the Compson family.

But what makes it tough is the way the story is told—it’s not straightforward at all.

The first section is narrated by Benjy, a mentally disabled man whose perception of time is jumbled, making it hard to follow.

Why It’s So Hard:

• The novel is split into four sections, each told from a different perspective. The first section is narrated by Benjy, a mentally disabled character whose perception of time is completely disjointed. Faulkner uses stream-of-consciousness writing, so the narrative jumps around without warning.
• The second section is narrated by Quentin, whose mental state is deteriorating, adding another layer of complexity. The third part is told by Jason, who is bitter and detached, and the final section is from an omniscient perspective.
• It’s a book about time, memory, and the failures of the Southern aristocracy, but the way Faulkner plays with time can be confusing. You’ll need to piece the story together bit by bit as you move between narrators.

Why It’s Worth It: If you can get through the fractured narrative, The Sound and the Fury is a deeply emotional and powerful novel.

Faulkner’s writing is rich, and his exploration of family, loss, and the passage of time is profound.

It’s the kind of book that, when you finish it, you feel like you’ve truly earned the experience.

6. The Castle by Franz Kafka

Franz Kafka’s The Castle is a classic of existential literature, and it’s a book that captures feelings of confusion and frustration perfectly.

The story follows a man named K. who arrives in a village ruled by a mysterious Castle, but no matter how hard he tries, he can never gain access to it.

The story is unfinished, adding to its sense of hopelessness.

Why It’s So Hard:

• Kafka’s writing is filled with bureaucratic absurdity. K. spends the entire book trying to gain access to the Castle, but he’s constantly blocked by strange, nonsensical bureaucratic procedures. It’s like the literary version of being stuck in an endless line at the DMV.
• The characters and situations are intentionally frustrating. Nobody ever gives K. a straight answer, and everything seems to be shrouded in mystery. It’s meant to convey the feeling of alienation, frustration, and the absurdity of modern life.
• The novel is unfinished. It ends abruptly mid-sentence, leaving you hanging without closure—just like K.’s endless struggle to reach the Castle.

Why It’s Worth It: Despite the frustration (which is kind of the point), The Castle is a brilliant meditation on the absurdity of bureaucratic systems and how they dehumanize individuals.

Kafka’s writing is sharp, darkly humorous, and hauntingly prophetic about the way modern institutions operate.

You might not get closure at the end, but you’ll definitely walk away with a deeper understanding of Kafka’s bleak yet insightful view of society.

7. Absalom, Absalom! by William Faulkner

Another Faulkner novel, Absalom, Absalom! takes the difficulty of The Sound and the Fury to a whole new level.

This novel tells the story of Thomas Sutpen and his quest to build a dynasty in the American South, but it’s told in a way that’s fragmented and full of long, complex sentences.

Why It’s So Hard:

• Faulkner’s sentences go on for pages. Some paragraphs are so long and detailed that you might need to stop and catch your breath halfway through.
• The story is told through multiple narrators, each with their own interpretation of the events. You have to piece together the truth yourself as you move between different viewpoints.
• The novel uses stream-of-consciousness, which makes it hard to know what’s real and what’s just the thoughts of the characters.

Why It’s Worth It: Though it’s challenging, Absalom, Absalom! is a deep and powerful exploration of race, identity, and the legacy of slavery in the South.

Faulkner’s complex narrative structure mirrors the complexity of the history he’s exploring, and while it’s a difficult read, it’s also incredibly rewarding for those who stick with it.

8. Nightwood by Djuna Barnes

Nightwood by Djuna Barnes is a modernist novel that explores themes of gender, sexuality, and identity.

Set mostly in 1920s Paris, it’s a lyrical and fragmented story about the emotional struggles of a group of outcasts, but its unusual style makes it a tough read.

Why It’s So Hard:

• The writing is extremely lyrical and often blurs the line between internal thought and outward speech. Barnes uses a stream-of-consciousness style that can leave readers unsure of what’s happening in the plot.
• The novel’s themes of identity, desire, and sexual fluidity were radical for its time, and Barnes doesn’t make it easy to grasp. The characters are fractured, their relationships tangled, and the narrative is dense with emotion and symbolism.
• Dialogues in the novel are often abstract, jumping between ideas without much explanation, which makes for a challenging but intriguing read.

Why It’s Worth It: Nightwood is one of the earliest novels to explore LGBTQ+ themes openly, and Barnes’s portrayal of love and identity is raw, emotional, and ahead of its time.

Though it’s difficult, the book’s beauty lies in its language and its willingness to explore complex human emotions.

9. War and Peace by Leo Tolstoy

Leo Tolstoy’s War and Peace is one of the longest and most detailed books ever written, and it’s often considered a masterpiece of world literature.

Set during the Napoleonic Wars, it follows a huge cast of characters as they navigate life, love, and war in Russia.

Why It’s So Hard:

• It’s over 1,200 pages long, so just finishing it is a massive challenge.
• Tolstoy goes on long philosophical tangents about life, fate, and history, which can slow down the pace of the novel.
• There are lots of characters to keep track of, each with their own complex stories, so you’ll need to pay close attention to who’s who.

Why It’s Worth It: Despite its length, War and Peace is a brilliant exploration of life, love, and war, and it offers some of the most beautiful writing you’ll ever read.

The characters feel incredibly real, and Tolstoy’s insights into human nature are timeless.

It’s a challenge, but if you can get through it, you’ll have experienced one of the greatest books ever written.

10. The Divine Comedy: Inferno by Dante Alighieri

Dante Alighieri’s The Divine Comedy: Inferno (completed in the early 14th century) is an absolute classic—one of the most famous works of world literature.

But make no mistake, just because it’s well-known doesn’t mean it’s easy. Inferno has symbolism, theological references, and allegorical meaning that can leave you scratching your head.

Why It’s So Hard:

• The structure of Hell is detailed and full of symbolism. Each of the nine circles represents a different sin, with punishments that fit the nature of the sin committed.
• Dante mixes mythology, religion, and history, referencing figures from the Bible, ancient Rome, and Greek mythology. If you’re unfamiliar with these references, it can be hard to keep up.
• It’s written in terza rima, a three-line rhyme scheme, which makes it a poetic challenge on top of the deep philosophical and religious themes.

Why It’s Worth It: Though challenging, Inferno is a powerful story about sin, justice, and the human condition.

Dante’s journey through Hell is both a literal adventure and a metaphor for the soul’s journey toward redemption.

The poem’s vivid imagery and moral depth make it a rewarding read, especially for those interested in theology and philosophy.

Challenge Yourself with These Difficult Books

So, there you have it—ten of the most challenging books in literary history.

Each one of these works pushes the boundaries of storytelling, whether through complex narrative structures, deep philosophical themes, or experimental writing styles.

Are they hard to read? Absolutely. But they’re also incredibly rewarding.

These books offer more than just stories—they provide insight into human nature, society, and the way we interact with the world around us.

They challenge us to think, to reflect, and to engage with literature on a deeper level.

So, if you’re up for the challenge, grab a copy of one of these literary beasts, settle in, and prepare for an unforgettable reading experience.

It won’t be easy, but trust me, it’ll be worth it.