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12 Challenging Books Readers Struggle to Finish

They may be worth reading, but it will take you ages.

As a former English major, I've had the misfortune pleasure of coming across some of the most intellectually challenging literary works. Believe me, I love to read and I enjoy challenging myself but when it's Friday night a week from finals and you're assigned to read Paradise Lost, no one should fault you for turning to SparkNotes. It just so happens that a lot of literary titles that are put on the pedestal of the best literature in history happen to be complicated AF (though very much worth reading). Yes, no one can deny that Moby-Dick is an American classic, but if you're telling me you've never once yawned or snoozed when you read it, I don't quite know if I can trust you.

 

From puzzling allusions (including religious references easily missed by people unfamiliar with religious texts) to drawn out plots to overly complicated language, here are 12 literary works that readers have struggled with finishing (let alone understanding). 

 

1. The Canterbury Tales | Geoffrey Chaucer

The Canterbury Tales are a collection of the funniest, most complex, and most awarding tales. Chaucer's use of Middle English language, however, make them hard AF to understand. 

 

2. Moby-Dick | Herman Mellville

 

Through the plot of Moby Dick is pretty forward, the actual story, comprised of overly-described prose and complex biblical and mythological references set in a slow pace of it can be particularly hard to grasp. By the last page, you may not understand what just happened. 

 

3. King Henry IV | Shakespeare 

While Shakespeare's witty works comprised of Early Modern English have proven to be difficult for many bookworms to get through, King Henry IV is particularly challenging. There is a lot going on, schemes from left and right, and (in my opinion) it's not quite exciting enough to be a page turner. Titus Andronicus, on the other hand, is definitely filled with a ton of shocking action to carry you to the finish line.

 

4. Paradise Lost | John Milton

This epic poem is naturally long enough to keep you reading for weeks, but throw in Milton's obscure language, endless biblical references, and run-on sentences and you may give up half way in.

 

5. Infinite Jest | David Foster Wallace 

With a whopping 1, 079 pages, Infinite Jest is among the longest novels ever written. Known for its unconventional narrative style, this experimental book is filled with complex ideas and language, immense detail, and endless footnotes which will keep you busy for awhile.

 

6. War and Peace | Leo Tolstoy

War and Peace is brilliant. It's also really long. Period.

 

7. Atlas Shrugged | Ayn Rand

Atlas Shrugged can be eye-opening, but its philosophical and political ideas presented in lengthy monologues can be tough to grasp. The novel use of elements from multiple genres - mystery, romance, and sci-fi - may further confuse readers.

 

8. Ulysses | James Joyce

The most experienced, intellectual, and seasoned reader can come to a crossroads when they pick up this book. It's widely known as one of the most difficult novels due to Joyce's layered allusions, stream-of-consciousness technique, and rich vocabulary.  Ironically enough, those same qualities have made it one of the most revered book in history, and many readers who have managed to finish it have argued that the struggle is worth it.

 

9. Finnegans Wake | James Joyce

Like Ulysses, Joyce's experimental attitude reflects on the pages of Finnegans Wake. Written over the course of seventeen years, it experiments with the English language, incorporates stream-of-consiouness technique, and has a lack of structure that can take readers just as long to finish as the author did writing it. 

 

10. Gravity's Rainbow | Thomas Pynchon

Named by Time Magazine as one of the all-time American novels, Gravity's Rainbow has managed to dazzle and complex readers since 1923. Its 700-plus pages introduces readers to over 400 characters amidst a backdrop of World War 2 action giving readers a lot to deal with before they reach the last page.

 

11. The Brothers Karamazov | Fyodor Dostoyevsky

If you've noticed a theme on this list, it appears that many readers often struggle with literary works containing religious and/or philosophical ideas. The Brothers Karamazov has both. The novel deals with complex ideas, such as right vs wrong, human conscience, moral responsibility and other religious matters written over the course of 700-plus pages, enough the challenge many readers.

 

12. The Bible

One of the most widely read books, The Bible contains a series of complex stories written in intricate language whose meanings have lead to various interpretations and debate around the world. Given that stories from the Bible were originally passed along orally, its no wonder that that it can be more challenging for people to read it on paper versus hearing it aloud.

 

 

Let us know if you've managed to finish any of these titles and which you'd highly recommend to your fellow readers!

 

Featured image shows illustration from The Canterbury Tales via Three Gold Bees