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Most Challenging Books You've Read

Other challenging books that I have liked are -
Catch-22
A Clockwork Orange
A Portrait of the Artist as a Young Man
Lolita (challenging for the content)
I find most romantic poetry a struggle, even if I enjoy some of it, too much goes over my head.

Other challenging books that I have like..."
Catch-22 and Lolita are still on my to-read list, but poetry in general doesn't come easy for me. It takes a while for it to click in my mind. I would read, ponder it unsuccessfully, go do something else, and then hours later I would exclaim out loud: "So that's what he or she meant!".
It was quite the challenge in school since we had to memorise verses upon verses of Arabic and French poetry.
Don Quixote. There it is. On the shelf. I think it's more the idea of giving up three months to it than anything else. Plus my copy is at least 15 years old, and I'd sneeze for the first two months of the read.


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Thanks Leslie!

I am sure that some of the philosophy books I read in college should be included but I don't retain a clear enough memory to say more than Heidegger and Kant were difficult.
And as much as I love her books, Dorothy Dunnett can be quite challenging to read (especially the first time through!). I would say The Game of Kings is particularly challenging due to quotations in Latin & French & a lot of vocabulary that is unfamiliar or just plain difficult.
Oh, and how could I forget to include One Hundred Years of Solitude? I had no idea of what was going on for most of that book!
It was hands down a three way tie between:
Paradise Lost by John Milton (due to tangled syntax),
Sartor Resartus by Thomas Carlyle (due to drunken logic),
a book of excerpts from major philosophical works by such authors as Kant, Georg Wilhelm Friedrich Hegel, and Søren Kierkegaard (due to all the complex terminology I had to learn to understand it and the complicated logic)
I really liked all 3 of these books despite the difficulty!
Books that I considered unnecessarily difficult (had no payoff aesthetically or learning-wise) I just abandoned; so those don't count.
Paradise Lost by John Milton (due to tangled syntax),
Sartor Resartus by Thomas Carlyle (due to drunken logic),
a book of excerpts from major philosophical works by such authors as Kant, Georg Wilhelm Friedrich Hegel, and Søren Kierkegaard (due to all the complex terminology I had to learn to understand it and the complicated logic)
I really liked all 3 of these books despite the difficulty!
Books that I considered unnecessarily difficult (had no payoff aesthetically or learning-wise) I just abandoned; so those don't count.

Gravity's Rainbow is a book I'll never finish . I started it at least five times and never could get beyond around 100 pages . I've given it up for good !
LauraT wrote: "Not being able to see the list - I'll do it tomorrow - I can easily say Ulysses for sure!"
Oh stupid me, I wasn't even looking at the list! Some weird choices. I don't agree about some of them.
For me personally I didn't find Cloud Atlas extremely difficult - not a light read for sure but I wouldn't consider it in the ranks of the most difficult books. And The Canterbury Tales in Middle English isn't so tough with the side notes and footnotes contained in the average copy. I found Chaucer fairly clear. And Ayn Rand was more boring than difficult for me.
But I definitely agree with the list maker about Nightwood by Djuna Barnes - extremely tough going! And I agree with him about absolom, absolom! as well - that one had to be read slowly with all the uncommon vocabulary, vast numbers of modifying clauses and super-long sentences! I suppose I agree with him about Woolf as well - definitely not light reading - but I would've probably chose The Waves as her most difficult to follow, not To the Lighthouse.
Oh stupid me, I wasn't even looking at the list! Some weird choices. I don't agree about some of them.
For me personally I didn't find Cloud Atlas extremely difficult - not a light read for sure but I wouldn't consider it in the ranks of the most difficult books. And The Canterbury Tales in Middle English isn't so tough with the side notes and footnotes contained in the average copy. I found Chaucer fairly clear. And Ayn Rand was more boring than difficult for me.
But I definitely agree with the list maker about Nightwood by Djuna Barnes - extremely tough going! And I agree with him about absolom, absolom! as well - that one had to be read slowly with all the uncommon vocabulary, vast numbers of modifying clauses and super-long sentences! I suppose I agree with him about Woolf as well - definitely not light reading - but I would've probably chose The Waves as her most difficult to follow, not To the Lighthouse.

Oh, I didn't even look at the list! From the Buzzfeed list I have read:
The Sound and the Fury by Faulkner (loved it despite the challenging stream-of-consciousness writing)
The Canterbury Tales - I've only read excerpts. I do find it difficult at times to deal with the old English spelling!
One Hundred Years of Solitude - lol, I thought of this one on my own! All those characters who had the same name was utterly confusing to me.
Gravity's Rainbow - maybe it is the science geek in me but I loved it! So much so I went right out and read V....
Being and Time by Martin Heidegger -- I don't think we read this in my college course; I think we read Basic Writings: Ten Key Essays, plus the Introduction to Being and Time but I still remember him as one of the philosophers that was almost impossible to understand!
Moby-Dick; or, The Whale -- This wasn't challenging. People might find sections of it boring or the book too long but the writing in itself was not hard.
The Silmarillion -- I LOVE the The Hobbit and The Lord of the Rings trilogy but despite several attempts at different points in my life, I just could not get interested in this.
Ulysses - enough said. I also read it with others but still wouldn't classify it as a "good reading experience". For me, the big plus is being able to check it off on so many lists!
The Castle by Franz Kafka -- honestly, I think I have read this but am not sure!
Absalom, Absalom! -- another Faulkner that I love!
The Name of the Rose -- I don't remember this as being particularly difficult but Eco does write using a lot of references to historical & cultural things, so that can be challenging if you aren't familiar with them. But I thought Foucault's Pendulum was more difficult than this...
Cloud Atlas - Some of the sections were more challenging than others but overall not so hard.
To the Lighthouse - to me this was more boring than challenging...
And there were 3 books on the list that I plan to read in 2016 (maybe I will change my mind about that now!) in addition to rereading the Faulkners:
The Corrections
Underworld
The Magic Mountain

Definitely challenging books in general. The list is just there to see wether you agree with it or not.
But speaking of the list, I ran across The Sound and the Fury in a bookshop which I somehow wandered into. And of course I ended up buying it.


Finnegans Wake was another; seriously, a book about River Iffey?
The Name of the Rose - Theology isn't really
A) Interesting to me, when it concerns different monks orders
B)easy to follow
Also, I just can't be bothered to check up the exact translation for every latin phrase there is, so I'm going with what I can translate, or as we would say in Italy "a spanne".
Otherwise the story is REALLY engaging and the characters are very well drawn.
It just doesn't make a good bedtime read, and right now that's all I've time for, but it means that I'm pretty tired and my brain is mush.
A) Interesting to me, when it concerns different monks orders
B)easy to follow
Also, I just can't be bothered to check up the exact translation for every latin phrase there is, so I'm going with what I can translate, or as we would say in Italy "a spanne".
Otherwise the story is REALLY engaging and the characters are very well drawn.
It just doesn't make a good bedtime read, and right now that's all I've time for, but it means that I'm pretty tired and my brain is mush.


Any poetry. I cannot figure out for the life of me the "hidden meaning", and when teachers tell you your idea of what the author is saying is wrong, it turned me off poetry. How does anyone know what the poet is saying for SURE unless the poet said "in this poem I was trying to say ...".

I also found Sea of Poppies challenging, I was so lost spending so much time reading lengthy footnotes that explained the references in the story, plus flipping to the glossary several times on every page to get the English word or phrase for the foreign words and phrases used in the text. With all those distractions I couldn't even say what the story was about!
I also struggled through Sophie's World, over my head.

Glad to know I am not alone. I think it is a shame as I would like to know more "elvish lore" but as you say, there are too many other books!
Gill, definitely challenging books in general but the list makes a good starting point (plus I love lists:P).

I also found Sea of Poppies challenging, I was so lost spending so much time reading lengthy footnotes tha..."
Funnily enough Evelyn, Sophie's World happens to be one the few philosophy books that didn't make me feel like a total idiot.
But it does seem like philosophy books are generally harder to read than other types, doesn't it?
Read 11 out of the 25. I don't agree, as Greg was saying, with defining them challenging for the most part.
Here's a list of what I've read and what I think:
1. The Sound and the Fury by William Faulkner – Loved it! Utterly, totally, absolutely!
2. One Hundred Years of Solitude by Gabriel García Márquez - Why challenging? Loved it as well
3. Infinite Jest by David Foster Wallace – more boring than challenging!
4. Moby-Dick; or, The Whale by Herman Melville – a masterpiece; long, sometimes a bit boring, but not at all difficult
5. The Corrections by Jonathan Franzen – loved it
6. The Magic Mountain by Thomas Mann – As above!
7. Ulysses by James Joyce This one has really been a challenge to me!!!
8. Underworld by Don DeLillo – didn’t liked it at all!
9. The Name of the Rose by Umberto Eco – This I don’t understand why it can be considered challenging. An easy read in my opinion – but liked it a lot. I was 15 when I read it!!!!
10. Cloud Atlas by David Mitchell – Like De Lillo’s
11. To the Lighthouse by Virginia Woolf - yes challenging; complicated enough!
Here's a list of what I've read and what I think:
1. The Sound and the Fury by William Faulkner – Loved it! Utterly, totally, absolutely!
2. One Hundred Years of Solitude by Gabriel García Márquez - Why challenging? Loved it as well
3. Infinite Jest by David Foster Wallace – more boring than challenging!
4. Moby-Dick; or, The Whale by Herman Melville – a masterpiece; long, sometimes a bit boring, but not at all difficult
5. The Corrections by Jonathan Franzen – loved it
6. The Magic Mountain by Thomas Mann – As above!
7. Ulysses by James Joyce This one has really been a challenge to me!!!
8. Underworld by Don DeLillo – didn’t liked it at all!
9. The Name of the Rose by Umberto Eco – This I don’t understand why it can be considered challenging. An easy read in my opinion – but liked it a lot. I was 15 when I read it!!!!
10. Cloud Atlas by David Mitchell – Like De Lillo’s
11. To the Lighthouse by Virginia Woolf - yes challenging; complicated enough!


Ulysses was a difficult first read for me but I ended up loving it. I read it with a very good group and am not sure whether I would have made it through on my own. I'm grateful for that group because this is now one of my favorite books and continues to grow on me. Looking forward to a reread in 2016 with everyone here.
Infinite Jest was brilliant. It's a commitment to get through but it's not difficult, I think.
There are quite a few on the list that I mean to get around to reading one day.


That makes two of us! Another difficult philosophy book is Al-Ghazali: Deliverance from Error & The Beginning of Guidance, it's old Arab philosophy, and it's not easy to get through.
Charbel wrote: "I considered getting Atlas Shrugged by Ayn Rand, which is on the list, but I settled instead for The Fountainhead. I hope it's something that I can sink my teeth..."
Curious to see what you think Charbel. I don't find Rand difficult at all, certainly nothing experimental like Woolf or Joyce. In general, I find Rand frustratingly simplistic and often boring, but that's just my personal reaction.
Curious to see what you think Charbel. I don't find Rand difficult at all, certainly nothing experimental like Woolf or Joyce. In general, I find Rand frustratingly simplistic and often boring, but that's just my personal reaction.


I look forward to you thoughts on this one, Charbel.

Nowadays, I've learned to trust my own thoughts about a poem. As I hope you do, one day.
Charbel wrote: "I'm curious about it as well Greg. I've heard so many things about Rand, ranging from "revolutionary" to "overrated". I remember someone telling me that she builds these stories with great morals b..."
I actually find that description fairly accurate Charbel.
I don't understand why some people find her "revolutionary" - if you end up feeling that way, maybe you can clear it up for me :)
I actually find that description fairly accurate Charbel.
I don't understand why some people find her "revolutionary" - if you end up feeling that way, maybe you can clear it up for me :)

I also agree Charbel, I have only read Atlas Shrugged, had to find out who John Galt was : ) well by the end when John Galt made his sixty page long speech which basically summarized the 1000 page long book, I wished I had never heard of him!

@Pink, I'm surprised that you found Les Misérables challenging! This is one of my all-time favorites. The version that I read was a translation by Norman Denny. I liked the way he picked out the two most boring chapters (the one about the convent system and the one about the War of Waterloo) and put them at the back as appendices, so as to keep the flow of the story uninterrupted.
I didn't find To the Lighthouse too hard to read, once I got used to Woolf's writing style in the beginning chapters.
I found Blaise Pascal's Pensées rather boring!
B the BookAddict wrote: "@Myst I think poetry is over-analysed. I think most teachers are teaching to a strict formula, guided by the curriculum about what students need to understand in each class. Who knows what a po..."
I think it matters what poems mean, and I think they do mean something fairly specific in some cases (they're not just a Rorschach blot) .. but I completely agree that the teaching of poetry is approached very badly! The first step is to enjoy them! Poems are often playful! Some poems are more difficult than others. Many are straightforward, narrative, and fun. Classes should begin with those and only gradually work up to the headscratchers! You don't take a person and throw them on the marathon starting line without any practice! But teachers do that with poetry.
Also, stressing people out trying to squeeze out every meaning is probably not the best way to begin. Of course the same thing often happens with literature in general. The focus of the teaching is on all the subtle meanings and suggestions .. great stuff, sure, but it needs to be worked up to.
For instance, my nephew Dylan just entered 9th grade, and his first assignment on the Odyssey was to find examples of "dramatic irony", "situational irony", "verbal itony", etc. How about a little focus on the story and why it's powerful, how it makes him feel first? What about a little idea of what life was like back then and what Homer was writing about? Why not start by capturing his imagination instead of bogging down right away in all sorts of dry literary distinctions?
I understand there's limited class time and lots of teaching standards items to tick off the list, but that way of doing things often fosters a life long hatred of literature where it should do the opposite!
I think it matters what poems mean, and I think they do mean something fairly specific in some cases (they're not just a Rorschach blot) .. but I completely agree that the teaching of poetry is approached very badly! The first step is to enjoy them! Poems are often playful! Some poems are more difficult than others. Many are straightforward, narrative, and fun. Classes should begin with those and only gradually work up to the headscratchers! You don't take a person and throw them on the marathon starting line without any practice! But teachers do that with poetry.
Also, stressing people out trying to squeeze out every meaning is probably not the best way to begin. Of course the same thing often happens with literature in general. The focus of the teaching is on all the subtle meanings and suggestions .. great stuff, sure, but it needs to be worked up to.
For instance, my nephew Dylan just entered 9th grade, and his first assignment on the Odyssey was to find examples of "dramatic irony", "situational irony", "verbal itony", etc. How about a little focus on the story and why it's powerful, how it makes him feel first? What about a little idea of what life was like back then and what Homer was writing about? Why not start by capturing his imagination instead of bogging down right away in all sorts of dry literary distinctions?
I understand there's limited class time and lots of teaching standards items to tick off the list, but that way of doing things often fosters a life long hatred of literature where it should do the opposite!

Perhaps it is considered revolutionary related to the period when she wrote it? I have it too in my to-read list but don't know when I will pick it up.
I can't remember challenging books. Though some were long or difficult, if I finished them it means that I liked them so I can't consider them challenging.
Recalled one! The Old Man and the Sea. It was a real torture to finish this book though it's pretty short. Another! The Martian. Oh my, this was another torture. It was a real challenge to finish it.
From the list I haven't read a lot of books because there are listed mainly books I already know I won't like like The Name of the Rose, Infinte Jest, James Joyce, Thomas Pynchon.
I've read The Sound and the Fury and hated it from the bottom of my heart. I will never ever read again a book by Faulkner.
Loved One Hundred Years of Solitude! Though I had to make a family tree to understand who was who.
Yes, perhaps The Castle by Kafka was a bit challenging. I have a love/hate relationship with Kafka: I hate how his books make me feel but I must admit that it's because of this that I consider him a genius. I feel the emotions of anguish he wants to convey to the reader.
Cloud Atlas wasn't challenging. I didn't like it but it wasn't a difficult or challenging read.
To the Lighthouse was very boring and tough and I also don't like stream of conciousness. So, yes, perhaps I can consider it a challenge to have finished it.

Well said, Bette & Greg!

I had a language arts class in the 8th grade where for 1 book report, we had a group assignment and the books weren't all "classic" literature. I had really been hoping to get The Phantom of the Opera, but I ended up getting Dragonsinger which turned me onto the Pern books. I did read Phantom about 5-7 years later and enjoyed it. I forget what the other book selections were, but I was happy to get 1 enjoyable book instead of all the normal assigned reading books.
(Please keep Lord of the Flies, The Outsiders, To Kill a Mockingbird, away from me. I appreciate they had a purpose to be in the curriculum, but that doesn't mean I had to enjoy them.)

I'm liking everyone's lists of books...I'll be keeping away from some of these, or at least bearing in mind they might take the extra effort!
dely wrote: "I can't remember challenging books. Though some were long or difficult, if I finished them it means that I liked them so I can't consider them challenging.
Recalled one! The Old Man and the Sea. It was a real torture to finish this book though it's pretty short. ..."
But that was only boring to death!!!!
Recalled one! The Old Man and the Sea. It was a real torture to finish this book though it's pretty short. ..."
But that was only boring to death!!!!
LauraT wrote: "dely wrote: "I can't remember challenging books. Though some were long or difficult, if I finished them it means that I liked them so I can't consider them challenging.
Recalled one! The Old Man an..."
I found it gripping - got through it in only a couple days, but I'm more the exception I think. :)
Recalled one! The Old Man an..."
I found it gripping - got through it in only a couple days, but I'm more the exception I think. :)
LauraT wrote: "Why Greg? It is considered a masterpiece. It's only I don't like Hemingway style in general!"
A lot of people do seem to find it boring, though I certainly didn't! :)
A lot of people do seem to find it boring, though I certainly didn't! :)
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I was looking at BuzzFeed's "25 Most Challenging Books You'll Ever Read" (which you can find here), and it got me thinking about the most difficult books that I've read.
I guess Ulysses tops the list, along with The Problems of Philosophy by Bertrand Russell for me. Also Confessions by Augustine of Hippo was a tough cookie.
What are some of the more challenging books you've read?
Note: By "challenging", I mean difficult to understand or follow. I don't mean whether you enjoyed it or not, of course do tell us whether you did enjoy it or not.