Ever picked up a book that was tough to get through? Maybe it was super long, really complex, or just hit you hard emotionally. I’m curious to hear about the most challenging books you’ve ever read and why they were so tough for you.
For me, it was ‘War and Peace’ by Leo Tolstoy. It’s not just the size, although it’s certainly a long read, but also the vast number of characters and the depth of the historical and philosophical discussions that made it a challenge. It took me a while to keep track of everyone and fully grasp the themes Tolstoy was exploring.
by MadMaxine666
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The Iliad and the Odyssey was a tough go as a kid and later as an adult, it was the Epic of Gilgamesh and The Canterbury Tales in its original language.
The Sound and the Fury. It was part of a college course and I found Faulkner’s style to be challenging.
To the Lighthouse nu Virginia Woolf.
I thought it was beautiful but reading the stream of consciousness was also very challenging. Haven’t read any of her other work yet
In the name of the rose
As someone else has said the silmarillion, though I have to admit that I’m bad at remembering names in general and that left me very confused at certain points.
Another one was the neuromancer, where I was stupidly trying to make perfect sense of things from the very beginning.
It took me 4 months to read *War and Peace* when I was 15… so I’ll go with that.
But as an adult it would have to be *The Pale King* by David Foster Wallace which I read about seven years’ ago. I have two degrees in literature and that man still makes no sense whatsoever.
I had trouble with *Don Quixote* because I like the kind of adventure books the author, Miguel de Cervantes, reflectively parodied. I identify too much with Don Quixote and I take it personally when Cervantes makes fun of him.
In Search of Lost Time. I started reading it about a year ago… And I’m still reading it. 🥲
Midnight’s Children
I had no cultural experience to draw from and had to keep looking everything up.
The five-part Book Of The New Sun series by Gene Wolfe. It’s one of my favourite ever reads, a top 10 book. But it is incredibly complex and needs to be read more than once to be fully understood. It’s an outright masterpiece.
Heart of Darkness.
Gödel, Escher, Bach
Worth it.
Probably Infinite Jest, but that was certainly the point. That took me a year to get through.
Gravityʼs Rainbow by Thomas Pynchon. I found it so wordy, so weird, and so hard to follow that I gave up after 200 pages.
House of Leaves. You need mirrors and shit.
Finnegans Wake by Joyce. Naked Lunch by William S. Burroughs.
Finnegan’s Wake – been off and on with it for years.
Finnegans Wake. Been climbing that mountain for 20 years now. The problem is that the longer you spend reading straight through the more sense it makes as your brain starts to slip into gear, but who had that kind of time? So then I have to go back to remember what was being described.
Blood Meridian – Cormac McCarthy
Heart of Darkness. I read it for literature studies and foolishly thought I could get through it in an afternoon because it was under 200 pages, but it was so so so dense to the point where I’d have to put it down and do something else every ten or so pages. It took me literal days! It’s undeniably well written and is an interesting critique of capitalist imperialism in the early 20th century ( and the mythology and bible references gave me tons to write my paper on!) but damn did I struggle getting through it!
Anything by Kant.
Moby Dick.
Infinite Jest.No structure , don’t understand who’s talking to whom.
For me it was Ana Karenina by Tolstoi – but in a good way. The reason for that is that it really got deep into each character and made me think a lot about them and myself.
Also Dune (the first book). There were some strong philosophical sentences where I just had to take a moment to take a deep breath and think about it. It’s definitely worth a reread.
Ulysses. Can’t say read cuz I can’t seem to read it
Foucaults discipline and punish, had a year long grad course centered on it and it was by far the most challenging text I’ve ever attempted
It took a long time for me to get the cadence of Blood Meridian, a deliberately bleak and opaque book.
Umberto Eco’s books, The Name of the rose and Foucault’s pendulum. Very dense writing and theories but I enjoyed the effort.
A Little Life by Hanya Yanagihara. I dropped it at 14% and don’t have the heart to pick it up until now but I want to finish it though but not now haha.
The first quarter of Wuthering Heights made me feel dumber than any other book. Admittedly I listened to an audiobook with a heavily accented narrator, but still the characters and plot didn’t click for far too long.
Brothers Karamazov. Can’t say I ever fully understood the significance of the story and never connected with the characters.
Ulysses by James Joyce.
I love a challenging book, but good grief, there were times I had to put this one down and contemplate whether it was worth continuing because it felt like I was just reading words on the page with nothing going in my brain. Talk about a struggle.
Blood Meridian. It’s so well written but so violent and the judge is so scary I had tears in my eyes. Took me about 6 weeks to finish because I couldn’t read it if I wasn’t in the right headspace
Milton’s Paradise Lost. English is not my mother tongue and reading poetry isn’t exactly easy either. Besides that, it’s centuries old, making the language even harder to grasp. I did make it, tho. Very proud.
I’ve definitely struggled my way through War and Peace like OP but I am glad I was reading it when I had access to the internet, lots of character charts to help keep everybody straight. (A little more difficult to find ones without spoilers).
My answer would likely be Brothers Karamazov. Definitely worth reading, but these brothers discussing their differing philosophical stances in a cultural context far removed from my own was really difficult.
If we are talking about emotionally challenging, then I would likely say Lolita. The beauty of the prose and the ugliness of H.H. make for a sickening juxtaposition (Nabokov is definitely a genius though)
Catch-22, at least at the beginning. After I realized I was supposed to be confused, I let the book take over and it ended up being one of my all time favorites.
The Hitchhiker’s Guide to the Galaxy… I read all five books in English when I’m a French-speaker. My reading comprehension in English is quite good but damn those were hard
Foucalts Pendulum by Umberto Eco. It gets better about 3/4 of the way through but man, the amount of words I had to look up and sentences I had to reread really put me off.
I’m usually pretty good at multitasking but two books that basically demanded I drop everything else and given them my full attention are House of Leaves and Malazan.
House of Leaves, for anyone who knows what it is, is kind of self-explanatory. There’s no way you can half-attention your way through that book.
Malazan less so but Malazan is so dense and unforgiving if you don’t pay attention I have to give it my full attention to follow it.
Recently The Indifferent Stars Above by Daniel Brown.
What the Donner Party went through was so horrific, at parts it was hard to read especially the children’s reaction to the cannibalism. Recommend it to any history lovers, but it was a tough read.
1q84. Love that book!
“The Third Policeman” by Flann O’Brien. “It was written in 1939 and 1940, but after it initially failed to find a publisher, the author withdrew the manuscript from circulation and claimed he had lost it. The book remained unpublished at the time of his death in 1966.” It was published posthumously, in 1967. It’s a wild ride and definitely NOT about a bicycle.
For some reason Dune…I’m going to give it another go soon, but I tried reading it about two years ago. I think I just need to learn how to pronounce the names and places. Maybe I wasn’t mentally in the mood to read that type of book, but I just remember having to DNF it.