5 most difficult books to read

Okay, I have chewed on most of these. I liked Gravity's Rainbow, but I failed the first time I read it. Then I read Inherent Vice, which is probably Pynchon's most accessible book (and I recommend it). Then I took another bite and it worked for me.

Ulysses, I first read but didn't really comprehend. Then I found the Odyssey trick I posted above, and I read it again. I understood more. Not all, by any means, but more.

Finnegan's Wake? Forget about it. I started it, and I have read passages, but as a novel, or whatever the hell it is, no.

The Sound and Fury I read as a dare from a creative writing teacher. I survived, and appreciated the Shakespeare reference of the title. That is all.

I have tried to read Infinite Jest three times so far. I may try a fourth, or I may just give up.

Also would make my list for hardest to read:

Underworld, by Don DeLillo. Dense. Nonlinear. A lot of references to the 1930's I had no access to.
In Search of Lost Time, by Marcel Proust, as much on volume as anything. I pick it up every few years, and it is worth reading.
Nightwood, by Djuna Barnes. Dense. So fucking dense. Felt more like poetry that had been encased in concrete.
Atlas Shrugged, Ayn Rand. There are 70 pages spent on one speech. Or maybe I just hated it.
David Foster Wallace was a pretty good essay writer, even if he loved footnotes and sub-footnotes. The only one he overdid was the one on tennis. Infinite Jest, nearly a thousand pages? He had to have padded that one. He needed a good editor, I think.

The only Pynchon book I tried was V, I think. It abruptly changes to a new, unrelated scene in the middle of a page. William Burroughs did that on purpose with a few of his books. He'd cut the manuscript into pieces and put them back in a different order. Possibly they were still mostly chronological anyway, but you can easily see where the breaks are. His editor should have said, "Bill, what the hell are you doing?"
 
Gravity's Rainbow for me every time. Tried five times back in the day and never got close to finishing it.

I managed the The Atrocity Exhibition and The Naked Lunch but wish I hadn't.

Also ashamed to say I completed Atlas Shrugged but I did skip the 4,342 page Galt radio diatribe.

My five would probably be made up with the manual for my Kurzweil synthesiser. Utterly unfathomable.
I am a fan of Ballard's work, but I get why The Atrocity Exhibition would be an issue. They call it a novel, but it isn't. And it isn't a short story collection, or an omnibus. The main character keeps changing his name. Hell, it doesn't have a definable beginning or end. What it was is an attempt to deal with his wife's death and his instant single-fatherhood amid the violence of the late '60s as pushed through a New Wave lens. The New Wavers were always experimenting. I think Zelazny was the most successful of the group when it comes to writing an understandable story while playing with form and conventions, but most of Ballard's work is easier to access than The Atrocity Exhibition.
 
David Foster Wallace was a pretty good essay writer, even if he loved footnotes and sub-footnotes. The only one he overdid was the one on tennis. Infinite Jest, nearly a thousand pages? He had to have padded that one. He needed a good editor, I think.

The only Pynchon book I tried was V, I think. It abruptly changes to a new, unrelated scene in the middle of a page. William Burroughs did that on purpose with a few of his books. He'd cut the manuscript into pieces and put them back in a different order. Possibly they were still mostly chronological anyway, but you can easily see where the breaks are. His editor should have said, "Bill, what the hell are you doing?"
Inherent Vice is a good book if you want to try Pynchon. It is pretty linear, the story of a stoner PI in 1970s California, investigating a land deal. A comic-postmodern-noir-detective story, and it is pretty funny. There is bit of a Big Lebowski feel, but Doc has more agency than The Dude in the story, and the '70s setting works well. There was a movie adaptation that was supposed to be quite good, but I haven't caught it yet.
 
I've read bits of Ulysses and might try it sometime. I did enjoy Dubliners, which is similar wordplay and style but rooted much more closely to reality.

Loved Cryptonomicon (despite being confused by lots of the military stuff - at the time, I vaguely knew there had been some of WW2 in the Pacific and there was a place called Pearl Harbor - had never heard of any of the rest) and the Baroque Trilogy is among my favourite books ever. To be fair, I read half of book 2 while stuck in a US consulate waiting room for six hours, when I'd have read anything, but I'd already loved the first one.

Books I've never managed to finish, or ended up skimming faster and faster:
The Fountainhead - Ayn Rand. Its main virtue is being shorter than Atlas Shrugged.

One Hundred Years of Solitude - Gabriel Garcia Marquez. Something about magical realism and unreliable narrators and half the characters having the same name, and I never got more than 1/3 through it.

Island by Aldous Huxley - it's like Brave New World, only boring. Whereas The Doors of Perception is brilliant and manages to describe the experience of being on drugs and the desire to be so better than anyone else. (The Doors were named after it)

Dickens. You can tell he was generally paid by the word... I did finally read David Copperfield when Project Gutenberg got it. The first 200 pages are fun, the last 200 pages a scathing takedown of Victorian society in London, but god the 700 pages in between were bad! If you stop when he meets the drip that he's going to marry, and return once she's finally died of TB (signalled really obviously from the off), it improves it no end.

I've seen the 30-minute play version of Moby Dick, and a 15-minute version of War and Peace, which were both brilliant, so I don't really want to read them now!

Kafka's The Trial they don't know what order the chapters are meant to go in (he wanted all his manuscripts destroyed after death), but it's meant to be Kafkaesque (funny, that...) so while it makes it hard to follow, the plot goes in circles anyway.

Obviously there's books that are hard to read because they're total dross. Some are redeemed by comedy value: challenge someone to read 50 Shades or Anything of Gor without wincing, groaning or laughing. (Houseplant of Gor is a parody but even harder to read aloud with a straight face)
 
Dante's Inferno and Paradise Lost.

Read them the first time when I was around 12, it was a slog.

Had to(and I stress those words) read Tale of Two Cities in High School.

Aside from that I don't read anything I'm uninterested in, because I've never been interested in trying to sound trendy, artsy and oh, so super smart.
 
Marion Zimmer Bradley's, Mists of Avalon was a damn hard read for me. I always thought the editor should have been fired.
 
Inherent Vice is a good book if you want to try Pynchon. It is pretty linear, the story of a stoner PI in 1970s California, investigating a land deal. A comic-postmodern-noir-detective story, and it is pretty funny. There is bit of a Big Lebowski feel, but Doc has more agency than The Dude in the story, and the '70s setting works well. There was a movie adaptation that was supposed to be quite good, but I haven't caught it yet.
Okay, I'll give it a try. It also sounds a bit like Chinatown, although that is just a guess. It seems like more PI stories are set in Los Angeles than anywhere else.
 
Dante's Inferno and Paradise Lost.

Read them the first time when I was around 12, it was a slog.

Had to(and I stress those words) read Tale of Two Cities in High School.

Aside from that I don't read anything I'm uninterested in, because I've never been interested in trying to sound trendy, artsy and oh, so super smart.
There was a translation of The Inferno that I read years ago that was pretty good. Now I can't remember the person who did it. I thought his name was Michael Cardi, but I seem to be wrong.

Didn't Dickens often publish in serial form, so he wasn't that concerned with length?
 
I am a fan of Ballard's work, but I get why The Atrocity Exhibition would be an issue. They call it a novel, but it isn't. And it isn't a short story collection, or an omnibus. The main character keeps changing his name. Hell, it doesn't have a definable beginning or end. What it was is an attempt to deal with his wife's death and his instant single-fatherhood amid the violence of the late '60s as pushed through a New Wave lens. The New Wavers were always experimenting. I think Zelazny was the most successful of the group when it comes to writing an understandable story while playing with form and conventions, but most of Ballard's work is easier to access than The Atrocity Exhibition.
Ballard published his full autobiography in 2013 called Miracles of Life. It overlaps with the fictional Empire of the Sun, but there are major differences. The biggest one is that his parents were with him during his internment by the Japanese. Then it keeps going with his post-war return to Britain, where he had never been before. It sends with a trip to modern Shanghai where he was able to find the buildings used for the camp. By that time, Shanghai had sprawled so such that it enveloped the formerly rural setting.
 
Marion Zimmer Bradley's, Mists of Avalon was a damn hard read for me. I always thought the editor should have been fired.
I liked that book very much.

If you want to take a second bite at Ulysses, here is what I found. Find a good translation of Homer's The Odyssey.
Homer's "The Odyssey" was source material for my "Cascade Fire," I incorporated whatever was handy of its flow, plot points, characters, and a few tidy language quirks as I could. YMMV.

Cormac McCarthy, Blood Meridian: This story makes the story of Clint Eastwood's film Unforgiven look like Mary Poppins. It's that dark and that twisted. I generally like dark and twisted, but this story tested even me. It's a story of the American West on an acid trip. Dense and difficult, but one of my favorite books because he's such an amazing wordsmith. The Judge is one of the greatest, most memorable villains in the history of literature.
My friend Shane wrote a book about that book. Had a release party at the office. I bought a copy of Shane's, of course. I hope to read Cormac's someday, but recently was recommended to read another of his first.

You're welcome for the plug, Shane.

I know I like the other Cormac McCarthy very much.

The first book I started but didn't finish was Samuel Delaney's "Dhalgren". Some liked it very much. I thought it was interminable, but then I was still in high school, though it made enough of an impact that I sketched my interpretation of the "orchid" weapon he described despite not identifying as a visual artist.

As is the case for many of the other books I've seen mentioned here, I have no impulse to try (or re-try) it again. I do hope to finally read "Moby Dick" this year, though.
 
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Moby Dick has come up a number of times here. It was my favorite when I was just starting high school, and still ranks high with me. I'm disappointed in the idea that one has to 'slog' through the details of whaling; that is an integral part of the book to me. Consider the scene where Ishmael and Queequeg apply to ship aboard the Pequod. The two Quaker owners disagree - one doesn't want a heathen; the other tests Queequeg's ability with the harpoon. Queequeg gets the job. And that's crucial to the book - the question of who you are versus what you can do. Both streams are there, the practical, scientific, and ethnographic, and the moral and ethical. It is the two streams of the vision of America - a land where your worth is in what you can do rather than the color of your skin or the gods you worship. But that morality is undermined by blind obsession. The ship is the Pequod - all but one of the crew die in the pursuit of the white whale; the Connecticut Tribe is the Pequod - almost exterminated by the white whale of intolerant British colonizers.
 
Vladimir Nabokov's "Lolita" comes to mind, but for reasons that differs from most in the thread so far. It's a well-written book often considered one of the classics, making its way onto many top 100 books of all times list, but the book is incredibly uncomfortable to get through at times due to the more-than-questionable theme. Not only that, the narrator jumps from English to French CONSTANTLY. It's just a word or a phrase here and there, and sometimes it's possible to infer what he's trying to say from the context, but other times it's truly difficult to follow along if your French is rusty or non-existent like mine. These two things combined made it a true slog for me to get through. (It didn't help that I had to read for a school project rather than it being my own choice either.)
 
Vladimir Nabokov's "Lolita" comes to mind, but for reasons that differs from most in the thread so far. It's a well-written book often considered one of the classics, making its way onto many top 100 books of all times list, but the book is incredibly uncomfortable to get through at times due to the more-than-questionable theme. Not only that, the narrator jumps from English to French CONSTANTLY. It's just a word or a phrase here and there, and sometimes it's possible to infer what he's trying to say from the context, but other times it's truly difficult to follow along if your French is rusty or non-existent like mine. These two things combined made it a true slog for me to get through. (It didn't help that I had to read for a school project rather than it being my own choice either.)
Oh, I loved Lolita! Yeah, it is difficult, but it is so brilliant. It is the best, purest example of an unreliable narrator I have ever read. You can see places where some character's response is completely at odds with what Humbert says. The friction shows where Humbert is editing their responses and words to fit his narration. All the places where he explains that Lolita loved him and wanted to stay with him, where what she does and says are completely at odds with that. Character responses to his conversations. It is subtle, brilliant, and manifests in an utterly uncomfortable experience in his head, which should be uncomfortable.

Sorry, I just love how good that book is.
 
Oh, I loved Lolita! Yeah, it is difficult, but it is so brilliant. It is the best, purest example of an unreliable narrator I have ever read. You can see places where some character's response is completely at odds with what Humbert says. The friction shows where Humbert is editing their responses and words to fit his narration. All the places where he explains that Lolita loved him and wanted to stay with him, where what she does and says are completely at odds with that. Character responses to his conversations. It is subtle, brilliant, and manifests in an utterly uncomfortable experience in his head, which should be uncomfortable.

Sorry, I just love how good that book is.

I agree with you on many parts. It was this very book that made me want to write my first "unreliable narrator" story myself. It was also one of my first proper encounters with what I believe some people refer to as "Tragic comedy". And the story is certainly brilliant at times - but the keyword you mentioned for me was still uncomfortable, and that made it tricky. To this day, this book - despite being truly difficult for me to get through - was one of the more inspiring. Especially since Vladimir Nabokov was Russian and his masterful way of using other languages in such a natural and flawless way is impressive beyond belief. Made me feel that maybe I could also write something half-decent in English one day, despite it not being my native language.

Surprisingly, I had no issue with some of the other works mentioned in here. I loved Moby Dick, thoroughly enjoyed The Trial by Kafka, and got through The Sound and the Fury just fine. I think I struggled with "The Magus" by John Fowles more than all three of those books, and that's another classic I can warmly recommend.
 
I agree with you on many parts. It was this very book that made me want to write my first "unreliable narrator" story myself. It was also one of my first proper encounters with what I believe some people refer to as "Tragic comedy". And the story is certainly brilliant at times - but the keyword you mentioned for me was still uncomfortable, and that made it tricky. To this day, this book - despite being truly difficult for me to get through - was one of the more inspiring. Especially since Vladimir Nabokov was Russian and his masterful way of using other languages in such a natural and flawless way is impressive beyond belief. Made me feel that maybe I could also write something half-decent in English one day, despite it not being my native language.

Surprisingly, I had no issue with some of the other works mentioned in here. I loved Moby Dick, thoroughly enjoyed The Trial by Kafka, and got through The Sound and the Fury just fine. I think I struggled with "The Magus" by John Fowles more than all three of those books, and that's another classic I can warmly recommend.
I had less problems with The Trial than with The Metamorphosis.

Some people find The Name of the Rose, difficult. I absolutely loved it, even before I found a book that translated all the Latin passages. So much Latin.

Sanderson I find difficult, but that is a different discussion.
 
I've read Ulysses and didn't mind it. Moby Dick made my brain hurt and I could never finish it.

I have read War and Peace, although it took me three attempts over about two years. Don Quixote was another one that was something of an arduous labour. I quite enjoyed The Name Of The Rose.

I'm about to attempt Demons by Dostoevsky. Wish me luck...
 
I haven't tried the top 5 listed. I was able to read the first volume of Sandburg's Lincoln and had to give it up. Gore Vidal warned that it was excruciatingly boring. I loved Moby Dick, but I loved the details of whaling life as well as the language and plot. I waded through Thackery's The Luck of Barry Lyndon. I decided that books were expensive in those days, and people wanted a lot of evening's entertainment for the money. I remember enjoying Fielding's The History of Tom Jones, a Foundling, which is bawdy and very funny.

After reading a Joseph Conrad short story I thought he might be the finest author in the English language, and English is his third language, which he didn't learn until he was twenty-one.

But I have a challenge for all. Based on the subject matter, the works of Charles Nordhoff and James Norman Hall should be wonderful, riveting excitement. Try reading The Bounty Trilogy. (Mutiny on the Bounty, Men Against the Sea, Pitcairn Island) It's a great story. Just try to read the book(s). I wanted to love it. I just couldn't get into it. Read it or try to. I dare you!
 
I forgot about this one but recalled it after someone mentioned Lolita: Nabokov's considerably more challenging Pale Fire. It is one of the strangest novels one will ever read. It purports to be a 999 line poem by the poet John Shade, followed by a lengthy line by line analysis by his academic colleague and friend Charles Kinbote. The analysis quickly digresses into several different stories, challenging the reader to figure out what's really going on, whether Kinbote is telling the truth, and even who he really is. It's a favorite of mine but the prose is dense and deliberately confusing.
 
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Tolstoy, bloody Tolstoy. There's hours of my life I won't get back waiting for that damned prince whatshisface to die!
 
Mark Danielewski's "House of Leaves" is an experience and meant to be a challenge to read. There are inserts, backwards text, the story is all over the place, and so on. But it's a puzzle, not a novel.

I couldn't get through Gravity's Rainbow to save my life even though I wanted to enjoy it.
 
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