For the Iliad, at least, it depends enormously on the translation. The version that’s in the Britannica Great Books is so dry that if you drop your cell phone in a puddle, you can fix it by putting it in a plastic bag with the book. But I’ve read other versions that make it the gripping adventure tale that it’s supposed to be. I expect that this is probably also true of most other translated works.
James Joyce. A Portrait of the Artist as a Young Man. Awful melodramatic dreck.
I have no idea why Joyce is considered one of the greats of 20th Century English.
I remember it got rave reviews, everybody thought it was nearly the equal of A Hundred Years of Solitude. I read Cholera, thought it was OK but that was about it, and remember absolutely nothing about it. While I remember a great deal of Solitude despite not having read it in decades. I can still quote that marvelous first sentence almost verbatim.
I read Moby Dick on my ‘experience the classics outside of school’ phase. The book got so boring that I started skipping sentences, then paragraphs, then entire chapters. FFS, that book was horrible.
I fought my way through Mutiny on the Bounty. I compared it to swimming through wet cement. Incredibly dry and boring. I had to fight to read every word of the damn thing.
Confederacy of Dunces was horrible (is it considered a classic?). I’ve heard people go on on how wonderfully funny it was, but I never cracked a smile.
I first read the Iliad in junior high. I had just read Edward Fitzgerald’s translation of The Odyssey and loved it, but his translation of The Iliad hadn’t come out yet. I tried reading Richmond Lattimore’s translation (my mother used it for her college course), but I hated it. When Fitzgerald’s translation came out a few years later I immediately picked it up, and loved it.
Robert Fagle’s translations of The Iliad and the Odyssey for Penguin are pretty good, too. I have them on audiobooks, and just listened to them. I also just listened to the audiobook edition of Fitzgerald’s translation of The Iliad, and it still holds up. My gripe is that they changed all of Fitzgerald’s transliterations of the Greek back to the traditional ones, and I don’t like it. When Fitzgerald rendered “Ajax” as “Aias” it was harder to think of him as a can of cleanser.
Catch-22 is one of my favorite books, but I think it benefited from being read during the 1960s/Vietnam War/Cold War, when the never-ending absurdity resonated more. (Not that things are less absurd now, its just a different kind of absurdity.)
Hated Catch-22. Don’t think I even finished it.
The Sun Also Rises got a pretty negative review from me. Just very boring.
Sci-Fi classic They Dying Earth by Jack Vance was another one I had tough time getting through.
Those are my worst rated “classic” books. Of course there are many I’ve read that I didn’t love but aren’t among the worst. David Copperfield, however, (along with most of Dickens) I adore.
The only book I never got through on a school assignment was Lord of the Flies.
I would never have guessed. 
That’s a good point. I’ve often wished for a website or other reference that would spell out the pros and cons of the different translations available for a book I’m interested in reading.
I think it must have been Fitzgerald’s translation of the Iliad that I enjoyed, though it did take me a while to figure out that “Aias” was his writing of “Ajax”, and that “Aiantes” was the plural (there being two warriors by that name).
Barkis is Willin’, my only gripe (and it’s not a small one) with The Dying Earth is that nobody in those books seems to be good or heroic. Oh, there are a few, but certainly not Cugel, who gets an entire two novels devoted to him.
Heart of Darkness suffers from a vicious feedback loop where its simple prose and short length let it be dissected to death within the space of a few weeks of an English studies class. Similar short-lit books like The Pearl also fill this syllabus-ballast niche.
I read it in a college class swiftly, the obvious spotlighted symbolism made itself easily apparent, and I appeased the teacher with the obligatory expected commentary in my essay. I got a 4.0 out of the class, which is the only pleasant memory created by that book.
Iphigenia in Tauris by Goethe. This book is painfully hard to read. It’s a character drama based on characters that exist as Goethe wish they existed… But not a single one of them reads like a real person. The story is bereft of action or intrigue, and it’s fairly crazy. I worry I just didn’t get it, but… it was bad.
Funny you should mention that; I’m somewhere in my third (fourth?) reading of the series, and that’s where I got hung up this time around. I can confidently say that the first half of “Post Captain” is the most tedious and boring part of all 20 books.
If you can grind through to the point where they get to Toulon, it gets better from there.
Me either. A Portrait of the Artist as a Young Man and *Ulysses *were both f**king horrid.
Freshman year of high school I was in some advanced reading unit and we were supposed to read Les Miserables. I don’t think I even made it through the first chapter. Dull, dull, dull. If you want to teach someone to hate reading, assign that. I’ll take The Three Musketeers and The Man in the Iron Mask any day.
The books I remember annoying me most in grade school were Of Mice and Men and The Scarlet Letter. (Not in class, there was War and Peace, but that’s probably largely because my father bet me I couldn’t finish it in a week, and so I skimmed through it as quick as possible).
There were a few works and authors I liked even in English class. Shakespeare, anything by Saki, The Crucible. But for the most part, I was bored out of my mind.
I enjoy the thought of an associate of Ms. Austen, pulling on her the Harry Turtledove thing (slightly akin to Bilbo’s farewell speech) – “My dear Jane, if you were half as funny as you consider yourself to be; you would be twice as funny as you in fact are.”
Another vote for Catch-22. I literally not figuratively threw it away about half way through. I thought I was alone in my disdain for that book.
I did finish the movie, FWIW. Somehow it was less annoying. I guess I can thank Hollywood for their usual hack job of adapting novels.
I actually enjoyed Cooper a lot more after reading the Twain piece.
If A Confederacy of Dunces counts as classic, I nominate that. It is just tedious. If not, then the painful slog thru The Alexandria Quartet. The person who told me it got better the further you got into it was lying thru his teeth.
Regards,
Shodan