I still can't think of a book I hate with passion, but The Last Days of Socrates (Euthyphro, Apology, Crito, Phaedo) comes close. Plato and I differ on a number of basic philosophical grounds, but that's something I can overcome. It's his use of dialogues as tools for character assassination that I can't stand.
There's something hypocritical about the lauded position Plato holds in so many academic institutions, when Plato ruthlessly targeted the sophists because they charged money to their students.
Anything Shakespeare, and antigone
In my opinion you shouldn't have students read a play without seeing it preformed first. When it comes to Shakespeare I believe the only two plays I've actually enjoyed reading were Othello and MacBeth, but there are numerous ones I've enjoyed watching: The Tempest, A Midsummer Night's Dream, Much Ado About Nothing, Henry V, and probably one or two others I can't think of off the top of my head. I don't mind Romeo and Juliet, but it really is overdone. The closest I've ever come to enjoying Hamlet was The Canterville Ghost, it's just not my cup of tea.
I've read Sophocles, and I've seen Oedipus Rex preformed. Neither did anything for me.
I spend about 3-4 hours a day in traffic on the way to and from work, so I've taken to listening to audiobooks as a way to make the time feel slightly less wasted. Our library has a poor selection, so a few weeks ago I was forced to take out The Swan Thieves by Elizabeth Kostova. I was pretty lukewarm on The Historian, but beggars can't be choosers so I gave her second book a shot. Wow. I've never stopped a book without finishing it, but I came closer than ever with that thing. No part of it was believable. The author had no idea how to write believable male characters, so EVERY SINGLE CHARACTER came across as bookish woman in her mid 40s. She goes off on ridiculous tangents--do we really need to know what every character's childhood was like, and somehow, with all that information dumped on us, the characters lack any of the kind of details that would make them feel like real people. It got slightly better at the end, but that might have just been me feeling proud of myself for successfully enduring something so awful. I've read books where I get angry at the author, but I think this was my first experience where I actively pitied the author. I could write a book of equal length about all the problems I had with that thing. Good lord.
It's a shame that so many common criticisms of her first book didn't result in any improvement with the second.
There are authors that I have difficulty reading, but I'm willing to say we're just not compatible. Umberto Eco is one example, for some reason even getting through a few pages of one of his books is like pulling teeth, even though he seems like an ideal author for me. But Kostova . . . I recognize that some people enjoy her work, and that's great, but it really does seem badly written.