Screw it, I don't finish shitty books, so I'm going to mention two from school:
Jane Eyre
What a FANTASTIC piece of shit. Jane spends the entire book reaching a stable point in her life, and running from it. She then (note: this was presented as a "strong female character" and had "great feminist ideals") spends most of the book bowing down to the man. Rather than standing up to views she disagrees with, she runs from them. Granted, the "run from a man who has the crazy 'ex'-wife in the attic instinct is probably right, but that is the exception. She then goes back to him. Her motivations are poorly planned, and it is evident the author was payed by the word. Descriptions are pages too long, for all the buildup of a character there is no payoff, etc.
I disagree that you have to judge a book based on the time it was written. Context is important, but a time difference doesn't excuse bad characters, horrid dialogue, and just poor writing.
Raisin in the Sun
Raisin makes some good points about racism and the quality of life of black in American cities in the early to mid 19th century. But I despised Walter's character so much. Rather than work to reach his goals, he puts his hopes in get rich quick schemes and cries about it when it falls apart. For all of the time he spends saying how he doesn't get respect, he does NOTHING to earn it.
I did like Frankenstein and Inherit the Wind, two books I remember from school. I also like Shakespeare, and have nothing against "classic" literature.
EDIT: Forgot about God-Emperor of Dune
It seemed to ramble and never really go anywhere except when you reached the "We found/he told the story about the plot-advancing McGuffin!" and killed my enthusiasm for the Dune series. Granted it was waning after Children, but God-Emperor felt like he just abandoned the universe he had spent so long to set up. I don't want to hear the jihad stories in the past tense, just as I read them in the future tense before, I want to experience them. It felt like the build-up lead to a period of time he had no intention of writing about, other than as a way of the character to say "That was/That's going to be crazy"