Suggested by Janet:
How about, “What’s the worst ‘best’ book you’ve ever read — the one everyone says is so great, but you can’t figure out why?”
I have two answers for this one and both were read in college. One is Moby Dick. While I appreciate the themes of this book, I did not appreciate reading this one in any way, shape or form. The other one is Clarissa by Samuel Richardson. Holy Cow! This book was as big as a Norton Anthology, with those tissue thin pages and it was written all in letters. If I remember correctly, the first 500 or so pages lead up to the rape of Clarissa and then the following 500 pages show the aftermath of a woman whose virtue is forever tainted. That book was painful to both carry to class every day and to read.