Since I've been into reading the Classics for the last 2-3 years, and unfortunately, haven't set foot in a library or book store to peruse for pleasure in that same amount of time (I usually order series paperbacks of the classics through Amazon and have them sent to me), I can not recall a book that I judged by its cover as "good" and after reading it found out it wasn't so fun to read.
However, I have had parallel experiences with a book's reputation vs. my actual enjoyment of said book. The most recent instance of this was Oscar Wilde's, The Picture of Dorian Gray. I thought, "how can I go wrong with Oscar Wilde, one of the 'Classics'?" Well, after a good try (we're talking what was for me, painful trudging through half the book) I just had to stop reading it. I've never read Wilde before Dorian Gray, and I plan on giving him a go with something else he's written sometime later - and it's not like I didn't like some of his style - his descriptions were lovely, but I just couldn't take the random shifts in person throughout what I felt was too short a section, or paragraph even. (<--that was a run-on sentence...sorry!)
As a whole, the Classics, suffer the "don't judge a book by its cover" phenomenon. Since so many are mass produced as part of a series, the covers are quite bland (see Doran Gray above).
It is very rare for me to not finish a book once I've started. Guilt engulfs me. I am stubborn and will keep on reading, even if I find the material disappointing. However, there are two more books I can add to my list of book I feel guilty about not finishing reading:
Anne Rice's, The Witching Hour (and I LOVE the vampire series so much!)
Clive Barker's, Imajica (when I needed to take notes, I had to stop - I know...)
Maybe one day I will try finishing them.
