I think Moby Dick is the big one for me. It's the one I have the most trouble understanding how anyone else could possibly have enjoyed it. Only the book's reputation as a classic had me force myself through to the end. There were a handful of excellent paragraphs to be found (including the first), but it was like panning for gold: lots of mud and very little shine. If ever a book was made to be summarised by Reader's Digest, this was it.
Quite a few books in my log that get a score of 1 (Waste of Space) while getting 5 stars from others. It's a vast chasm of difference but usually I can see something that others might have found appealing or redeeming, even if I did not. So there's is usually a faint glimmer of understanding.
I have more trouble the other way. If I give a book 5 then I will forever wonder how someone else might give it a 1. 3 would account for different tastes, 2 if the person found the book truly annoying, but 1? And then I remind myself that other people not only have different taste, they also use different scoring rules.
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