The unabridged Moby Dick remains my personal high bar of tedium. Even the unabridged Don Quixote, at over a thousand pages, didn't feel nearly as long. I pushed myself through - it helped a little that I'd read The Wreck of the Essex, the one written by a survivor of the real-life attack that inspired Moby Dick, and thus had a bit of an idea of the incident and general period whaling terminology - but... yeah. It was an "experimental" novel, if that helps at all.
The thing that made Moby Dick click for me and make the switch from tedium to actually interesting was when I realized my expectations were way off. Everyone knows the general premise via osmosis from pop culture: Guy is obsessed with killing a particular whale. What I expected going in was a narrative. Then it was like, "here's a chapter about soup, and here's a chapter about squishing your hands around in whale juice, oh... and here's one outlining all the kinds of "whales" known at the time, including dolphins," and I kept thinking "where is the story? When is it going to get back to the story?"
Finally I realized I needed to approach it like a documentary. Wanna learn interesting facts about whaling and whales, some of which are woefully out of date or inaccurate, but some of which are still relevant? This is the book for you. Want to be entertained by an obsessive hunt for ever-elusive prey? Watch roadrunner cartoons. (Seriously. Roadrunner cartoons are awesome).
Once I changed my expectations, I discovered I actually like Moby Dick after all.
.....
My challenge book is "A Confederacy of Dunces." I've read the doggone thing twice; so many people adore it that I thought perhaps I missed something the first time around. The second read was after I'd spent enough time in New Orleans to actually recognize the story's settings and references, which I thought might increase my enjoyment.
I really, really WANT to like it, but there's something about it that just doesn't resonate with me. It makes me a bit sad that I don't get the enjoyment from it that others do.