I'm not a technical book person and I definitely threw this book across the room multiple times during this class. Hardest I've ever fought for an A-. It's not poorly written, I just struggle with math-y books.
One of the few books I kept from college and still pull it out once or twice a year when I need to look up something and refresh/relearn. Incredibly dense.
There are quite a few at the top of this list, and they vary based on subject. Are you speaking about technical books, or literature, or something else?
Regardless, the one that I spent a good year reading through multiple times was Farnsworth's Classical English Rhetoric. A brilliant book that challenged my knowledge of rhetoric and enabled me to hone my rhetorical skills. You can read it to learn or read it just for the awesomeness of the passages.
The Art of Computer Programming, volume 4a: Combinatorial Algorithms...and I am not suggesting I understand a meaningful fraction of it. It reminds me of how little I know. And in fairness I've been reading volume I by fits and starts since the late 1980's.
Critique of Pure Reason for similar reasons in another of my lifetimes. It's another book I'm not smart enough to criticize meaningfully.
Fiction, clearly Cormac McCarthy's The Road. As a parent it's just brutal to find a place to put it. Not necessarily my first recommendation among his novels, either.
Buddhist books whichs content cannot be fully understood as a concept and require subsequent meditation experience.
Most programming books are challenging to me as I'm more of a learning by doing guy and the content is usually either too abstract for me or in form of sample projects that dont teach much beyond mere replication.
I've never had any problem reading any book, obviously with the exception of ones written in foreign languages I don't speak at all. You can't fake it if you don't know anything at all. (trying to read chinese characters like Ezra Pound who squinted at them for obvious pictographic meanings.)
But there's one exception, my black horse.
I tried to skim the Bible (Old and New Testament), in multiple translations. Including easy ones, dumbed-down ones, ones for deaf readers, etc.
I thought that as literally millions of people have read this stuff for literally hundreds of years, and it permeates every part of western culture, it would be a walk through the park. Much easier than "more difficult" or specialized stuff.
This is not true. I found it absolutely horrific to try to read it from beginning to end. It's very difficult and basically I gave up, even in situations where I had no other reading material and absoluetly nothing else to do except drink some coffee and try to read it. I found the old and new testaments are unreadable.
This is not just because of the subject matter. For example (I've said this elsewwhere) I found the Qu'ran an incredibly easy skim. You can do it in an hour. (easily, and for meaning.)
This is just 566 pages triple-spaced with mostly blank lines, it's like 180 actual pages. It's incredibly repetitive. You can really stop on the parts that say something.
The whole thing doesn't say much, there's not all this useless geneology and history and names and such. It's easy.
Start skimming now and you'll be done by the time you get an answer to a quick email you just sent. 20-40 minutes if you're fast.
So it's not me. It's not hte subject matter. It's just that the old and new testaments are not the same at all. they're incredibly dense books that somehow made it into our culture while being totally unreadable sequentially. (for understanding.)
obviously it's fine to look up specific verses in. but as a book? Forget it. Even if you're stuck on an island with nothing else, it makes for the most impossible reading you'll ever find in a language you speak.
I would distinguish between challenging, because book is so overwhellming because of high level of proficiency required to read with understanding (eg. University paperbooks) so here I could say that a lot of was hard thus challenging. Other kind are challening because it change way you think about world and/or things and it's hard to apply knowledge you get, even you know it's right "view" like for me some of buddisth papers and Enchiridion by Epictetus. It's pleasure to read, but when you want to live in stoic way - yeah, then it's challenign.
Definitely loved Julian Jaynes. It's a "just so" story, but quite compelling and interesting - enough so to have a cult following.
Probably the most challenging/rewarding book I've ever read was Fuller's Synergetics. It offers an understanding of science and nature that is holistic in a way that is timeless and self-evident.
The definition of challenging I'm choosing to apply here is, stimulating, confronting, enlightening.
Martin Meredith's masterfully researched and written The Fate of Africa completely altered my worldview, and brought into sharp focus contemporary African politics. More broadly speaking, it brought clarity to global politics in general, and our human condition.
Finnegan's Wake is easier to read, in my opinion, because it isn't a linear novel. By its very construction, the non-deterministic "narrative" implores the Reader to leap, skip, and jump about as though lucid dreaming. John Bishop's introduction to the Penguin Classics edition (not my favorite edition, but definitely the best intro) provides a supporting context for this.
I recall a group of English professors had gathered ever Thursday for the last 3 years to get through Finnegan's Wake. Sometimes I wonder if such a work is something other than a book.
"Consilience" by EO Wilson is a challenging and rewarding book, especially considering it is thin, uses small words and short sentences. And has no math whatsoever. My recollection is I could only read a couple of pages at time without needing a nap.
And it was challenging because ...? Did it change your life or some other reason?
At a guess, I'd imagine many people would find the complete book challenging because of the unexpected material and viewpoints that can be found in sections of the Old Testament, like: https://www.biblegateway.com/passage/?search=Judges+19:22-30
On this topic, you may want to check out How to Read the Bible: A Guide to Scripture, Then and Now by James Kugel. It provides a historical overview of how the implicit and explicit interpretations of the old testament narratives have changed with respect to scholarship. Great read.
One can read the Bible on various different levels: as a historical document, a document specifically for you, and so on.
It has many surprises (like the example you gave). Heck, if the Old Testament was made into a movie, it'd be R rated.
My current favorite scripture is the origin of the pet. It's in Genesis 2:18-19. Adam was lonely in the Garden of Eden, so God provided Adam with animals for companionship. Adam gave a name to every one of his animal friends.
It's an endlessly fascinating book. I have many versions of it for study, but I prefer the King James.
It's literally the only book I've ever found unreadable (sequentially.) I tried really, really hard for weeks, and not just once. Multiple times over the course of different years.
man, forget it. It's easier to read a kernel dump.
I'm not a technical book person and I definitely threw this book across the room multiple times during this class. Hardest I've ever fought for an A-. It's not poorly written, I just struggle with math-y books.
http://www.barnesandnoble.com/w/introduction-to-algorithms-t...