What is the most challenging book you have ever read?I have several. As far as depth and vocabulary I had a hard time with Bleak House by Charles Dickens. It was like I could almost sense his state...

What is the most challenging book you have ever read?

I have several. As far as depth and vocabulary I had a hard time with Bleak House by Charles Dickens. It was like I could almost sense his state of mind when he wrote it.

Wuthering Heights took me a bit of time.

The Blind Watchmaker was very interesting, because of its content, but I think ultimately no book could possibly be anything less than a personal adventure.

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80 Answers

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Noelle Thompson | High School Teacher | eNotes Employee

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Oh, absolutely The Sound and the Fury or any later work by Faulkner.  I remember my jaw actually dropping when I found out in AP Literature what "really" happened to poor Benjy.  Oh my, innocence at its best.  I'm afraid my reaction to this novel began my dislike for modern literature.  Is it because the South is portrayed in a state of disintegration?  Maybe. ... but then again, that was at a time when I thought living like Maria Von Trapp was possible, ...

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kaitbird | Student, College Freshman | (Level 1) Adjunct Educator

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The most challenging book I have ever endeavored to read was definitely Finnegan's Wake by James Joyce. We attempted only a few pages of it in my Literary Culture of Modern Ireland class but each line (and sometimes even each word) was a puzzle crafted by Joyce that we needed to solve. It was a strange experience and made me look at literature in a new light. It showed me how many different implications and connotations a single word can have and how drastically its interpretation this can change the reader's perception. It is now one of my goals to make it through the entire book, reading even just one page per day for a sustained period of time.


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litteacher8 | High School Teacher | (Level 3) Distinguished Educator

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I think books can be challenging for different reasons.  I believe that the most challenging books are books in which the ideas themselves are challenging, more than the language itself.  I sometimes struggle with the vocabulary of an older book or a technical one, but I consider the books that make me reconsider my most deeply-held beliefs to be the most challenging.  I personally found The Road very profound and meaningful, for example, even though the text itself is easy to read.  I teach my students that even simple books sometimes explore deep truths.  A book may not be written at a high reading level or contain a lot of advanced vocabulary, but if it makes me stop to think and question myself I consider the book challenging.

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stolperia | (Level 1) Educator Emeritus

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Without question, the most challenging book I have ever read (and continue to read) is the Bible.  I find it challenging on numerous levels: reconciling the meaning of phrases rendered differently in various translations; trying to determine how descriptions of archaic practices may relate to contemporary activities; struggling to understand cultural traditions and expectations that shaped perceptions and reactions in Biblical times; most of all, seeking how to apply the wisdom and examples it contains in my own life.  I am looking forward to having time and opportunity to undertake in-depth study of the Bible as a piece of literature that has stood the test of time, as well as the centerpiece of my religious faith!

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tolchowy | High School Teacher | (Level 1) Adjunct Educator

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What is the most challenging book you have ever read?

I have several. As far as depth and vocabulary I had a hard time with Bleak House by Charles Dickens. It was like I could almost sense his state of mind when he wrote it.

Wuthering Heights took me a bit of time.

The Blind Watchmaker was very interesting, because of its content, but I think ultimately no book could possibly be anything less than a personal adventure.

  Reading Lolita in Tehran by Azar Nafisi was, by far, the most challenging novel I have ever read. To truly appreciate the text you needed to have a knowledge of a number of texts found in each of the sections of the novel: "Lolita", "Gatsby", "James", and "Austen".

Under the "Lolita" section you needed to have read Lolita, One Thousand and One Nights and Invitation to a Beheading.  Under the "Gatsby" heading you needed to have read The Great Gatsby and Mike Gold's works.  Under the "James" section you needed to have read Daisy Miller and Washington Square.  Finally under the "Austen" section you needed to have read Pride and Prejudice. 

While I had read many of the texts referred to in the novel, some I had not read for a number of years so could not recall every reference and, in the case of the novels I had not read, I did not understand the reference. 

This is a novel that would be enjoyable to read as the foundation for a Univesity course with the other texts being prescribed reading as well. 

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mitchrich4199 | High School Teacher | (Level 1) Associate Educator

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I would have to say, like many of my counterparts, that Portrait was the most challenging book that I've read and finally understood. I've read Joyce's Ulysses as well, but when I say I've read it, I can only say that in the physical sense. I've read every word of it, but I haven't understood much of anything from it, yet. This is a novel that I need to go back and read and study. I'd like to take a class on it someday as well. Portrait provided a difficult challenge for me and I feel that I can say that I "conquered" it in as much as I can now discuss it skillfully and effectively, while still learning about it every time I use it in class.

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psmortimer | (Level 2) Adjunct Educator

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I'm sure there are more than the first two that come to mind.

Ulysses has to be one. I've never been fond of the "literary" style when it is stretched out to the extreme. Joyce is known for his love and use of words. However, I find that he tends to go on about a particular minor point/subject/character for so long that I have completely forgotten what I've read. I never did finish it.

The other has to be The Scarlet Letter. I like that period in history but the writing was so dry that I couldn't get through it.

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jashley80 | High School Teacher | (Level 1) Assistant Educator

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I can think of many challenging books, though they were challenging for different reasons based upon the age at which I tried to tackle them. Reading Rushdie's The Satanic Verses as a sophomore in college was challenging because I began it while on a small plane flying through a thunderstorm (in the opening, men are falling from the sky)... it was a challenge to continue reading because I kept associating it with the anxiety I felt during that very long 45 minute plan trip in the storm.

I could not make myself read past page 2 of Dickens' A Tale of Two Cities during and even after college because the style of writing lulled me to sleep - it was only listening to it on tape that worked for me. However, I had no difficulty reading Beowulf or other Anglo-Saxon and Medieval texts because the history and plots appealed to me.

The Wasteland and "Four Quartets" were challenging for me my sophomore and junior years in college (though "The Love Song of J. Alfred Prufrock" did not seem so in high school), but I enjoyed them so thoroughly that I embraced the challenge of deciphering the allusions and sifting through the imagery. I actually plan to keep in mind the poetry of T.S. Eliot as a thesis option when I work for my Ph.D.

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kmalone614 | High School Teacher | (Level 2) Adjunct Educator

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The most challenging book I have ever read is definitely Nightwood by Djuna Barnes. I don't remember much about it, because I'm not sure I understood any of it. I had to read it for a Fiction class during my undergraduate work, and it was my introduction to post-modern literature, with which I still struggle.

I noticed many of the posts also mentioned A Portrait of an Artist as a Young Man by James Joyce, which I would also agree is difficult. Because of my struggles with this, I have never attempted what is supposedly the most difficult book around, also by Joyce - Ulysses.

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celtic1108 | College Teacher | (Level 2) Adjunct Educator

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James Joyce's Ulysses was my most challenging book. I tried to read several time on my own and never made it through. Finally, while in grad school, I took a James Joyce class. With the class discussion and several supplemental books, I was able to read the book in it entirety and understand it! It truly is a masterpiece. I love Joyce's playfulness throughout the work. This book is a major hurdle to tackle on your own. I highly suggest a book club for support. If anyone would like a few supplemental material for Ulysses, just let me know. I have a few that I could suggest. Maybe we should start a James Joyce Discussion Group focusing on Ulysses? Next, I will tackle Finnegan's Wake.

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coachingcorner | High School Teacher | (Level 1) Senior Educator

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Ulysses by by James Joyce gave me a run for my money - and still does (I still pick it up to finish it one day!) The novel is well known, I think, for being an intellectual and literary challenge, and for any literature student who needs stretching I would recommend it entirely.

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booboosmoosh | High School Teacher | (Level 3) Educator Emeritus

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I am sure the list is a long one, made up of the books by which I was challenged that I actually finished, and the books that gained the upper hand, which still glare of accusingly at me from the book shelf.

I think the book that really made me crazy was James Joyce's Ulysses. I must admit that I was proud to have finished it (it was part of a college course), but have to say that I would never want to read it again, and must give a lot of credit to my professor who was highly enthusiastic and refused to leave his students behind when we stumbled...often.

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mamape | High School Teacher | (Level 1) Adjunct Educator

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I love Dickens, and pretty much anything Russian as I studied Russian too, but I have a lot less patience in the face of absurd writing, or stream of consciousness.

Ulysses and Catch 22 are both languishing unfinished on my shelf, whilst I indulge in more appealing reads! (I will finish them one day, purely from shame!)

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namurchi | High School Teacher | (Level 1) Adjunct Educator

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I found As I Lay Dying very difficult.  It was my first Faulkner read and many pages left me so bewildered that I laughed out like a lunatic.  I told the assigning professor that Faulkner's writing sounded like pots and pans being banged together.  I am still not sure if I will ever tackle another, but I do enjoy being surrounded by his legend in my home town.

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Karen P.L. Hardison | College Teacher | eNotes Employee

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If you mean book of fiction, that would be Tolstoy's War and Peace. I read it the summer before my senior year in high school. I actually had to resort to putting a chair in front of my mother's pull-out wooden kitchen cutting board so I could read it (the board was higher than the table and made hours and hours of neck bending easier on me) because it was too heavy for me to hold. One day when I was about half-way through she asked me how I liked it. Without looking up from the page, I said, "I don't understand a word of it--I have no idea what he's talking about--none whatsoever." She said, "Then why are you still reading it?!" I said, "Because it's so beautiful. The words are so wonderful. Even if I don't know why he is saying what he is saying, I want to keep reading the beautiful words ... and maybe it will all make sense at the end."

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