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.

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.

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!

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. 

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.

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.

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.

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.

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.

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.

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.

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!)

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.

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."

The most difficult book I ever read was Pagan and Christians [a history of early Roman religions] by Robin Lane Fox. I didn't understand a word of it until pages 698 and 699--Part II started on page 700. If you read it and have never read archaeological works before, allow me to suggest you read pages 698 and 699 first, then go back to page 1. You may fare better than I did. Also Lane uses colons (:) in a fashion I was unaccustomed to. Usually, explanatory or additional information comes after the colon, but Lane wrote in the reverse: he put the detailed explanatory information first, then followed with the broader statement. It would be something like this:

Lane put the detailed explanatory information first then followed with the broader statement: usually, explanatory or additional information comes after the colon, but he wrote in the reverse.

It was fine once I caught on--somewhere around page 525. I was well used to his style by the time I got to page 698. Great book. I've read it a second time since that first go round (and yes, I refreshed my memory of pages 698 and 699 before embarking from page 1).

I would have to say that the most challenging book I've read to date has been House of Leaves by Mark Z. Danielewski. He's such a talented writer! The book is not difficult because of register, but because of the layout. Some pages are written on a diagonal, some written in circles, some with only a few words. There are pages upon pages of appendices, indexes, and footnotes - some of which come from viable sources while others were made up for the purposes of the story. The jumping around and flipping back and forth and looking things up online is what will really wear you out!

I agree that defining the word "challenging" is the key here. Many people have commented on Ulysses. I have started to read it but frankly Joyce is a little too verbose for me. Rather, the stream of consciousness and literary quality goes on for so long that by the time the rambling ends i have completely forgotten what I've read.

I found the Scarlet Letter to be as dry as week-old bread.

In the "it's just painful" arena, my vote goes to Flannery O'Connor. Recently I wrote an indepth study guide for a non-related site. By the time I was done, I was so irritated that I wanted to toss the book across the room. Not very professional so instead I told my editor that if he ever had to read O'Connor or take a bullet...take the bullet.

I would say Ulysses by James Joyce, but I'm not sure this counts, as I've never actually made my way through it, although I've tried several times over the years. My plan is to wait for a time when I'm immobilized from a skiing accident and have to spend several weeks in bed with my leg in a cast suspended from the ceiling. Maybe then I can read it, since I won't be able to get up and walk away. In truth, this isn't going to happen since I don't ski, but it's always good to have a plan!

I have a hard time with anything by Joseph Conrad.  I know that his language is magnificent, that his themes are profound--but quite honestly, I don't know what he's talking about much of the time.

If you're looking for some Conrad that's a bit more accessible, I recommend a story called "Il Conde."  It's classic Conrad, but comprehensible.

I think for me American Psycho - not because of the language, but just because of the sheer violence and grossness of the content! I really couldn't finish it as it was just too disturbing. I guess if you want a book that was challenging because of its language, Ulysees by James Joyce has to be the big one - the bane of every English Literature student in the UK!

In reply to post 15: I absolutely adore James Joyce's Ulysses.  I spent an entire semester in college working through it, and I'm glad that I did--I love every page of it.  It required so much supplementary reading (Reading Joyce's Ulysses, Allusions in Ulysses, The New Bloomsday Guide to Ulysses, etc) that it was overwhelming at times, but the payoff was so great that all the hard work was completely worth it.

I do have to say, though, that I'm not sure I would have gotten through it on my own, and I certainly benefitted from having a professor who offered a course just on this novel (although we obviously had to read Portrait first in order to meet Stephen Dedalus), since we had so much time with it.

(As an aside, I remember calling my mother--who is also an English teacher--and crying while I was trying to read Spencer's The Faerie Queen for a Brit Lit course in college.  I don't remember specifically why I was so frustrated with it, but I'd say that was my worst experience with a work that I was required to read.)

How do you define "challenging"? If you mean a book that was difficult to read because of its style or vocabulary, then it has to be Charles Dickens's Hard Times. I never got past the first chapter. If you define "challenging" as a book that just did not interest me, but I was required to read for class, then that book would be Billy Budd--just dreadful! If you mean a book that challenged me to make a change in myself, then it most definitely would be the Bible.

Speaking of Joyce, has anyone ever tackled Ulysses?  That's one, along with War and Peace, that I'm saving...or avoiding, depending on how you look at it!  I'd have to agree with others that Moby Dick was probably the hardest book I've ever tackled (it seemed to move so slowly), followed closely by Peter Mathiesson's The Shadow Country. Actually, now that I think about it, they're both books about a futile hunt.  Maybe it's the plot I can't take.

Like several others here, I struggled mightily with A Portrait of the Artist as a Young Man. I've been reading as long as I can remember (I read my first 1,000 page novel when I was ten), and I usually attack challenging texts with vigor. I loved Shakespeare, loved Wuthering Heights, The Scarlet Letter, all those ones that students usually have trouble with in school. I even love non-linear, stream-of-consciousness narratives...but Joyce definitely posed the ultimate battle for me.

I would have to say that, at the time, my first attempts at Heart of Darkness and Moby Dick were some of the most frustrating reading experiences I've had. I was at a complete loss as to even a basic plot line in these works, largely because of the vocabulary and the structure of the narratives. Probably not surprising, these are two of the works I now most admire in literature. The challenge of these works and the multiple readings they required made me a better reader. It's easy to say that now, but at the time I would have gladly thrown these books out the window!

I just can't get past all verbage in Dickins, so I would have to say Bleak House or David Copperfield. It wasn't that the story was hard, but it just took so long for things to happen and to discover the significance of things that I would lose track of information and need to skim back, which made the reading all the longer and more challenging.  I liked his shorter novels, in particular, Oliver Twist so I can say I am a Dickins fan, but I am selective.

As far as classics go, anything by Faulkner or James gives me fits.  I also remember the first time I read The Grapes of Wrath (of course, I was in middle school, so that is a telling factor in itself), and struggling to read past the turtle crossing the road chapter.  I so wanted to catapult that turtle...as I have grown in appreciation for author's purpose, however, I can handle that chapter a little better and giggle when my students have the same reaction.

The Shack also challenged me quite a bit.  I had to read and re-read several sections of that book which challenged by belief system and made me think about not only what was being communicated, but also if I agreed with it or not and why.  It was intriguing, and made me feel a little dumb, I'll admit.

As an undergraduate I remember having a hard time reading The Ambassadors by Henry James. I had loved Portrait of a Lady and other shorter works by James (Washington Square, Daisy Miller, The Turn of the Screw), but I could not get into Strether's European journey and his quest for his wealthy and widowed fiancée's son Chad. The book put me off James's so called "major phase" for a long time.

A Portrait of the Artist as a Young Man was an excruciatingly difficult read for me. I'd never have selected this novel as leisure reading. I had to read it for an English major class. Normally I breeze through reading assignments, whether fiction or nonfiction, but Joyce was a barrier that I found difficult to overcome. I have never attempted to read any other of Joyce's works.

The American author that I find least accessible is Faulkner. I had to read "The Bear" for a college freshman English class, and it colored my perception of all subsequent Faulkner assignments.

Mine is Blindness by Jose Saramago.  It took me ages to work through the prose because it all just runs together.  Plus the characters are not named and are only labeled by their role in the story.  Finally, some of the scenes are hard to handle (the level of sexual violence in the book is extreme and I had to put the book down for a week before continuing which is surprising because I have never been this troubled by a book before).

I spent a good deal of time tussling with Moby Dick for a tutorial at uni to be truimphant as the only student who had actually read it.  It was certainly worth the effort. I keep trying to read The Bone People by Keri Hulme but the layers of Maori symbolism are still too much for me.

Novels that are read in youth seem more challenging as it seems that experienced readers can  bring something to the novel.  Once Saul Bellow was asked why there are no more great books written.  He replied, "There are no great readers to buy them."

Among the challenging ones, Moby Dick was certainly one, but having reread it many years later, did, indeed, help to increase comprehension.  James Joyce's Portrait of the Artist as a Young Man with its stream-of-consciousness bewildered one 20 year old: "What was that about?"  Virginia Woolf's works (To the Lighthouse) and those of D.H. Lawrence (Sons and Lovers) are formidable at times, too.

It does seem that some novels require at least two readings, if not more....

I guess the most challenging for me was The Gulag Archipelago.  In fact, many Russian authors in addition to Alexander Solzhenitsyn are difficult for me.  Tolstoy should be on that list and War and Peace, because I had such a hard time finding the time to actually finish it.  Moby Dick by Melville too.

I think I'd have to define the word "challenging" first.  If you're referring to the difficulty of getting through a boring book, it'd have to be Absalom! Absalom! or A Portrait of the Artist as a Young Man. If it was a book that challenged my personal beliefs, it would be Brave New World.  I also might take "challenging" to mean thought-provoking, I would have to say it was A Clockwork Orange.

Every year, I feel as though reading The Scarlet Letter is an accomplishment.  I always find new insights and observations which challenge my thinking and increase my appreciation for Hawthorne's use of language.  I think the challenge for me is to make this complex piece of literature meaningful for students who want easy and modern and direct--and to do so without any gimmicks or tricks.  Just plain, old-fashioned reading and appreciating.  On a personal level, Who's Afraid of Virginia Woolf was nearly the death of me one summer early in my reading life, and I've never tried it again.

I had a hard time with The Sound and the Fury by William Faulkner.  The first section of the novel is written from the perspective of Benjy who has a severe mental handicap.  The narrative is hard to follow and quite disjointed. It was difficult getting through that first section, but the book was well worth reading.