Tuesday, May 6, 2025

Most Challenging Books

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Let's be controversial. What's the most challenging book you've ever read? Which book do you think is the densest, most confusing, most tedious book ever? It's probably a philosophy book. I had to read so much philosophy in college. I spent four years being chronically confused.

I was tempted to fill this list with philosophy books, but I decided to branch out a bit. Here are 10 books that forced me to ride the struggle bus. They're confusing, or boring, or rambling, or just really freakin' long!




Most Difficult Books Ever





Crime And Punishment by Fyodor Dostoevsky




Raskolnikov, a destitute and desperate former student, wanders through the slums of St Petersburg and commits a random murder without remorse or regret. He imagines himself to be a great man, a Napoleon: acting for a higher purpose beyond conventional moral law. But as he embarks on a dangerous game of cat and mouse with a suspicious police investigator, Raskolnikov is pursued by the growing voice of his conscience and finds the noose of his own guilt tightening around his neck. Only Sonya, a downtrodden sex worker, can offer the chance of redemption.


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War And Peace by Leo Tolstoy




At a glittering society party in St Petersburg in 1805, conversations are dominated by the prospect of war. Terror swiftly engulfs the country as Napoleon's army marches on Russia, and the lives of three young people are changed forever. The stories of quixotic Pierre, cynical Andrey and impetuous Natasha interweave with a huge cast, from aristocrats and peasants to soldiers and Napoleon himself.


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The Wind-Up Bird Chronicle by Haruki Murakami



In a Tokyo suburb a young man named Toru Okada searches for his wife's missing cat. Soon he finds himself looking for his wife as well in a netherworld that lies beneath the placid surface of Tokyo. As these searches intersect, Okada encounters a bizarre group of allies and antagonists: a psychic prostitute; a malevolent yet mediagenic politician; a cheerfully morbid sixteen-year-old-girl; and an aging war veteran who has been permanently changed by the hideous things he witnessed during Japan's forgotten campaign in Manchuria.


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The Sound And The Fury by William Faulkner




The Sound and the Fury is the tragedy of the Compson family, featuring some of the most memorable characters in literature: beautiful, rebellious Caddy; the manchild Benjy; haunted, neurotic Quentin; Jason, the brutal cynic; and Dilsey, their Black servant.


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One Hundred Years Of Solitude by Gabriel García Márquez




One Hundred Years of Solitude tells the story of the rise and fall, birth and death of the mythical town of Macondo through the history of the Buendiá family.


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Atlas Shrugged by Ayn Rand




Atlas Shrugged is the astounding story of a man who said that he would stop the motor of the world—and did. Tremendous in scope, breathtaking in its suspense, Atlas Shrugged stretches the boundaries further than any book you have ever read. It is a mystery, not about the murder of a man's body, but about the murder—and rebirth—of man's spirit.


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The Canterbury Tales by Geoffrey Chaucer




The Knight, the Miller, the Friar, the Squire, the Prioress, the Wife of Bath, and others who make up the cast of characters— including Chaucer himself—are real people, with human emotions and weaknesses.

If we trust the General Prologue, Chaucer intended that each pilgrim should tell two tales on the way to Canterbury and two tales on the way back. He never finished his enormous project and even the completed tales were not finally revised.


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To The Lighthouse by Virginia Woolf




The serene and maternal Mrs. Ramsay, the tragic yet absurd Mr. Ramsay, and their children and assorted guests are on holiday on the Isle of Skye. From the seemingly trivial postponement of a visit to a nearby lighthouse, Woolf constructs a remarkable, moving examination of the complex tensions and allegiances of family life and the conflict between men and women.

As time winds its way through their lives, the Ramsays face, alone and simultaneously, the greatest of human challenges and its greatest triumph—the human capacity for change.


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A Portrait Of The Artist As A Young Man by James Joyce




The portrayal of Stephen Dedalus's Dublin childhood and youth, his quest for identity through art and his gradual emancipation from the claims of family, religion and Ireland itself, is also an oblique self-portrait of the young James Joyce and a universal testament to the artist's 'eternal imagination'. Both an insight into Joyce's life and childhood, and a unique work of modernist fiction, A Portrait of the Artist as a Young Man is a novel of sexual awakening, religious rebellion and the essential search for voice and meaning that every nascent artist must face in order to blossom fully into themselves.


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Moby-Dick by Herman Melville




In part, Moby-Dick is the story of an eerily compelling madman pursuing an unholy war against a creature as vast and dangerous and unknowable as the sea itself. But more than just a novel of adventure, more than an encyclopedia of whaling lore and legend, the book can be seen as part of its author's lifelong meditation on America.


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What's the most difficult book you've ever read? Was it worth the effort?






12 comments:

  1. Yep, classics can often be "difficult" reads. I struggled with Tolstoy.

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  2. Probably Upton Sinclair's The Jungle.

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  3. I have read #1,2,5,8,9 and 10. And yes, they are difficult though I always enjoy that. The most difficult ones I read are probably Ulysses and The Satanic Verses.
    Every time I see To the Lighthouse, I have to smile because we read that in a book club. We had just finished a very large book and someone said, oh, the next one is going to be easier, it's so short. I warned them that it would take them just as long to read it. Most of them didn't believe me and couldn't finish it in time.

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  4. I was an engineering major, so I will go with Organic Chemistry. Oddly enough, I am not surprised by this list.

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  5. I think that if a book is too challenging, I toss it. And you know I am not one to DNF lightly! But man, nothing makes me crankier than a book trying to make me feel dumb. When I was 10, my dad made me read David Copperfield. Now THAT was the driest behemoth of drivel I've ever had the displeasure of reading. I mean, I still have memories of sitting at my desk, opening the thing, and my eyes just glazing over. I probably "read" each page 2-3 times, but absorbed almost nothing since it was all such a complete bore. I am sure there is plenty of junk that went over my head at 10, but I honestly doubt I'd feel a ton differently now.

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  6. I've read more of these than I thought I would have. I liked both Moby Dick and Crime and Punishment.

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    1. I gave up Atlas Shrugged, too, but not before it exposed to me how dangerous her philosophy was to humanity.

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  7. I disliked Crime and Punishment but loved War and Peace! Those are the only books on your list that I've read. I also read the Lord of the Rings trilogy when I was 12 and struggled. I was convinced for the longest time that I didn't like Tolkien, when actually I just wasn't ready for the Lord of the Rings lol

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  8. I've tried to read Crime and Punishment, War and Peace and Atlas Shrugged (though I did finish The Fountainhead). I finished One Hundred Years of Solitude and The Canterbury Tales (for AP English in high school). I plan to go back to C & P one of these days as I think if I put in the effort it'll be rewarding. But the others... not really that fussed unless I have a reason at some point. I loved One Hundred Years of Solitude though. I found it challenging at the beginning to get used to and keep track of all the characters, but once I had it, it was such a beautiful and immersive read. It's one of the books that launched me into a love of magical realism that's been very rewarding! Of books I've read, I'd say that Ducks, Newburyport was challenging (though I ended up loving it when I listened to the audio). And I tried to read Ulysses once, and couldn't even understand where it was set, let alone anything that was going on in it. So I gave up. Great post!

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  9. I always feel proud of myself when I finish reading a challenging book. I usually end up liking the books, too.

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  10. I also studied philosophy and I don't know a single person who wasn't perpetually confused on the course. I realised the work all boiled down very clever philosophers being confused about life and the world and trying to make sense of it, which is when I started to accept that it was ok to be confused by the subject as a whole 😂 I don't think I've actually read a book that truly challenged me as I'm always scared of them. That's why I started the Classics Club challenge, and have made the brave decision to put Crime and Punishment on my list 😳

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