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What's the most messed up book you've ever read?

Dude get arrested and prosecuted. Literally could not even figure out what he was charged with. Bureaucracy, bureaucracy, red-tape. He tries. The system laughs. He tries. "You hurt your own case by failing to participate." He tries. And looks more guilty in the process.

Helpless. Incomprehensible.

He eventually gets executed.

Never even found out what the alleged crime was.
 
I was gifted The History of Torture by Daniel P. Mannix by a friend for a secret Santa thing. Fun for a history major that also plays death metal. It's old and I'm sure that at least some of the details are outdated but it's a fun read.
 
"S" by Doug Dorst & JJ Abrams (yes, the movie guy). Not because it's a grotesque plot or anything, but because it's two stories in one. The premise is that you're reading a book called "Ship of Theseus," borrowed from the local university library. There's a complete story within the lines. However, in the margins, there are also handwritten notes between a professor and a student who keep borrowing the book and even leave photos, postcards and newspaper clippings for each other (yes, there really are said things as inserts on given pages), which makes up a whole second story.
 
Two words. Clive Barker. Picked Scarlet Gospels up from a library as a teenager to read on a family road trip expecting a decently dark but simple horror story, my unprepared soul not realizing who Clive Barker was. I was in the backseat, family in the front seat, some cheerful pop music on the radio as each paragraph got worse and worse.
I quickly put it down after the prologue. Only look it up on your own discretion, but as a fair warning it's bad. REALLY bad. You will be changed.
 
Kingdom's Bloodline by Masterless Sword.

It is a webnovel being translated by some team, think EndlessFantasy are/is Translator(s)

I only read a few chapters. Fifteen or so.

But even those few chapters brought up orphan abuse and graphic murder to even make me pause in my reading of it.

Basically so far it is dark fantasy. I am still trying to figure out the 'timeline' of the story. I think it falls under the Medieval period or maybe Victorian(due to orphanages and 'gangs,' and police forces) Again I haven't gotten that far after the violent material involving the first few chapters, but most people have been using cold steel weapons in it.
 
Probably Tender is the Flesh.

...I have The Wasp and The Trial on order right now at my book store, ahaha-
Tender is the book that would make me veggie if I had it in me. Maybe it did for a week.
Cows, also.
Garlic Ballads.
 
The Virgin Suicides, by Jeffrey Eugenides

Lot of unreliable narrator stuff going on in the book, but the way in which the titular events happen are not exactly pleasant. At least from what I recall
 
Not sure these are the *most* messed up I've read, but Things Have Gotten Worse Since We Last Spoke, Motherthing (which I finished yesterday), and Borrasca (yes, the creepypasta) immediately come to mind.
 
A bit of weird one, but hear me out:

I read (a translated version) of the Malleus Maleficarum, whitch translates to "The Hammer of Witches", at uni
First published in 1486, it is a practical guide on how to identify, capture, torture an dispose of witches.

It's pretty grim, but what makes it so messed up is that it is not fiction.
At the time, anyone found to be heretical, strange or diffrent were often persecuted, and burned at the stake.
This document, written by a member of the clergy, greatly encouraged this to apply to witches.
Thousands of people in europe, mostly women, lost their lives to the witch hunts
 
I don't read a lot of messed up books, but the third book of the Malazan series had crazy women raping dying soldiers on the battlefield, to get pregnant and give birth to "Children of the dead seed". Oh and cannibalism. Lots of cannibalism
 
A bit of weird one, but hear me out:

I read (a translated version) of the Malleus Maleficarum, whitch translates to "The Hammer of Witches", at uni
First published in 1486, it is a practical guide on how to identify, capture, torture an dispose of witches.

It's pretty grim, but what makes it so messed up is that it is not fiction.
At the time, anyone found to be heretical, strange or diffrent were often persecuted, and burned at the stake.
This document, written by a member of the clergy, greatly encouraged this to apply to witches.
Thousands of people in europe, mostly women, lost their lives to the witch hunts
I did a 15-page term paper in grad school on early-modern European witch hunts. The good news is that evidence indicates that many contemporaries of the author of the Malleus Maleficarum viewed him as a bit of an unhinged nutter. If you're interested in historical witch hunts I highly suggest Witch, Wicce, Mother Goose: The Rise and Fall of Witch Hunts in Europe and North America by Robert Thurston.
 
Blood Meridian, or the Evening Redness in the West by Cormac McCarthy. It's an existential western that explores the lengths of mankind's violence and casts the myth of the American West as a hellish apocalypse, basically. It gets  rough. It's  also probably the most beautifully written book I've ever read and I'd put it somewhere in my top five.

Here's one of my favorite quote:
"The truth about the world, he said, is that anything is possible. Had you not seen it all from birth and thereby bled it of its strangeness it would appear to you for what it is, a hat trick in a medicine show, a fevered dream, a trance bepopulate with chimeras having neither analogue nor precedent, an itinerant carnival, a migratory tentshow whose ultimate destination after many a pitch in many a mudded field is unspeakable and calamitous beyond reckoning.

The universe is no narrow thing and the order within it is not constrained by any latitude in its conception to repeat what exists in one part in any other part. Even in this world more things exist without our knowledge than with it and the order in creation which you see is that which you have put there, like a string in a maze, so that you shall not lose your way. For existence has its own order and that no man's mind can compass, that mind itself being but a fact among others."
 
House of Leaves by Mark J. Danielewski takes the cake for me. It's a novel written as a first-person narration by someone who finds an academic manuscript about a documentary about a house that measures larger on the inside than on the outside. Only the documentary most certainly doesn't exist. It's a real mind-fuck horror story with a very unreliable narrator. Oh and the author is the brother of the artist Poe, whose album Haunted is sort of the soundtrack for the book.
 
perfume: the story of a murderer by patrick suskind. the whole book was a very uncomfy read, but the ending felt like an assault on my brain. just grotesque.

i'm glad i read it if only so i never have to read it again.
 
An old one and maybe a bit tame by today's standards but 1984 with the rat mask and the ending definitely messed me up the first time.
 
Hands down the most disturbing thing I've ever read is The End of Alice by A.M. Homes. It was one of those reads that let me know that even I, who rarely gets uncomfortable, have lines in the sand.
 
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