Ok I haven't seen this ones mentioned so... they are not as fucked as the shit some people have posted but they are interesting readings.
The philosophy of redemption by Phillip Mainlander:
At the beginning there was only god, it ocupied everything, everything was within god, god was omnibenevolent, omniscient and all-powerful so he decides to do the smartest and noblest thing everybody should do: Commit suicide.
Then there was light.
-What is time?: The measure we use to quantify the progressive descomposition of god's body
-What is space?: All that once was ocupied by god
-What is life?: The dying cells of god's body and parasites killing each other of the last scraps of food.
-What is the purpose?: To die, everything is fated to die and at some point all that there is will be filled with the holy silence of eternal rest that is called: THE WILL TO DIE!!!



-What should we do??: Promote the advancement of science no matter the cost so we can create a utopia where mankind live lifes full of hedonistic pleasure until they stop reproducing, each generation becoming smaller until the earth is barren of life.
-Brother that is the worst thing I have ever heard, destroying all life on earth so the last generations of people die in the most decadent hedonism, Kill yourself!!!
-OK
There it is, the most depressing system of philosophy ever created, unsurprisingly it was created by a german guy who lived a really shitty life he also hang himself using copies of his book.
It's interesting from the perspective of seeing an obviously insane person creating a "more or less" coherent system of philosophy that wouldn't be out of place from the mouth of a shonen manga villain.
Danzig Baldaev (all of his books)
Gulag archipielago, a day in the life of ivan denisovich and kolyma tales but illustrated with some of the most horrific art I have ever seen. Seriously, the NKVD were doing things like killing old people with public beatings while forcing people to clap their hands (like china's cultural revolution) or gulag camps for kids (slave sweatshops in all but name and with even more beatings). There is also a book detailing the intricacies (and believe me russian mafia and adjacents loves their complexity even more than alcohol) of russian mafia culture how it was born out of the gulags and what those weird tattoos they wear really mean.
Fun fact, at some point some russian gangsters trapped in concentration camps decided to ally themselves with the regime in order to keep tabs on normal prisioners (some of them were trapped for saying too loud that they were starving) and serving on the soviet army (that was the origin of dedvoschina or brutal ritual abuse that has been carried on since then). Their partners saw that as treason (unbelievable a criminal having no honor) and there was a brutal war between two factions of the russian mafia: The bitch war (suka war).
Foucault's pendulum (umberto eco)
I don't really know if I should put it here. I finished it alongside name of the rose six months ago and believe me brother if I tell you that it manages to surpass even the /x/ section on 4chan.
A team of three /lit/ /his/ posters are bored, frustrated by their autism and forced to work in a shitty publisher house editing grammar errors (like this post) in books written by retards that believe themselves to have talent and pay for their "masterpieces" to be shown to the world. (like amazon publishing but before the internet or something)
The most popular genre of retarded books are conspiracy theories, our guys decide to create the best conspiracy theory book ever written by mixing things based on their knoledge of ancient history, weird philosophical/theological systems, other conspiracies and their god guided reddit reasoning abilities of searching logical inconsistencies in a fictional tale.
They end up creating a cult and the three of them die.
Why is it here??
- For starters our guys are: a turbo neet autist obsessed with jewish culture, a failed history phd and a cuck who is a failed writer. All of their interactions are pathetic, they also spends days discussing how to make their conspiracy theory more believable, at some point they say Ford was a jewish-mason in disguise because the ford-t is designed according to kabbalistic designs (i am not making this up).
It is not a fucked up book in the sense of having lots of sex, blood or a really depressing tale, it is just weird (for me at least), there is also the theme of how people can see patterns even in the stupidest things you can imagine and create tales in order to give some sense to their lifes and how that is one of the most human things to do.