1. Guts by Chuck Palahniuk
“A total of 67 people passed out or needed medical assistance when he did a national speaking tour where he read it aloud.” — JellybeanFernandez
2. The Mysterious Stranger by Mark Twain
“It’s the most cynical, pessimistic, ‘darkest’ thing I’ve ever read.
The story is essentially about three Austrian children and their encounters with Satan. Satan attempts to convince the children that God is either nonexistent or indifferent to human suffering, that life is ultimately meaningless, and that humans are doomed, ignorant creatures.
Many scholars believe The Mysterious Stranger expresses Twain’s own despair towards the end of his life.” — MVB1837
3. 120 Days of Sodom by Marquis de Sade
“The word ‘sadism’ is derived from this guy’s name!
It tells the story of four wealthy male libertines who resolve to experience the ultimate sexual gratification in orgies. To do this, they seal themselves away for four months in an inaccessible castle… with a harem of 46 victims, mostly young male and female teenagers, engage in the sexual abuse and torture of the victims, which gradually mounts in intensity and ends in their slaughter.” — snackbot7000
4. The Girl Who Loved Tom Gordon by Stephen King
“It’s one of Stephen King’s lesser known works and it is pretty fucking disturbing. It’s about a nine year old girl who gets lost in the Northeast American wilderness. It’s pretty dark given the fact that it mostly focuses on the girls mental state as hunger, exposure and dehydration cause her to loose touch with reality and go insane as she is faced with death. Also, over the course of the book, there are increasing signs that she is being stalked by a supernatural creature hell bent on killing and eating her. It was quite hard to make it through the whole book.” — quitpayload
5. Blood Meridian by Cormac McCarthy
“Probably the darkest book I’ve ever read, personally. Biblical in prose, disturbingly violent detail, all wrapped up in a nihilistic interpretation of the West. Plus, it has the most unsettling/interesting villain of all time in it. A man who seems to represent the vast sum of human violence, encapsulating both all its knowledge and all its depravity.
Cormac McCarthy may have missed out on being hugged as a child, but he’s an indisputable literary genius.” — Interminable_Turbine
6. Johnny Got His Gun by Dalton Trumbo
“Hopeless from the start, and only goes downhill. You’re stuck with him as a prisoner in his own mind, and you get to bear witness as he goes stark-raving mad.” — tumblechuckles
7. Blindness by Jose Saramago
“Pun intended. It’s a pretty fucked up book though. I think for me the shocking part was how fucked it got. I mean, if you read ‘American Psycho,’ you kind of know what you’re getting into. But in ‘Blindness; as things gradually become worse and worse for the characters it’s like the boiling lobster metaphor, and suddenly it hits you that holy shit… This is really fucked up and humans are basically monsters.” — Shigdig7
8. The Little Girl Who Was Too Fond Of Matches by Gaetan Soucy
“I’m no literary expert, but the book seems kinda normal until you get near the end and then you realize everything you thought you knew was wrong and it’s actually a hundred levels of fucked up.” — hermitsdayout
9. Crossed by Garth Ennis
“Garth Ennis’ Crossed has my vote for ‘darkest comic book’, at least. The antagonists rape/kill a couple and their young daughter when they catch up to them in the first few pages. The husband’s intestines are hanging out while he is being raped, still alive.
That’s how the comic starts. It gets bleaker from there.
It was one of the only two things I’ve ever noped out of finishing reading.” — JDAlvey
10. House of Leaves by Mark Z. Danielewski
“It will make you feel cold and closed off from the world, and alone in a vast universe of darkness and gritty human emotions. It pulls you in slowly, making you experience every emotion the protagonist feels as his fate unfolds in a beautiful literary masterpiece.” — demonchefofportland
11. Living Dead Girl by
“It’s a teen book written from the perspective of a girl who was kidnapped by a pedophile as a child. She has been living with him ever since, but he is no longer as attracted to her since she reached puberty and he is making her help him kidnap her replacement. She knows that he intends to kill her once her replacement is found, and she knows she’s not the first girl he’s kidnapped.” — Elphabeth
12. Lullaby by Chuck Palahniuk
“Lullaby by Chuck Palahniuk (guy who did fight club) is pretty messed up. After a string of misterious infant deaths, a journalist discovers that a poem in a lullabies book is actually a curse that kills whoever the speaker is saying it to to. I don’t want to give too much away, but it’s a story about this guy tracking down all the copies of that book and poem and all the crazy horrible and bizarre things that happen along the way.” — SoWhatComesNext
13. The Painted Bird by Jerzy Kosinski
“Author offed himself after writing it allegedly.” — devoricpiano
14. The Book Thief by Markus Zusak
“This book is set during World War II and the narrator is death, which is an extremely interesting perspective. Its a hauntingly beautiful story and I highly recommend it to everyone.” — penea2
15. Song of Saya by Daniel Liatowitsch and Todd Ocvirk
“It’s a visual novel that’s not terribly well known, but it’s crazy Lovecraftian levels of fucked up.” — Penguin_Out_Of_A_Zoo
16. 1984 by George Orwell
“1984 is the darkest I know of.
Humans have built a society that exists for no purpose but to be a boot grinding the individual into the ground.
If you rebel in the smallest way, you won’t be killed. You will be tortured and tortured and tortured by all you fear most in the world. This will continue until you love your lot in life. You will be tortured into loving all you hate, and hating all that you love. This is inevitable.
And then they kill your body.” — tyguytheshyguy
17. Notes From the Underground by Dostoyevsky
“I’ve never been able to finish Notes From the Underground by Dostoyevsky.
I’ve read so much shit. Barker, King, Brite, Gaiman, filthy love letters by european swingers. Nothing makes me as depressed as Notes From the Underground.” — MidasVirago
18. Heart of Darkness by Joseph Conrad
“It’s ultimately about the darkness at the heart of human existence. The journey into the colonized and exploited jungles of Africa was an incredibly apt and timely parable, rendered with unsparing detail. Kurtz’s madness is inevitable.” — ialsohaveadobro
19. Lolita by Vladimir Nabokov
“What other book makes you nod in agreement with a pedophile child rapist?” — automator3000
20. Gerald’s Game by Stephen King
“I nominate Gerald’s Game by Stephen King due to the graphic incest and the creep factor. There’s a bit about 80 pages in that almost made me crap myself.
And Closing Time by Neil Gaiman. Short story with an unreliable narrator but very dark and creepy. They made it into a short film for Neil Gaiman’s Likely Stories but it needs to be read first.” — howkflakegirl
21. We Need to Talk About Kevin by Lionel Shriver
“It’s about a teenage boy (Ezra Miller) who commits a school massacre and how his mother deals with it afterwards with flashbacks to his childhood and growing up. It’s a really dark story because it has no catharsis or any answers whatsoever and truly is gazing into the abyss.” — Noggin-a-Floggin
22. Metro 2033 by Dmitry Glukhovsky
“This book is amazing until you make the mistake of listening to the audiobook outside in the dark… and then you just want to run as far away as possible.” — Crytetra
23. Berserk by
“I would encourage anyone into medieval fantasy to give berserk a shot. Its is an exceedingly highly acclaimed dark fantasy manga, but relatively unheard of in the west due to the medium.” — ElectricDruid
24. American Psycho by Bret Easton Ellis
“American Psycho, for many reasons, but mainly the child in the zoo chapter.” — regretienne
25. The Wasp Factory by Iain Banks
“Not hugely well known, but also not the darkest book EVER but it is the most beautiful book I’ve read about a child serial killer.
The author’s sci-fi is the tits, though.” — Damnyoureyes
26. The Metamorphosis by Franz Kafka
“The Metamorphosis by Kafka is pretty fucking dark. A man who single handedly supports his family (parents and sister) wakes up one morning as a giant bug. His family gradually comes to resent and despise him now that they have to work to make ends meet and keep him hidden. His father inadvertently injures him and he spends most of the book in utter torment and resolves to die in the end to stop being a burden. In the end, his entire family is relieved he is finally dead basically their lives are great after he’s gone.
Read Kafka if you want to experience true self loathing.” — Mat_the_Duck_Lord
27. Any story written by Harlan Ellison
“So many Harlan Ellison stories would qualify. ‘On the Downhill Side’ is about a unicorn, an actual, honest to god, mythical, beautiful unicorn, being sacrificed to atone for the sexual sins of mankind. It’s one of the most upsetting and depressing stories I’ve ever read. ‘Mefisto in Onyx’ is about a telepath who enters the mind of a serial killer and ends up being possessed by a demon who it turns out was actually at the core of every notorious monster in human history. ‘The Deathbird’ is an indictment of God Himself as a sadistic monster who pinned all the evil in the world on Satan and got away clean. It was inspired by the hateful and unfair death of Ellison’s dog, a story told in painful detail in the story itself. Ellison is VERY, VERY dark, and very good. It bums me out that most people these days only know him for being a litigious and contentious nutjob, if at all, because he’s probably my favorite living writer.” — ArtSchnurple