- One Day in the Life of Ivan Denisovich* by Solzhenitsyn
Things Fall Apart by Achebe
The Turner Diaries by Pierce
Michel Houellebecq’s Les Particules Élémentaires (Atomised) is a very bleak (but not moralizing) look at the consequences of 1960s free love and sexual liberation.
The whole book is pretty much relentlessly depressing but there’s one scene in particular that really got me. One of the character commits suicide with sleeping pills. She crushes them in a bowl with her name on it, that she received when she was a little girl. That contrast between the bowl, representing all the joys and hopes of childhood and its ultimate use some thirty years later pretty much crushed me.
If you like McCarthy but want a protagonist who “kept making things worse and worse and worse not because he’s an evil man, but because he’s weak”, try “The Crossing”. It’s about a teenage boy who captures a wolf that has been attaching the family’s cattle and, rather than kill it, he decides to return it to the mountains of Mexico. Things do not go well:[spoiler]Eventually he gets the wolf killed.
And his family (except his younger brother) killed.
And his brother shot.
And his brother’s remains (the brother having been shot again) desecrated.
And his horse stabbed.
And it’s all his fault.[/spoiler]
I think what stands out for me, amongst novels I’ve read most of, is a notable lack of successful lightheartedness. I count two actually funny scenes in the whole book: Eschaton, and one of the torture scenes. Most of the rest of the attempts were either too long-winded or simply rehashing urban legends. Then again, it is more lighthearted than The Scarlet Letter which I was assigned in school but never did manage to read more than a couple chapters of.
Why did I keep reading halfway through? Because it seemed so painstakingly crafted that it might get better. It didn’t. I quit after one of the innumerable lovingly-described death scenes which still managed to not make me care for the dying. I skipped ahead and found a death scene that I did care somewhat about, and it turns out I had missed some context and the guy wasn’t really dying.
I’m torn between Edith Wharton and Hardy. Both have a general theme of their characters bringing misery/tragedy on themselves by being too scrupulous when it does the least good: if Jude and Sue had just let people think they were married, if Tess hadn’t told Angel Clare what had happened to her, if Lily Bart had used those incriminating love letters, if Newland Archer had broken his engagement…
In the end I have to go with Wharton since Hardy often gives me the impression that he’s piling it on. My reaction when I first read Jude the Obscure and got to the part with the kids was “Oh, come on!” Ethan Frome, on the other hand, genuinely horrified me.
I haven’t read a lot of the books mentioned here, though I do remember some of the Steinbeck books from school. The most depressing novel I’ve ever read is All Quiet on the Western Front, a good book, but man I cried reading it a time or two, and that was just a couple of years ago.
Me and a good friend have developed a genre called “books to slit your wrists by.” The most recent one I’ve read was Alison Bechdel’s Fun Home. After I finished that I started looking for my own bread truck to wander out in front of.
Yep. When I first read it in the late cretaceous, it was paired with Rage. He still writes a book every now and then as Bachman.
And speaking of Bradbury, There Will Come Soft Rains, while fascinating, is quite the bummer.
Yes! I discovered To Say Nothing of the Dog about 3 years ago, and absolutely loved it. Hilarious and clever. Plus I’m a sucker for time travel.
I’m still keeping my eye out for the Bishop’s Birdstump…
Yes indeed. If we’re going to get down to short stories, I have a list, and several of them are Bradbury. Soft Rains is one; the other of that scale is the one about the girl on Venus who dreams of the sun, and ends up locked in a closet during the half-hour the sun shines each four years.
All Summer in a Day. We covered that one upthread.
Most of my picks have already been noted but here goes:
Wuthering Heights_“Oh, Heathcliff”…“Oh,Catherine”…Oh, kill me now! I had to read this dreck in high school and it left me permanently leery of anything written by the Bronte sisters.
The Road- This is probably the no.1 most depressing book I’ve read.
1984 - No.2
Dr.Rat- William Kotzwinkle’s dystopian animal tale. I read this when I was a teenager and it really opened my eyes about just how nasty the world really can be more than just about any other novel I’ve read.
That’s the afore-mentioned “All Summer in a Day”. Aside, I originally got my copy of The Martian Chronicles as a prize for a middle-school essay contest based on “All Summer in a Day”.
And I won’t deny that Bradbury is an extremely talented writer. He’s just an extremely talented writer that I mostly can’t read because he’s just too damned depressing.
Fahrenheit 451, though, is an exception. Yeah, it’s bleak, but there’s a ray of hope through it as the protagonist realizes just how bleak it is and decides to be one of the handful to try to change things. Bleak with a ray of hope, I can handle.
TL;DR… I was locked in the closet for a bit. 
Yeah, that one is a real downer. The movie version sent me into an emotional tailspin and for years afterwards I couldn’t hear “Waltzing Matilda” without a sad shiver running down my spine.
The worst part of the story is that it still might come true.
One summer in high school I was assigned On the Beach and Death be not Proud (a 1940s era memoir about a man whose teenage son dies of a brain tumor) for summer reading. They were not fun, frolicky beach reads.
Had to read that one in college. Same month I had to read Sanctuary. So that was a lovely month, filled with fun and cheer…
For me, anything by Cioran takes the cake. Not only are his books endlessly bleak, but at no point is he not absolutely right, or at least convincing, about it 
A bit of a detour here, but I had no idea Death Be not Proud was a book, much less one from the '40s. I only remember the gut wrenching, sob inducing movie starring Robby Benson. Sweet Jeebus, *I *was a “crybaby boobie” after watching that one :o I shudder to think of reading the book.
I’m surprised nobody’s mentioned anything from the Game of Thrones series. I only read the first part of one book, but just based on what I’ve heard it sounds like it’s full of torture/rape/misery porn.
Not mentioned yet:
Harold Frederic’s The Damnation of Theron Ware (1896)
John Edward Williams’s Stoner (1965)
Two American novels featuring nonentity protagonists with aspirations, not to greatness, but to stop being nonentities. Ware is a clergyman; Stoner an academic. Both end up as sad failures.
Not “Tragic” failures, just unrespected and…sad.