Desperate Journeys, Abandoned Souls by Edward Leslie needs a mention. A collection of real-life survival stories focused on the Age of Discovery. While not all gloom and doom, more often than not things were terrible and miserable for those poor souls. It’s curbed in that the tales act as a gateway for history lessons about the hardships of sailing and exploring, as well as insights to the morality and thinking of the time.
Looks as though I’m a thorough Philistine where ACfL is concerned. I tried it decades ago, with various then associates of mine having raved about it. Got halfway through at most, and then “bailed”. For me, it was depressing and exasperating in equal proportions – my sentiments, “if I want to read about Catholic monasticism in the Dark Ages (which I’m by no means sure I do), I’ll read about that, plain and simple – not in some convoluted and pretentious apocalyptic-future guise.” I feel that there’s a lot in the general speculative-fiction field, which I just don’t “get”.
Jude the Obscure would take it for me. Although anything I’ve read by Hardy (Dinsdale likes Mayor of Casterbridge, I haven’t read it). Hate fucking Thomas Hardy. Hate Edith Wharton. Hate John Steinbeck (my high school was big on the entire Steinbeck oeuvre.)
If one is a “fan” of depressing Holocaust literature, add Maus to your reading list. Cause nothing like cute little mice heading to the ovens. (I actually wouldn’t recommend most of the depressing classics - I would recommend Maus - its worth the pain).
I’ll throw in something new to this list for people interested in entering Winter Solstice with a slit your wrists sort of book - Atwood’s Oryx and Crake makes The Handmaid’s Tale look like a stroll through the park. There is apparently a trilogy, just the first book was disturbing enough for me.
The Memory Palace, by Mira Bartok. I read it in one sitting; I don’t know if I was feeling especially tender-hearted, but her memoir of life with a mentally ill mother who eventually ends up homeless damn near killed me.
And, of course, that great childhood Book of Dog Death, Where the Red Fern Grows. Gak!
Then avoid Tess of the d’Ubervilles at all costs! 
And to add one I thought about of after previous post: Angela’s Ashes. I think it’s a terrific book and I’ve probably read it five times, but it is a killer.
I’ve read Tess twice. It was my most hated piece of literature, and then I decided to put myself through Jude because I heard it was worse. It is.
I had a masochistic tendency in literature for a while. Plus I don’t remember books well, so if I’ve read something, and then have to be able to discuss it intellegently (say for a bookclub, a class, or to support my kids’ in their homework (hello Scarlet Letter and Great Gatsby), I have to read it again, which is how I read Tess twice.
I’ve read The Handmaid’s Tale at least four times - the first time for “fun.” Then for a class, then another class, then for bookclub.
And the Tess film with Natassja Kinski was pretty wrenching, especially knowing what a rapey f**k Klaus Kinski was :mad:
You put it really well: “masochistic tendency in literature.” I gravitate toward dystopic/uber depressing lit when I’m feeling down, which is the exact opposite of what I should be reading.
Oh, Good Lord, how could I forget this one?! What an unrelenting festival of horror! Every time something even slightly good happened, it was “balanced” by a million horrible things (botched vasectomy, anyone?)
you know the funny thing? Steinbeck non fiction is totally different …try travels with charley …
Lots of great entries so far; my submission is Postcards by Annie Proulx. Many of the books mentioned are worth the read due to the high quality of the literature which is often embellished by the heartbreak and bleakness of the subject matter. This novel is just an ongoing grind of the lives of a family and all they meet well-ruined. Loyal Blood indeed…
Great suggestion and still well worth the read. You keep wondering how much more can this poor kid go through? Have you read the 3rd installation of the Border trilogy Cities of the Plain and did Billy’s experience in that novel balance your read of The Crossing at all?
You have got to press on. This is an absolutely brilliant novel and it does get much better. The entire trilogy is a must-read. Let’s face it, post-apocalyptic fiction probably does need some degree of the bleak to be believable, no?
The House of Sand and Fog by Andre Dubus is pretty damned depressing, and so is the film adaptation. Both are excellent, however, in the tradition of Shakespearean tragedy.
*The Way of a Serpent *by Torgny Lindgren. Man, that’s a story of total despair! But it’s a love to read!
I had to check to make sure I hadn’t written that - I also read it this past Christmas and loved it. I would have HATED it at eighteen though. And I made sure it was the only book I had with me, on a trip - that helps me to sit down and work on a difficult novel.
James K Morrow has a bunch of depressing books, but “This Is How the World Ends” is pretty much the most depressing thing I’ve ever read. It’s pretty much summed up in the title.
The Girl on the Train is the most recent depressing novel, I’ve read. I read it after it had been on all the best seller lists and they had already announced the movie was going to be made. There was not one redeeming character in the book. Even the protagonist wasn’t likable. I don’t even care to see the movie.
I have read that book and I spent the next several years erasing it from my memory. That’s the gold standard in Books to Slit Your Wrists By. My roommate keeps a copy on his shelf as a warning to others.
Anyone else ever read “The Man Who Fell in Love with the Moon?” Disturbing and depressing on so many levels - but a beautifully written book.
It was mentioned upthread, but I have to mention it again. ‘Angela’s Ashes’ absolutely broke my heart.