In a similar vein, I haven’t read “This Is the Way the World Ends” by James K. Morrow in 20 years, but I thought it was pretty depressing (and also funny).
I suppose Ironweed by William Kennedy. Won a Pulitzer and all, but what a stone cold bummer.
Angela’s Ashes, for sure. I have read it three times and love it though. More depressing is the sequel, 'Tis. I am reading that right now. Where the Red Fern Grows is another favorite which I re-read recently.
A Child Called It by Dave Pelzer. As a child Pelzer suffered severe abuse at the hands of his mother. When he was finally removed from the home, authorities said it was the third worst case of documented child abuse in the state of CA. To this day it makes me shudder to think about the horrific things his mother put him through.
1984, Lord of the Flies, All the King’s Men, Fail-Safe.
If we’re counting short stories, I’d definitely nominate Annie Proulx’s “Brokeback Mountain”. Beautifully written and poignant but very sad.
I haven’t read the whole of Ian McEwan’s novella On Chesil Beach, but the first part of it was published as a short story that I think would also qualify for depressing-but-excellent.
The recent thread on the upcoming movie version of Fitzgerald’s The Great Gatsby reminded me what a hell of a great book and also what a hell of a major downer it is.
The short story Nightmare in Blue, by Fredric Brown.
Johnny Got His Gun
The Road for me too. It is possibly the only book that made me tear up.
Before My Helpless Sight: Suffering, Dying and Military Medicine on the Western Front, 1914-1918.
This is an excellent book, but it’s also only book I’ve started on the First World War that I could not finish. Relentlessly, horrifically depressing.
What I find interesting about this one is that although the premise is bleak - I don’t think I am spoiling anything to say it is set in the Southern Hemisphere, after nuclear war has destroyed the Northern Hemisphere and the folks in the South are waiting for the toxic radiation to blow down and render the rest of the world uninhabitable - but I found a statement about human dignity and making your own peace with yourself and your situation within the story. So as a literal plot, it is bleak, but as a backdrop to comment on the human condition, it has a somewhat different message.
Again, this is based on a read of it maybe 10 - 15 years ago…
“Night” by Elie Wiesel. It’s not just the whole Holacaust horror - it’s seeing someone lose their faith in God, & me having no answer at all for that. so depressing.
and the last lines of that book just haunt me.
Most of Crime and Punishment was really great but really hard to get through because it was so depressing (until the very end). It was affecting my real-world moods.
A Canticle for Leibowitz is right up there…
I will second Lord of the Flies; I saw the first movie when it came out in 1963 and I was 14, just a bit older than the older boys, so I identified very much with it, and got depressed for weeks. Then I read the book.
And I will third every single Thomas Hardy novel I have read (Jude the Obscure, Tess of the D’urbervilles, and one other that I forget) as being unrelentingly depressing. What was wrong with that guy?
Roddy
The Doomsday Book by Connie Willis. I had read To Say Nothing of the Dog by the same author, which is light-hearted and funny, so I was surprised that the other book, even though it is set in the same universe is…not.
Conspiracy of Fools by Kurt Eichenwald. Because it all really happened.
Ditto. Except now it’s non-fiction.
Year of Wonders. Read it on a plane, cried the whole time. People around me must have thought I was insane.
Connie Willis can do light, quirky humor very well. She also can do depressing, horrible well-written stories, too. I never quite know what to expect when I pick up something by her. (I put off reading Bellwether for years, because I was afraid she was going to be going with the Judas Goat definition of the term.)
The most depressing book I ever read was Rebecca West’s Black Lamb and Grey Falcon. Ostensibly one of the great travel books of all time, it’s also a capsule look at Europe, and the Balkans, just before WWII.
West went to Yugoslavia in 1937, and then wrote of her experiences after falling in love with the people, the land, and even the nation. She detailed little sparks of oral history that she got through her journey, vividly described the architecture that she saw through her travels, and the geography. She often goes on to diversions about Balkan history, from Diocletian, to the battle of Kossovo, and beyond. Balkan history is not often a pleasant thing to contemplate, and she describes it with heartbreaking simplicity. In the background of all this, is the rising spectre of war with Germany, the uncertainty of it, both for West, her home, and for Yugoslavia, itself.
To add to the fun, I picked up the book while I was in the military. In 1991, as the former Yugoslavia was falling apart into another iteration of the racial and ethnic violence that so often comes to that peninsula. When the Serbian forces made news for destroying famous mosques, or bridges, or other architectural treasures, I would know their glory, without ever having seen them, because West had made them vivid in my mind with her prose.
A beautiful, beautiful book, published in 1941 - when things were looking near to their darkest in the days of WWII. The oppressive sense of doom pervading the work was inescapable.