Radclyffe Hall’s The Well of Loneliness has a terribly sad ending.
Bastard Out of Carolina by Dorothy Allison is the saddest book I’ve ever read.
Ghost Children by Sue Townsend. The same person who wrote the funny Adrian Mole books and the hilarious and irreverent The Queen & I also wrote this heartbreaking book about a couple of people after their world has been ripped apart by sad events.
Gain by Richard Powers. Two interconnected stories which portray the arc of a corporation’s life juxtaposed with the story of a middle-aged woman’s fight with cancer. A beautiful book.
A Scanner Darkly by Philip K. Dick.
Sutree and Blood Meridian both by Cormac McCarthy.
All three have a mood of sadness and gloom hanging over every page.
The Sound and the Fury. Geez. It’s depressing as hell.
You know that one part in Benji’s section when he’s at the fence, near the pasture that used to be his, and he keeps hearing one of the golfer’s yell out, “Caddy!”? Man, that was funny at first, but then ten minutes later I was sobbing over how depressing that is. I mean, that’s the saddest thing I’ve ever read; it just killed me.
Speaking of Irving, I always sniffle through the end of “A Prayer for Owen Meany.”
I love books and movies that make me cry.
Thomas M. Disch, On Wings of Song.
The search for complete bliss, and the consequences of the search. Really sad.
I think few books have devestated me as much as Something Happened by Joseph Heller (although I was rather young and impressionable at the time)
Um, can I slip in here with a romance novel? The saddest book I remember reading is called Remembrance by Jude Devereaux. I was so happy/sad for several days after reading it the first time.
Romance novels? Whitney My Love by Judith Mcnaught, it’s a box of tissue kinda book.
I don’t know how many people will agree with me, but I believe that The Lord of the Rings by Tolkien is just about as sad as they come. Tolkien said that he wrote it as a tragedy, and it’s a damn good one. I can’t stand the ending chapter and particularly the last sentence; it always makes me depressed for days on end. It would have been even sadder for me had I not first read it when I was eleven, because I didn’t understand what was really going on and there’s something about reading a book a second or third time that just makes it lose its original power. Just my humble opinion.
War Story by Derek Robinson. Beautifully sad, especially at the end. Makes me want to laugh, cry and grin all at the same time.
For lighter reading, a sad one is Message in a Bottle by Nicolas Sparks. Maybe it was just my mood when I read it but the sad ending really caught me off guard. I don’t really like sad books and movies. There’s enough tragedy in the world to suit me without reading about it too.
Can’t remember the author, but the book was called “Letter to a Child Unborn”. It’s a monologue by a (hopefully ficticious?) pregnant woman who lives in a dictatorship which, for one reason or another, is forcing her to have an abortion. The book is her letter to her unborn child, and is full of all the rationalizations and justifications she can come up with for why the child is better off not being born. Profoundly sad and depressing, particularly if you are expecting or have a child. I know that the author was european and not american.