If you’ve got a lot of time on your hands and you’re not fond of a laugh, Charles Palliser’s Quincunx might do it for you. 800 pages of from bad to worse written in Victorian pastiche. It’s a very odd book, brilliantly done, but it’s a seriously depressing read.
Chaim Potek’s My Name is Asher Lev ;j
I Know This Much Is True by Wally Lamb. One of the best books I’ve ever read, but crushingly sad throughout most of it.
Angela’ Ashes
Paul Gallico’s *Jennie * (*The Abandoned * in the US).
I’m a man and I cried.
My two all-time favourites would have to be Watership Down and The Notebook. I know a lot of people think The Notebook is sickly-sweet (especially since the movie), but I read it shortly after my grandmother, a long-suffering Alzheimer’s patient, finally passed away.
That would have to be Emily Bronte’s Wuthering Heights.
Seconded. One of the first “real” books I ever read (years and years ago). Read it out loud to my daughters a few years ago; it was hard to finish while I choked back tears.
If by “sad,” you mean “makes you want to cut your own throat because of the futility of life,” then, yeah, The Stranger is sad.
Lolita. The futility of when Humbert meets Lolita/Dolores again when she has found someone else is one of the few times that a book has actually made me cry (one of the others was the final Floramor scene in Ada, also by Nabokov).
In fact, in Lolita, unlike in Ada, you can’t help but feel extreme sympathy for all the characters (Quilty excepted,) which makes the tragedy even worse.
A Little Princess, by Frances Hodgson Burnett. How I despise the recent movie version for trivializing Sara’s arc. “All girls are princesses,” says the movie Sara – NO! Book Sara: “Whatever comes cannot alter one thing. If I am a princess in rags and tatters, I can be a princess inside.” Then add, “Left just one for herself. And she could have eaten the whole six. I saw it in her eyes,” and the corresponding final scene: “Her name is Anne. She has no other.” And finally, “To be as proud as that would be a cruel thing. So she actually put her pride in her pocket.” Dammit, I’m tearing up right now.
And I’ve mentioned before that I was awash when I finished The Nanny Diaries. And although his TL-191 series is not thoroughly sad, Harry Turtledove is ruthless about killing my favorite characters. I’m only one chapter into The Grapple, but I’ve got the tissue box standing by. And I beg of you, do not tell me anything. I’ll be in the thread when I’ve finished.
Both already mentioned:
1984
A Canticle for Leibowitz
I agree with many already mentioned. Here are some others.
Children’s: The Velveteen Rabbit, Caretakers of Wonder, Hope for the Flowers
Adult’s: The Lovely Bones, Where Late the Sweet Bird Sang, Look Homeward, Angel, The Last Unicorn
An excellent choice.
Have you ever read Betrayals by the same authour? I think it is his best work (besides being a terrific send-up of “theory”).
My own choice would be Wild Animals I Have Known by Earnest Thompson Seaton. The first really popular book of stories about animals from the animal’s point of view by a leading late Victorian-era Canadian naturalist - and each and every story ends with the heart-wrenching death of the animal hero (of course in the case of “Wully”, the cute dog protaganist turns out to be psycopathic! :eek: ).
The saddest short story of all time has to be “Lobo”. The animal hero is the leader of a wolf pack, preying on sheep and cattle. The ranchers try time an again to catch him or trap him, to no avail. Many instances are given of Lobo’s cleverness in avoiding traps and hunters - he seems to delight in making fools of those chasing him, and the bounty on his head grows. Finally, they hire the author to do it. He realizes after many encounters that Lobo is too smart for him, and instead manages to trap and kill his mate, Bianca. He then uses the corpse of Bianca to lay a sent trail, and cuts off Bianca’s paws to make a trail leading to a trap. The heart-broken Lobo follows and falls into this trap, basically because he is blind and stupid with grief (normally he would have easily seen through the ruse); the ranchers then capture him, intending to show him off. But instead, he refuses to eat and dies of a broken heart. As the cowboys toss Lobo’s corpse in a shed with that of Bianca, one remarks “well, you wanted to be together again, and now you are”.
The Sparrow, Mary Doria Russell… I cry every time I read i
Perdido Street Station, The Scar, and Iron Council, by China Mieville
King Lear, Shakespeare’s saddest tragedy, for me anyway
I only read it a year ago or so, but I thought that The Amazing Adventures of Kavalier & Clay was quite sad. Really, really good, but sad.
The books I was going to mention have already been mentioned:
The Velveteen Rabbit, Watership Down, Charlotte’s Web
There’s also a book by Gary Paulsen called Winterkill which is the first book I ever read that made me cry (the three above, I admit, I saw as movies). I actually cannot remember what made me cry when I read it but it was pretty damn sad. One of those things where you’re sad for days afterwards. I read all of Paulsen’s other books, though.
I can’t say I’ve read any adult fiction that made me cry.
Funny thing about Charlotte’s Web - my brother, a tough 29-year-old guy, was appalled at his girlfriend when she sai dshe was going to show the movie to her 2nd grade class. He was like “that’s the saddest movie in the world. She DIES, man!” hehe
Agreed. The only filmed version of** A Little Princess** worth watching isn’t available on DVD. It’s a 1985 made-for-TV special, and it’s fantastic. I still have the now-21 year old videotape I taped off the television, and I only allow myself to watch it once a year, as it’s starting to degrade. 
I agree with so many of the books in this thread, I’m having trouble thinking of my own. The Giver, I think I’d add to the list. The Kite Runner, certainly.
Zsofia, check out No More Dead Dogs. Funny book, and it may cure you of your Red Fern induced PTSD. 
Oh, man. That book hit me hard, partly because I wasn’t expecting it to be sad, I thought is was going to be a snarky, tell-all bitchfest. The ending almost made me throw the book I was so upset by it. Actually it almost made me more angry than sad.
I’ll also second whoever mentioned “I Know This Much Is True” I am in the middle of that book right now and I am having a hard time with it. It’s too good to put down though, I am in the middle of the Sicilian dad’s memoirs and it is like a whole other novel inside the book. Very good.
I’ll also suggest one no one’s mentioned yet, “The House of Sand and Fog.” Also one of the few instances where I like the movie as much as the book.
“Fall On Your Knees” by Ann-Marie MacDonald was a good one too.