Oh... Amber Spyglass. When Lyra and Will agreed to meet on the bench every year at the same time (in different universes), I may have totally lost it.

What Dreams May Come. Amazingly well written, just sad as all hell.

Where the Red Fern Grows brought me to tears when I was nine. Not sure if it's the saddest thing I've ever seen, but I've never cried while reading before or since.

The end of Hamlet is sad, I guess, but it ties the story together so well that it inspires more awe than tears.

Other sad stories include Wit (possibly my favorite play) and Death Be Not Proud. DBNP is just effing depressing. It's awful. If you're tired of having nice days, read Death Be Not Proud and storm clouds will immediately gather above your head.

Asymptote Angel:
Where the Red Fern Grows brought me to tears when I was nine. Not sure if it's the saddest thing I've ever seen, but I've never cried while reading before or since.

The end of Hamlet is sad, I guess, but it ties the story together so well that it inspires more awe than tears.

I agree with both- I've got such a weakness for dogs, and Hamlet is simply amazing......Very sad, but

The book version of Requiem for a Dream by Hubert Selby, Jr. left me emotionally dead for a few hours. It's pretty much exactly what happens in the movie, but reading it makes your imagination imagine so many horrible things.

Ayaan Hirsi Ali's autobiography, Infidel, also upset me, but it was more because I hated knowing that it was all true.

I'll just go ahead and ditto Where the Red Fern Grows. Good God almighty, why would you read that to grade school kids? That's just not fair. I haven't read it since because I'd be a big blubbering mess if I did.

The Sorrow:
A Game of Thrones.

I was waiting for someone to bring up A Song of Ice and Fire. But I dunno what's worse, the end of A Game of Thrones when

I definitely second The Road.

There was this book I read called Strange But True that was pretty depressing -

Nobody's mentioned Charlette's Web? Cah mahn!

Forever war was incredibly bleak at one part. It literally represented the end of the universe for the character in a sense, the end of....humanity.

Oh, and the Amber Spyglass is seconded. Really did cut me up, that one.

Doomsday Book.

Every time I read it, I cry like a little girl.

One Hundred Years of Solitude. I can only say one thing; read it.

The Sorrow:
A Game of Thrones.
And Watchmen. I nearly cried when the best character met an explodey end.

I agree with the Watchmen

I cried near the end of Amber Spy Glass when I was a kid. I almost teared up when I reread it resonantly.

Oh "The Road"definitely seconded,.the ending of that surprised me so much even though everyone who was paying attention knew something bad was going to happen to the man .Damn,Damn and Damn again that ending left me messed up.

The Trial, by Franz Kafka.
It'll make you rethink wanting to enter the legal profession.

I also agree that A Song of Ice and Fire (comprising A Game of Thrones, etc.) can be pretty depressing. But the series is so awesome that it's still a very worthwhile read.

Atonment and the Amber Spy Glass

A Boy Named It
Of Mice and Men, (just the ending).

Does the lyrics sheet for "Objects In The Rearview Mirror May Appear Closer Than They Are" count as a book?

Man on Fire. The end of that book is pretty depressing.

Wasn't very depressing, but it kind of made me sad, and I didn't want it to end that way. It was some book series by Lloyd Alexander, about a character named Taran. Basically, he and his girlfriend had a chance to go to a land where they could live for forever, but they stayed in the land where they would die. And pretty much of them left the main character who were big friends with him.

Hmmm...Harry Potter 7. Y'know, how characters start dropping dead left and right. I got teary when a certain elf died and when Harry used the Resurrection Stone to bring back his mom, dad, Sirius and Lupin and they protected him from the Dementors like patronuses.

Also, Halo: First Strike, a prequel to Halo 2. Admiral Whitcomb and Lieutenant Haverson sacrifice themselves to destroy a Covenant battle station so the chief, Cortana, Johnson and the few surviving Spartans can get away.
Whitcomb tells the chief that they are like the men at the Alamo. Fighting against innumerable enemies, yet still making them hurt.

The original Casino Royale novel is an oddball choice I'll post. But I've read a lot of sad books. Things Fall Apart, 1984, Brave New World, Heart of Darkness, The Things They Carried, The Great Gatsby... How come the best books are always sad?!

Darkrai:

The Sorrow:
A Game of Thrones.
And Watchmen. I nearly cried when the best character met an explodey end.

I agree with the Watchmen

Same for me except I thought...

Two books that have made me cry are 1984 (not sure why, I guess I got so attached to Winston Smith and I was sad to see him go in the wy he did, having given in to the machine around him before death. The fact that the death was so peaceful almost made it worse, what with the whole sympathetic euthanasia thing they had going on) and Lords and Ladies by Terry Pratchett. I know it was a comedy but it was just so well written.

Voodoopigs:
But what is the most depressing book you have ever read?

*Depressing* or *sad*? They aren't the same thing, and sadness does not have to depress. The most depressing book I've ever read was probably Heart of Darkness by Joseph Conrad, but the *saddest* was definitely Where The Red Fern Grows by Wilson Rawls.

Considering I don't read a lot of "sad books" I can only think of one.

Ethan Frome.

If you've never read it, well, you really should. Not even a proper novel; only about 100 pages.

tomdavi:
Two books that have made me cry are 1984 (not sure why, I guess I got so attached to Winston Smith and I was sad to see him go in the wy he did, having given in to the machine around him before death. The fact that the death was so peaceful almost made it worse, what with the whole sympathetic euthanasia thing they had going on).

Going to second 1984 as sad as well; poor winston broken physically, mentally and spiritually.

I'm also going to chuck in "Blind Faith" by Ben Elton which is a lot like 1984 only modernised and full of satire. I really sympathised with Trafford even though I saw his downfall a mile off.

well the thing is i've never really finished a book unless it was an assingment for school, so yea.

Boy in the Stripped Pajamas is amazing, its so sad. Flowers in the Attic would be the saddest book i've read

The Bible. I've never read a book with more death and evil than the Bible. I would hate to live in a world where the God of the Old Testament was real.

The ending to the play Oedipus Rex made me quite disturbed to say the least, it made me sad too. Can't imagine a guy doing that... he married and had kids with his own freaking mother. His mother killed herself shortly after relizing that and Oedipus clawed his own eyes out becoming a blind beggar.

"Where the Red Ferns Grow"
The book pulled in with a happy/uplifting bits for 9/10 then Bam! sad city for the last part of the book.

EmileeElectro:
PS I love you and A child name 'it'
Both were extremely sad and left me in tears.

A child named it. I was only about 13 when I read it, and it made me more angry than sad, that something like that could've happened.

Ooh! And 'of mice and men'. I felt so sad when Lenny had to die.

Flowers for Algernon is probably up there.

The Jungle ends on an upbeat note, but DAMN is that book depressing too.