Most depressing book you've read

I'm at a point in my story where my MC must choose to delete a book off of her Kindle-like device (very important scene...one I hope I never have to live in real life). I want to foreshadow that soon she will be leaving behind her depression and isolation. SO, I need her to discard a depressing book (preferably one with an isolated MC). I'm really looking for a book that just leaves you with a sense of utter hopelessness.

So far I'm thinking of The Road, The Bell Jar, The Grapes of Wrath. But I'm starting to feel like these books are too obvious. (Are they? [I feel like being obvious is very difficult to avoid in lit-fic since the readers are so well-read.])

I need your help, lit-fic-ers! What are some of the most depressing books you've read? (Explanations as to why are wholly welcome!)

The Bell Jar was the first one that came into my mind, as well. So it's kinda obvious, but then again a lot of people know the book and can relate?

Eat Pray Love.

-Shem

Gravity's Rainbow, although it's not entirely depressing. A lot of it is quite funny, but a lot is also horrifying: Europe immediately after WWII, ruthless scientists out for more government funding, cruel sexual experiments . . .

2666 by Roberto Bolano would be a good one. It really leaves you with a kind of hopeless feeling, but shouldn't be too obvious to most people.

The Trial...die like a dog...Whewww....
Book is mostly paranoia and bureacracy, so may not fit your MC's depression, but it's depressing alright. :)

I never read it, but some of my friends have. It's called The Pact, written by Jodi Picoult. Basically, it's about a girl who commits suicide, and it details the aftermath of it for her friends and family, and the traumatic emotions and events in her life that contributed to her suicide.

As you can see, it's not the feel-good book of the century. I feel the need to mention that Picoult also wrote My Sister's Keeper. You know, about the girl with cancer and the other one who goes brain dead? Yeah, that one.

It's not exactly depressing as it is horrifying, but Crash is one where by the end you want to find a shower that can wash your soul.

Something Happened was very depressing, especially the end where the something actually happened.

I agree on the Bell Jar.

Another one is "I Know this Much is True" by Wally Lamb. It's completely depressing until the last like 10 pages, and then all of a sudden it's happily ever after.

God, there's a book I read not too long ago where as soon as I finished it I started sobbing uncontrollably. And now I have no idea what it was. Maybe I blocked it out because it was so sad.

"A Separate Peace" is also pretty depressing if you're the type who puts way too much thought into everything that happened in the story (I am). Basically the story of two boys who can't deal with their feelings for each other or their jealousy, so (SPOILER) one of 'em has to die. So twisted and awful and depressing. Fantastic story, though!

Oh, and of course, the king of Isolated and Depressed Main Characters would be Holden Caulfield of the Catcher in the Rye. But maybe that's over-used?

The Great Gatsby.

1984, because Big Brother's victory is so complete. A friend told me that the moment he finished it he yelled and threw the book across the room.

Waiting by Ha Jin, The Handmaid's Tale by Margaret Atwood or The Grass is Singing by Doris Lessing.

The most depressing books I've ever read were all nonfiction: (1) books about the impending ecological disaster that is our planet, such as the massive extinction episode we're in the middle of; (2) books about how everything in our government is decided by lobbyists for corporate interests.

In fact, those sorts of books depress me so much, I don't read them anymore. I've just settled into a more or less paranoid attitude toward the human species in general. My husband accuses me of being a "know nothing."

Strangely enough, my two most depressing books were in the Fantasy genre. As far as Literary Fiction goes though, I'd say Grapes of Wrath and one of my most favorite ones is As I Lay Dying. :)

Never Let Me Go by Kazuo Ishiguro is pretty depressing.

All kidding aside, I thought Melville's Pierre and Faulkner's Wild Palms were miserably depressing books. In both cases, there was just such an inevitable progression toward utter, sickening despair.

And take your pick of any of AM Homes's books.

-Shem

My favorite book for a few years now has a very depressing undertone:

The End of Mr. Y, by Scarlett Thomas.

It's a fascinating read.

Mockingjay by Suzanne Collins.

(Yeah, I know, popular lit. *facepalm*)

And 1984, by George Orwell. That dystopian stuff can really lay it on.

"We the Living" by Ayn Rand. The essential theme is "the fate of the living under the rule of killers." The story takes place during the Russian Revolution: “bitter struggle of the individual against the collective…a picture of what dictatorship does to human beings…What happens to the defiant ones?…What happens to those who succumb?”

When the MC has nothing left but to choose life in the face of crushing oppression, she journeys alone over "endless stretches of snow" in an attempt to escape across the border.