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 whenThe Sorrow said:A Game of Thrones.
Eddard Stark is executed
Robb and Catelyn Stark and a bunch of others are slaughtered at the Red Wedding
There are many tragic moments throughout the series, but those are definitely the worst.
I definitely second The Road.
There was this book I read called Strange But True that was pretty depressing -
This young couple get into a car wreck on Prom Night. The guy dies and the girl is horribly disfigured. She ends up living by herself in near poverty. She becomes pregnant and she's convinced that through a miracle her dead boyfriend impregnated her somehow, but it was actually her landlord, who has been slipping her rufies every night and raping her.
The dead guy's brother, meanwhile, is emotionally and verbally abused by his mother, who tells him that "the wrong son died" because he's gay. He leaves home to live by himself in New York city. He invites a guy he meets online over to his apartment, who turns out to be a bigot who was trolling for gay guys online just to harass them. He forces his way into the apartment and abuses the guy and lets loose the bird that belongs to the man who's subletting the apartment to him.
And I think some other pretty bad stuff happens, the guy who's been raping the girl ends up killing his wife for some reason (I think she finds out about the rape).
The dead guy's brother, meanwhile, is emotionally and verbally abused by his mother, who tells him that "the wrong son died" because he's gay. He leaves home to live by himself in New York city. He invites a guy he meets online over to his apartment, who turns out to be a bigot who was trolling for gay guys online just to harass them. He forces his way into the apartment and abuses the guy and lets loose the bird that belongs to the man who's subletting the apartment to him.
And I think some other pretty bad stuff happens, the guy who's been raping the girl ends up killing his wife for some reason (I think she finds out about the rape).