I don't know if I ever cried because of sadness while reading a book or watching a movie, but I think the book that touched me the most emotionally was "The Catcher In The Rye" by J. D. Salinger.
I often cry out of happyness though, especially when watching Disney films. There are two scenes in "Robin Hood" (my favourite Disney movie, btw) where I always have tears in my eyes while watching it, and I also have wet eyes at the end of Disney's version of "A Christmas Carol" by Charles Dickens. I think there are also scenes in other movies like "Lion King" or "Fox and the Hound" which I can't watch without a few tears, but it's too long ago since I last watched those movies to recall exactly.
That's about it... Sounds pretty emo now that I think about it 







