A2R.
Member
You sound like my wife. Our reading tastes are rather different. She usually doesn't trust my recommendations — unless I mention that it's depressing!
Off the top of my head, The Grapes of Wrath, The Jungle, and Bastard Out of Carolina, stand out in my mind as pretty depressing.
The Grapes of Wrath was pretty depressing.
I found The Great Gatsby to be rather depressing as well. Any life lived in vain is.
The beginning of Life of Pi is also a tear-jerker.