I recommend you see part 1 of my Depressing Shit series and read my original disclaimer here; now here's installment 11.
Just a lite version this time, because it's about time and you need to know what to avoid before it's too late.
All the Light In The Sky (haven't seen it, but the description is depressing enough.)
The Wolf of Wall Street (have seen it; depressing as hell.)
"In The Ghetto" by whoever
More depressing stuff: Read Part 2 here.
And here's Part 3.
And Part 4! Are you depressed yet?!
And as always, I welcome your suggestions for More Depressing Shit. Do comment, and I'll include any good suggestions in a future update.