Where to begin...
Silent Hill 2. God that game is bleak and dark. I don't think I really need to go into too much detail about it here, since most of you already know it. But I loved that game, still in my top 10 for sure.
The Long Walk, by Stephen King. That was a bleak book. It's about teenage boys who have to walk without pause. The worst part is that it's a competition, a race type of thing, and there are people cheering it on and loving it. It's horrifying.
Carrie, also by Stephen King. Be ready for a lot of Stephen King. This book is very bleak, and I absolutely adore it, one of my favourite books. Nothing really happy happens in this books. It gives you some hope, but you know that's redundant because you know the outcome of the book from the start. It's written in such a great way, I do think he got the writing style from Bram Stoker's Dracula, which is written in the same fashion.
Fallout 3. Well, it's a world that's been torn apart and torn even more by nuclear war. It's incredibly bleak, from the setting, to the characters, the way they live.
Memories of Matsuko, a film. One of the greatest films I have ever seen. Go watch it. Go now. It's the first film that's left me sitting there stunned for a good 10 - 20 minutes after just from how good it was. It's very bleak, despite how bright and colourful the film is.
Breaking Bad. Goddamn that TV show. God damn. Just when I think it couldn't be more bleak it just goes and does more.
Lolita, by Vladimir Nabokov. A book of much controversy, but a very interesting read and one I recommend, but it is very dark.