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Sad/Grim/Dark/"Depressing" Games?

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Such an unsettling game.

whoa, blast from the past!

Surprised no one's mentioned Passage. What a fucking punch to the gut that game is.
 
Came in here to mention I have no mouth and must scream, but a lot of the PC games at the time were really depressing. Alone in the Dark, Phantasmagoria, Gabriel Knight, Myst, 7th Guest, even shooters like DOOM and Heretic. I remember playing one of the earliest polygonal games at the time, but I can't remember its name. It had werewolves, suicides by monks and more depressing shit. It depressed the hell out of me. Those were different times though.
 
Shadow of the Colossus and Braid pop into my head.

Really want to sink my teeth into Spec Ops and Bioshock Infinite after hearing the praise they get.
 
Digital Devil Saga (1+2).

DDS series deserves more love in it being an attempt to be the antithesis of persona games. The characters in these games are just as enigmatic as ones from persona but devoid of all the childishness of the latter, something which I really appreciated. Oh, and the combat was really fun too.

And I should mention that although not "depressing", the stories of Altair and Ezio that spanned AC2: Brotherhood and Revelations were quite a bit melancholic. The way Revelations somberly concluded Altair and Ezio's stories produced a bigger emotional reaction of out me than any twist AC has thrown at me so far. Whoever was responsible for managing characters of Ezio and Altair in AC2 trilogy should have been assigned for managing Desmond's character as well.
 
DDS series deserves more love in it being an attempt to be the antithesis of persona games. The characters in these games are just as enigmatic as ones from persona but devoid of all the childishness of the latter, something which I really appreciated. Oh, and the combat was really fun too.

You haven't played Persona 2: Eternal Punishment, have you?
 
Half Life 2 is pretty grim, when you think about it.

Earlier in its development, Half-Life 2 was much more dark and grim than what we ended up with.

http://combineoverwiki.net/wiki/Development_of_Half-Life_2

...City 17 was an American East Coast-like city based on Washington, D.C., with many huge skyscrapers, and had a very basic, blocky FPS design. It was more faithful to the concept art seen in Raising the Bar: darker, gothic, sinister, rainy, foggy, gritty, with a lot of brick, metal and glass, getting along well with the cut concept of the Combine replacing the air with poisonous gas and draining the oceans. It was therefore a much more dystopian, Orwellian universe (even though the final product is still quite Orwellian) even with touches of cyberpunk/steampunk style, in the vein of the book/film 1984 or other films such as Dark City, City of Lost Children, Avalon or Blade Runner. It was also more faithful to Viktor Antonov's early concept art and work on the game.

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a few depressing/sad ones for me:

bastion
i am alive
braid
limbo
deadlight
god of war (i felt sorry for kratos in the first game)
enslaved
 
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