For me its definitely Almost everything in Metal Gear Solid 4.

*Spoiler Alert*

IN skyrim in the Dark Brotherhood I escape after poisoning the emperor only to find out that he was a double and the whole thing was set up by someone in the DarkBrotherhood. I quickly return to the sanctuary to find it was being attacked by the emperials. I quickly look for survivors as the whole place was burning down. I pass by a few of my fellow assasins now dead. Eventualy I find Nazir the redgaurd we both work together to find a way out of the burning sanctuary. I heard the Night mother call to me to hide in her casket. I obey and soon I hear everything falling around me and the casket falls into the pond. after awhile Nazir and Babette rescue me and the night mother tells me of a survivor and that I should tell Nazir and Babette. We both search for the survivor only to find Astrid with burns all over her body. It was the most horrible site to see because she should have died with all those burns. Astrid said that she was at fault for the downfall. She only meant to save the Dark Brotherhood and that she was selfish to try and keep control of the sanctuary, but she relized her mistake and said that she agrees that it would be better for there to be the night mother. She then gave me a difficult contract, she said to use her dagger and kill her. I did as she asked, and so I killed her.

IN skyrim in the Dark Brotherhood I escape after poisoning the emperor only to find out that he was a double and the whole thing was set up by someone in the DarkBrotherhood. I quickly return to the sanctuary to find it was being attacked by the emperials. I quickly look for survivors as the whole place was burning down. I pass by a few of my fellow assasins now dead. Eventualy I find Nazir the redgaurd we both work together to find a way out of the burning sanctuary. I heard the Night mother call to me to hide in her casket. I obey and soon I hear everything falling around me and the casket falls into the pond. after awhile Nazir and Babette rescue me and the night mother tells me of a survivor and that I should tell Nazir and Babette. We both search for the survivor only to find Astrid with burns all over her body. It was the most horrible site to see because she should have died with all those burns. Astrid said that she was at fault for the downfall. She only meant to save the Dark Brotherhood and that she was selfish to try and keep control of the sanctuary, but she relized her mistake and said that she agrees that it would be better for there to be the night mother. She then gave me a difficult contract, she said to use her dagger and kill her. I did as she asked, and so I killed her.

Did this recently. Was surprisingly touching, ROFL. Bit said, didn't wanna kill Astrid, tried walking out at first, see if it would save her or something, like leaving her would end the quest to kill her, but in the end I slaughtered her. Poor gal.

You know it wasn't as sad but the ending to Force Unleashed 2 was quite sad but you kind of have to expect it because he had to die for the storyline. But it was like everything he ever cared about was ruined.

The entire god of war series , i know this sounds strange but at the end of gow iii you get this major "wow , did i just find out that i like was used by everynone this entire ****ing time"

@R3LOAD
Yeah you do something very similar to that in Oblivion. In the dark brotherhood but you kill this Khajiit that wants to be friends with you and your like "sorry I have to beat the game-" slice

Spoilers if you haven't beat the quests, so read at your own will and all that jazz.

I would note that some quests/quest lines in Skyrim and Oblivion had their sad moments, but I only saw the members as a means to an end.  While playing the Dark Brotherhood in Oblivion the moment Lucian said I had to Purge the Brotherhood...I muttered "Gladly." In Skyrim I felt satisfaction in seeing Astrid on the floor dieing, and her mouthy husband dead as well.  Killing Cicero made me feel happy.  I'd destroy the Night Mother If I could.  These games dont hold a quest dark enough to satisfy me.

@R3LOAD
Yeah you do something very similar to that in Oblivion. In the dark brotherhood but you kill this Khajiit that wants to be friends with you and your like "sorry I have to beat the game-" slice

Oh yeah, I remember that. I enjoyed killing them all, I liked the Khajiit, though. If only he was out of the sanctuary like the wood elf used to do sometimes, I'd see her around cities sometimes. Wish the Khajiit did that, and it made you just leave him alive.

Oh yeah, I remember that. I enjoyed killing them all, I liked the Khajiit, though. If only he was out of the sanctuary like the wood elf used to do sometimes, I'd see her around cities sometimes. Wish the Khajiit did that, and it made you just leave him alive.

They were all innocent but then again technically speaking none of them were innocent and they were all evil.

skyrim, someone took my sweat roll and i couldn't kill him for it without being killed myself. lol just kidding none of that happened but if it did happen, *sniff*