Hmmm, what indeed? Hmmmm....
Ah yeah. Drakengard. Even though I haven't played the game, I have seen all the endings and read a plot synopsis. Not a single ending is actually a happy one. The most shocking one has to be the "final" ending, i.e. the one you get for collecting all the weapons in the game.
But! As far as games I have played, I felt very very miserable at Zack Fair's life from Crisis Core. Was that guy full of misfortune or what? I mean hell:
His mentor Angeal betrays him and then Zack is forced to kill him. Then Sephiroth also betrays him, and as if that wasn't enough, even Shinra betrays him by making him a test subject for four years! While he has a relationship with Aerith! Then, when he escapes he is being hunted by the entire Shinra army. When they finally manage to get him, he is penetrated by a gazillion bullets before he dies. And then that prick Cloud gets not only his sword, but also his identity. And to add insult to the injury when Aerith and Cloud meet Zack's Parents at Gongaga, Aerith tells Cloud that Zack probably forgot about her because he was a playboy. Poor Zack.
And another personal favourite:
Final Fantasy V. When Galuf dies. Yeah, yeah I know, we all saw that coming. This doesn't change the fact that he was the only one who could break free from the crystal that Exdeath was using and kick Exdeath's ass even though he run out of hp!
And a final one:
One of the endings of Planescape: Torment. After absorbing your, let's say, other self and become a mortal man, you bring your companions back to life and wave them goodbye one by one as you teleport to another realm. A realm full of fiends battling each other for eternity. You pick up a mace and start walking towards the conflict which is hinting towards your eventual death. Very downer ending. I remember being very disappointed when I first saw it 10 years ago. On reflection though, perhaps Nameless One can finally rest in peace.
When Eli was killed right in front of Gordon and Alyx by the Adviser, unable to do anything about it. It gets sadder when Gordon & Alyx are finally released and she's just sobbing over Eli's dead body. (I was really moved by this one and found myself swearing to avenge Eli's death.)
When Lord Lucian goes to shoot you, your dog leaps up and takes the bullet for you, thus killing him and you can't do anything about it. (until you either choose the needs of the few or get the Knothole Island DLC.)
At the end, you're incapacitated by a oil tanker explosion, are are the rest of your teammates (excluding Griggs). Griggs tries to pull you to better cover but gets gets shot in the neck while trying to do so. You can only watch as Zakhaev and his men execute your teammates one by one. Zakhaev makes he way to you but is distracted by Russian Loyalists forces that just arrived. A heavily wounded Captain Price slides you his pistol, allowing you to kill Zakhaev and his bodyguards. Sergeant Kamarov reaches you and manages to get you airlifted to safety. Shortly before whiting out, you see a Russian Loyalist medic desperately trying to resuscitate Captain Price...
Oh, let me think...
...
Yeah, I can't think of anything right now, which is odd when you look at the amount of games I've played. I must've felt sad over at least one of them... I've got a vague memory of feeling sad over Kingdom Hearts, but I've no idea of why.
My Sadest moment in Gaming has to be... in Saints Row 2 when you finish a brotherhood mission(rival gang) where you have to chase a truck that is dragging one of your friends along the floor only to finally stop the truck to find that your friend is scared and his body is completly wrecked all over and you cant untie him from the truck, you grab his hand, and while you look over him in the rain, he begins to weep... then you pull your hand gun out and put him out of his missery...
[spoiler/]In MGS4 when you think Snake shoots himself[/spoiler]
[spoiler/]Also in MGS4 when Otacon sees Naomi's last message to him[/spoiler]
[spoiler/]When EE dies in MGS2[/spoiler]
The end of MGS3
Even though it wasn't my favorite, the ending of Twilight Princess
The ending of Kingdom Hearts 1. And when Riku is possessed by Ansem. And...actually, that whole series was pretty depressing.
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