Sorry there's so many- I went a little overboard...
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In Blood+ (the anime) when...
In Full Metal Alchemist (the anime) when...
In The Green Mile (Wow, going from two animated shows to a novel? What a swap!) when...
In A Game of Thrones (Another great novel that nobody seems to have heard of...) when...
In Silent Hill 2 when...
In Call of Duty 4 (I think it's 4, at least...) when...
And finally, in the Half-Life series when...
Any of the little liberation soldiers that decide to hop on the Freeman bandwagon died. I don't know why, but it really busted me up to see my little squadlings bite the dust- especially when it was my fault as the player. I literally replayed entire sections of levels just to protect them.
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In Blood+ (the anime) when...
Pretty much -all- of the Schiff (or Sif, whatever.) die- except for John. Nobody cared about John; not even me. Even the deaths of the Asian wonder-twins made me more upset. In addition, Solomon dying seemed really pointless, and the way he died pretty much set my piss to a boil.
In Full Metal Alchemist (the anime) when...
Maes Hughes died. I mean, seriously- not only was he the lovable (albeit irritating) family-man, but he got shot and killed by an imitation of his wife. That's just not fair.
In The Green Mile (Wow, going from two animated shows to a novel? What a swap!) when...
John Coffey and Delacroix were executed. As to why their deaths upset me, there just seemed a measure of injustice in both. For John it was obvious- he died for a crime that he did not commit. And with Delacroix, though he probably deserved to die like that, I grew to love him as a character and was very saddened by the whole being... melted thing. (Also, Mr. Jingles the mouse when he got stomped by Percy- but then John brought him back to life, so it was all good.)
In A Game of Thrones (Another great novel that nobody seems to have heard of...) when...
Eddard Stark gets beheaded. And not only was he beheaded by that little Lannister monstrosity, but it was with his own sword. Talk about a bite in the rear.
In Silent Hill 2 when...
James kills himself in the Bad Ending (or the In Water ending, whatever). I knew about that ending and strived like heck not to get it, but I got it anyway- and that coupled with the fact that I adore James Sunderland made it all too bad of a thing.
In Call of Duty 4 (I think it's 4, at least...) when...
Gaz dies. I didn't actually see him die, but after watching my cousin playing and commenting about how much I loved Gaz, he promptly informed me that he gets shot. And damnit, though I didn't know his character for that long, I loved the man.
And finally, in the Half-Life series when...
Any of the little liberation soldiers that decide to hop on the Freeman bandwagon died. I don't know why, but it really busted me up to see my little squadlings bite the dust- especially when it was my fault as the player. I literally replayed entire sections of levels just to protect them.
And also- courtesy of that moron who didn't put Eli Vance's death in spoiler tags- I'm pretty upset over that now, too. I would rather have seen for myself... -is on the last leg of the current Half-Life game and wasn't aware-