I'm almost sure that I'm going to be the only one to list this, but Christina's death in Assassin's Creed Brotherhood.
Christina single-handedly switched my view of Ezio from
"Holy shit this dude is awesome! DANANANANANANA RENAISSANCE BATMAN!!!!"
to
"Dude....I'm soooo sorry. Everyone in your life that matters most ends up dying... Everything you love is taken away from you. Your life is nothing but soul-crushing misery and revenge..."
Harry Mason at the beginning of the game, especially when you don't realise just who Heather's dad is. It came as quite a shock to me. I spent so much time with the man in Silent Hill, we went through hell together and all he gets is a lousy murder off screen. I couldn't even do anything to prevent it...
Honourable mentions for the games already covered:
Half Life 2: Episode 2
Eli Vance
The Walking Dead
Carly, Duck and Lee
Metal Gear Solid 3
The Boss
Silent Hill
Lisa Garland
Dreamfall: The Longest Journey
April Ryan..?
Bioshock 2
Augustus Sinclair.
Don't look at me like that! I know the game was awful but I grew quite attached to the man and what Sofia Lamb did to him was quite horrible.
Crono is your big man who is Luminaring stuff like a boss then you get up to Lavos in a tense scene and... there he goes. And the way he goes. The giant Lavos laser. FMV from the PS1 version is key for this. Also, Janus warning of the death is even sadder.
Then, there is Magus in the non-canon ending. When you meet him at the Northern Cove after the Blackbird, you can either have Frog decide not to fight because it is not worth it or you can fight him with just Frog. Even when you beat him, he is willing to help you save Crono.
This might be an odd one but Fallout 3
And this is common knowledge to a lot of people but
Your Dad dies and Liberty Prime
The thing that makes this sad, for me anyway, is just the utter helplessness of it. You go around attempting to save him and in the end, NOTHING, NOTHING can save him, you just have to watch.
And the other one because he's such badass and he just dies in a "WTF just happened" moment where you are left dumbfounded.
I would have to say Lavitz from Legend of Dragoon.
He showed what a true knight is by bravely sacrificing himself to protect his king and friend. Also, he seemed like an older brother to Dart. Not only that, he was a pretty likeable character and eerily relatable to real-life death.
Final Fantasy Crystal Chronicles: Rings of Fate. Not 100% why it affected me so much when I got to it but man, when
Chelinka
died I couldn't help but cry. Maybe it's because it was just a different sort of tone than I was used to because even after I saved the world, everything was happy for everybody except the main character, and then that happens on top of that.
Lugo's lynching by the refugees. It was just so sudden and brutal, and the entire atmosphere while Walker and Adams tried to save him while a group of refugees tried to attack them. And nobody in that game ever dies cleanly, they have to die by rotting or being beaten apart.
I'd definitely say Roland's death in Borderlands 2 was the saddest for me. I really liked him in the first game(I played as him) and in the second game as they made him a really cool character.
The saddest death for me would probably be in Sonic 2006. Holy hell. The death of Sonic there was just so moving.... it was probably the first time in my life I ever cried....
*ahem*
All sarcasm aside...
Honestly, the saddest death I can recall would be from Borderlands 2:
GODDAMMIT JACK, why'd you have to kill Bloodwing? Mordecai was my guy in BL1, and Bloodwing was so badass. It's compounded by the fact that I saw it coming from the start of that fight, the whole "I forgot one... hm...." thing, but I couldn't stop it. At all. Whenever I started to feel ANY remorse for Jack, I instantly remembered Bloodwing and got in such a goddamn rage it's not even funny.
As an aside, I never really understood the depression caused by Aeris' death. Most of the characters in battle seemed fairly generic at the time (aside from limit breaks), so the loss of a battle companion wasn't too upsetting, and she never seemed so much of a character as a likable plot-device. From what I've ever seen, unless you take the romance with her, she never evolves past the whole "last of her kind" thing, and that only gets you so far; I can't really relate with one-dimensional characters that well. Not to mention the whole "you kill her yourself" thing was horribly executed (was bad here, was bad in AC:B. Honestly, while usually I'd rather do things myself than see them in cutscenes, this is the one exception).
Find and rescue Sif in the Abyss. Summon his help to fight Manus. Finish DLC. Go back to original timeline.
Fight Sif at Artorias' grave.
Cry.
Cry forever.
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