Dark Souls/Tear Jerker

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• Every single line spoken by the Daughter of Chaos is absolutely heart-rending.

Quelaag? Please, sister, do not cry. I'm happy, truly. I have you, don't I?

• Solaire becoming possessed is bad enough, but is made undeniably worse by the fact that he's become delusional and believes that he's managed to finally find his own personal sun...
• If the player kill the Giant Blacksmith, his final words are "Nighty-night...".
• Killing Dusk of Oolacile also prompts a heartbreaking line:

Farewell... my rescuer...

• Likewise, Siegmeyer's dying words (should the player opt to kill him) have him calling for his daughter. Try not to feel terrible about that.
• The conclusion to the Siegmeyer and Sieglinde sidequest. When the former goes Hollow, the latter is forced to kill him. Siegmeyer is already dead by the time the player reaches them, with a grief-stricken Sieglinde standing over her father's corpse.
  • An alternate conclusion to the sidequest is no happier. Should Siegmeyer take too much damage during the fight with the Chaos Eaters in Lost Izalith, and survives the fight, he will die from his injuries. To make matters worse, he dies utterly miserable that he's "failed" the player character and his last words have him calling for his daughter, similar to if the player kills him.
• There's a very subtle one involving Witch Beatrice. So you beat the Four Kings, quite possibly with the help of phantom Beatrice, and you're exulting and also wondering just when you're going to meet Beatrice for real, since she's helped you out via phantom sign twice now. And then you go beyond the Kings, and you see... a body with all of Beatrice's stuff on it. The item descriptions make it clear Beatrice lived centuries before you did and could help you due to Lordran's convoluted flow of time, but for your purposes, she's dead. She may have even tried challenging the Kings again after helping you.
• When you get Great Gray Wolf Sif's HP down far enough, he actually starts limping and his attacks become slower. Given that he's a Punch Clock Villain at worst and one of the most beautifully animated creatures in the game, it's hard to score the final blow. Is it any wonder there are so many rumors stating you can spare him at this stage?
• Ceaseless Discharge seems like a one-off, gruesome monster that plays no point but to guard Lost Izalith and a decent armor set, set? Well, according to some hints in game and also outright stated in an interview with one of the creators CD there is actually a brother of the Sisters of Chaos, who was born covered in sores that constantly poured out lava. The Witch of Izalith and her daughters made the Orange Charred Ring to help him with the pain, but he dropped it and the ring was taken by the Centipede Demon. In the interview the director stated that now he's become a sad, twisted giant who's only form of solace is watching over his sisters grave and ignoring the pain from his the lava ceaselessly discharging from his warped body Bet you feel bad for chuckling at his name now, huh?
• Logan's fate if you buy all his spells he will continue his research for what made Seath immortal. After defeating Seath and going back to Logan, he has gone completly mad from the research and disappears the next time you rezone. Upon going back to where you first fought Seath, you can find a now violently insane Logan with nothing on besides his signature hat.
• Several characters you speak to tend to finish conversations with something to the tune of "don't go Hollow". Just a farewell at first, until several of them start Hollowing one by one. How many of their friends did they lose?
• Crossbreed Priscilla. Particularly, killing Crossbreed Priscilla. She's pretty much the only boss that rather than preemptively striking, politely asks you to leave her alone- even Sif just attacks on sight.
  • Even better: When you go into the Painted World and read up on the lore about a "life stealing abomination", you go in expecting to face a horrible monster that was once one of the greatest enemies of the gods. What you find instead is a depressed, lonely, and terrified young woman whose only "crime" was being born a half-breed, and practically begs you to just go away and leave her alone.
• The final section of the game deserves a slot here as well. You spend the entire game working up to this moment, ringing the Bells of Awakening, braving the notorious Sens Fortress, traversing the abandoned streets of Anor Londo, and overcoming all other obstacles to open up your final destination. What awaits you here? The Kiln of the First Flame. A wasteland desert made of ashes and partially melted architecture, completely quiet and devoid of life other than the few remaining Black Knights guarding the final area Dispatching these final enemies what is there as the final fight in this game? None other than Gwyn, Lord of Sunlight. Now reduced to the Lord of Cinder, having been BURNING in the Kiln ever since he first lit the First Flame. And to make matters worse? He gets no intro cinematic, no dialogue, you just have this once great man lunge at you as soon as you cross the fog, as a simple, elegant, and impossibly depressing piano piece plays as you fight this fallen hero. Both to accomplish your goals, and for this point it'd seem to be put him out of his misery
  • One Youtube comment described it as less an epic boss battle and more an execution of a frightened and lonely old man afraid of change.