Baldur's Gate/Tear Jerker

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• Yoshimo's death. The fact that he's the only proper thief in the game is also sad.
• Jon Irenicus's speech to Ellesime at the Tree of Life helped to humanise and add tragedy to a character who up until that point had been an unrepentant, sadistic Magnificent Bastard.

I... I do not remember your love, Ellesime. I have tried to. I have tried to recreate it, to spark it anew in my memory. But it is gone... a hollow, dead thing. For years, I clung to the memory of it. Then the memory of the memory. And then nothing. The Seldarine took that from me, too. I look upon you and I feel nothing. I remember nothing but you turning your back on me, along with all the others. Once my thirst for power was everything. And now I hunger only for revenge. And... I... Will... HAVE IT!!

• At the end of Throne of Bhaal, if you're in a relationship with Jaheira, her reaction to whichever decision you make is worthy of the name Tear Jerker.
• This troper considers the ending Where Are They Now stories for party members quite Tear Jerker-y. At least, Minsc's "they're together still, up among the stars where hamsters are giants and men become legend." Viconia's romanced non-ascension ending where her past finally catches up with her and she is denied even the experience of seeing her son grow up by the ever-scheming Lolth and her followers is also liable to make your eyes water.
  • This troper has played quite a few mod romances to that stage, and Kelsey's makes her tear up every time. Not helped by the almost sobbing of the voice actor.
    • Kelsey. Tree Of Life. "So let me just say this. I love you. I need you. And I am with you until the end." It's voiced. Cue waterworks!
• In the Tales of the Sword Coast expansion for the original game, the resolution of the Werewolf Island subquest is rather tragic. There is one particular character -- the friendliest one in the village and pretty much the only one who doesn't hold your outsider status against you -- who you can do favors for such as retrieving a cloak and delivering him/her (depending on your player character's gender) flowers. If you pick the nicer dialogue options, the journal entries reveal that you are becoming increasingly fond of him/her. If you offer to take him/her with you to the mainland to start a new life together, he/she will consider it but ultimately refuse out of fear and lingering attachment to the village. That's sad enough. After The Reveal that the villagers are all dangerous werewolves, he/she helps you to evade them and shows you an escape route. Your new friend and nascent Love Interest still refuses to leave and decides to fight the other villagers to buy time for you... and it's heavily implied he/she doesn't survive. The journal entry covering this ends with the words "...I wish...".
  • There is, however, a mod in the works which will allow said villager to join your party in the second game (and even become a full fledged Love Interest). So a nice Fan Retcon on what would otherwise have been quite a Downer Ending.
• Brage, former captain of the Amnish guard and an all around decent guy—until he obtains a cursed sword of berserking. The curse drives him to kill his entire family, a merchant caravan (both people and horses), and who knows how many other people in between by the time you catch up to him. If you choose to return him to the Temple of Helm, Brage will be horrified by what he's done (even though he couldn't control it) and say that he no longer wants to live. Nalin, the priest, instead insists he atone for it all.
• Viconia's ending if romanced. It's such a downer that the above-mentioned Edwin romance mod comes with a happier ending for a romanced Viconia thrown in, though it only triggers if the player "redeems her" and causes her to shift to True Neutral.
• Rasaad's endings; all three. No matter what comes, he dies in ignominy, whatever happiness he enjoyed ending with a miserable death. And no matter what happens, Alorgoth gets off scot-free, the vengeance that defined and shaped Rasaad's Character Development left unfulfilled.
• Durlag's Tower... just the backstory of Durlag's Tower. A dwarven hero builds this home for treasures and family in the late days of his adventures, and then it gets infiltrated by Doppelgangers whom systematically murder his entire clan until only he remains. Then Durlag goes made after slaughtering them because they still wore his family's faces!