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Tear Jerker: Marathon
Depending on how sympathetic you are to him, Durandal's death(s) are this. All of them. Especially the one in Marathon 2 where the player himself has to kill him by smashing the computer core that he's running on, telling you to do so in his normal cool, collected manner while literally falling apart. Of course, he gets better. Also, the end of Hang Brain where Durandal is taking himself apart so that he can store some fragment of himself in the Player Character's brain.
