Heavy Rain, pretty much 70% of the game is pure tear jerker material. Watching the kid die, watching Ethan go through the trials, watching literally any of the non "happy ending" endings.
The ending of Red Dead Redemption also made me sad, but in a different way. After my incredible journey with Marston, it was over, and he well paid the price for his past and for his family.
Metal Gear Solid 3 as well. The final boss fight with The Boss, and the twist ending that sends Big Boss over the edge into a jaded man instead of the naive patriot he once was.
Finally, I thought the ending of Call of Duty 4 and the Nuke in the middle were just a tad sad. Not enough to elicit an emotional response, but in both cases you see the devastation of war and wonder "is... is he going to live? Are they ok?" Because you don't expect such drastic losses and moments in a game.
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