Re: Saddest Games
Deadly Premonition made me cry, but more because of the dawning realisation that this AMAZING GAME WITH "CULT HIT" WRITTEN ALL OVER IT, that I had paid around £15 for, was a pile of shit gameplay-wise.
But seriously, not many games come to mind; there certainly hasn't been one that has made me cry. The best I could do is describe games that have made me feel emotional, and still, this would be no easy task. One that does stand out in my head is The Darkness. It has a truly great narrative anyway, but there are a few scenes that are scripted and you have no/ little control over that help it to stick in my mind. The scene involving Jenny's fate fairly early on is wonderfully done.
Also, the end of Red Dead Redemption was pretty powerful for me, for a game that was quite happy to play itself as GTA: Cowboy edition for a large portion of the runtime. The last third of the game, though, (especially John Marston's fate), was wonderfully done, very sombre.
I'd love to hear more examples myself. Good question!