Once again this really made me thing, and the closest I got was the scene in Castlevania, Lord of Shadows [spoiler alert] where Gabriel while sleeping evidently kills his companion, a mute girl called Claudia. The moment though is short lived as Claudia is accompanied by the Black Knight, who is a giant suit of armour built by her father to protect her. He’s a little bit miffed at what you’ve done to daddies little princess and so the dark revelation quickly transitions from shock and sorrow to a fight for survival. You’re not really left long enough to dwell on what has just happened and feel and real sadness.

Claudia and her guardian, the dark knight

Exploring deeper emotional experiences has been on the radar of game developers for a long time. In the eighties a small start up company posed the question “Can a computer make you cry” which I think was in part an effort to get video games recognition as a more mature medium. After all, the idea of a book or a film that makes you cry is well established and I’m not ashamed to admit that I’ve been prompted to shed the odd tear here and there (LoveFilm once sent us a”Romantic Comedy” starring Kate Hudson called A little bit of heaven. You’ve been warned).

These folks from a start up company called Electronic Arts asked if a computer could make us cry. I wonder what happened to them.

The first serious attempt to invoke sadness in the player that I’m aware of came in 1983 with a game called planetfall. In planetfall you are accompanied by a robot guide. The creators put a great deal of effort into trying to get the player to put some emotional investment into this character, who was to ultimately sacrifices himself so that your avatar can go on.

I think the problem with this approach is that it is primarily story driven. If you want to progress the character must die. This is fine in books, but games are an interactive medium, and there lies the second problem. Good games are made up of meaningful choices. If you are given meaningful choices that make you feel sad, then you have to believe that you could have made better choices, and that feeling isn’t fun. This is in contrast to books or films where there are no choices to make. Also, to keep you playing they are unwilling to punish you too harshly for your mistakes. For example, if Mario mistimes his jump and falls to a fiery death in Bowser’s castle, well, he might be sent back to the last checkpoint, but he lives to fight another day. That raises the question as to whether you can really feel empathy for a character who has limitless lives. A chap called Jason Rohrer made a game called The Passage that attempts to break this cycle. It’s free, and worth considering. I think it say something about life and the futility of material things, but that’s just me.

Another game that isn’t much fun, but is still compelling to continue playing is a game called Dafur is dying. It’s an online game that highlights the plight of refugees in Dafur at the hands of Militia who are backed by the Sudanese government.
You can play Dafur is dying at www.DafurIsDying.com.

Anyway, I’m not really happy with my answer for this question. One aspect of games is that you have to enter into them willingly. If a game is making you sad as a consequence of controllable dynamics and not of a linear story then you’re not likely to keep playing.