The most sad and depressing moments in gaming

The ending of fear 2

The evil ending for Infamous 2. *sniffles*

Nope. Never really got emotional while playing a game. Well, once, while playing DA2...

Spoilers: When your mother dies, I was bummed out, because the main character had no one else. And that death was pretty damn gruesome. It was a cheap way to squeeze out some emotion from me, so I hate that scene.

So except for that, never. I don't know why, vidja games never made me sad. Movies though, hoooo boy.

Have you played Persona 2?

Nier, the ending. Especially Ending D, which must be one of the most gut-wrenching things throughout every medium.

The FF Tactics ending. Haven't seen that mentioned yet.

It's a cliche, but Aeris in FF7 man.
 
Twenty-plus hours of dedication and suddenly it's 'Goodbye, healer'.
 
Also the proper ending of Lylat Wars (or Starfox 64).

'Don't ever give up, my son'

Never cried for a game, books and films maybe, but not games. But they can still be emotional and sad though. 
 
Persona 3 is quite sad, especially the ending, poor MC.  
 
Ending of MGS3, true patriot. 
 
When your horse doesn't make the jump in SOTC.  
 
Ending of FFX.
 
Feeling helpless at the end of HL2: Episode 2.  

EDIT: Oh yeah, Majora's mask, felt sorry for loads of people that you then had to help, that game was sad  -_- 
 
Haha I don't play many games, only ones that really stand out. They all seem to be quite sad...

End of Final Fantasy X, specifically...

I was going to leave the country a month or so after I played it, leaving all my friends behind, and I was also hopelessly in love...so that moment stuck with me. The music from that scene is enough to bring me to tears.

I was Tidus.