Re: Saddest Games
outright sad? I don't think i've played something like that, so far.
Limbo had some bits of sadness, but overall it was more of an unsettling experience.
The end of my relationship in Vampire Bloodlines with this girl was sort of sad but more an upsetting event.
Very farfetched sad is the load scene story segments of PB Winterbottom. With this pie crazy Mr. Winterbottom and the starving kids on the other side.
Grim Fandango was rather melancholy than sad?
The end in Mafia 1. It was justified to not survive but overall he was not a giant asshole like other Mafia heroes are.
Also would name World of Goo. The Goos were sort of pitiful creatures/resources in the weird story.
Not exactly sad but very disturbing was the tiny hidden room showing the past of Agent Vodello in Psychonauts. Imo the most horrifying scene in a game ever.
The end of HL2 Ep2 was the first time HL revealed to me what others liked already since the first one: Valve can tell a good story if they do more than just through in some mysterious loose pieces. If HL2 and Ep. 1 would have been better in that regard i guess this would be number one on my list, but as it was this honor goes to:
Most close to true sadness comes the Luma story of Mario Galaxy 1. No hours long epic cutscenes but it hits every note precise and with feeling.
I guess games lack very very often fully developed characters we can really care for, so being genuinely sad (or having any other meaningful reaction) for any event happening to them is hard.