Feels Trip

[Kreekakon]

This below is not a video game, but I am still going to give it an honorable mention due to the fact that it is to date the only piece of media which has made me cry genuine tears (Not just choked up; It was tears coming out of my face)

Higurashi Kai (Anime)

Spoiler below!

During the end of the Massacre arc during which the group comes very close to success, but ends up failing anyways slowly, and horribly.

Now to the video games!

Walking Dead Season 1

Spoiler below!

The ending, everyone knows this one. When Lee dies.

Fire Emblem Awakening

Spoiler below!

Anytime a scene with this song comes up:
https://www.youtube.com/watch?v=D2sT4ys8oWQ

Corpse Party

Spoiler below!

The entire thing. Poor kids. Poor Seiko.

IB

Spoiler below!

Gary's death.