Basically what the title says. I’ve only played two games like this so far (Silent Hill 2 and OMORI) and am looking for more.
Could be games, ROM hacks, mods of existing games, etc.
EDIT: So many great suggestions! Getting a bit overwhelmed by how many there are, so I’m going to need to find a way to put this in some kind of list with an order to play the games in. By all means, keep 'em coming, though!
I’d have to say Nier Automata, as well as the recent remaster of the game that came before it, Nier Replicant (ver 1.22…). Both are soul-crushing, which is helped by their amazing soundtracks. I definitely recommend them if you’re looking for something to make you cry.
NieR: Automata is also definetely my favourite tip. Especially if you want to cry.
Just as a hint: you need to play until you get ending c or d to experience the full story (and by that I mean, you are literally missing half the story otherwise). You don’t need to do anything special, just keep playing.
Also after you get one you can easily do the other and then get the “true” ending.
