In Enderal (an absolutely amazing, totally free game that runs on the Skyrim engine - if you own Skyrim you owe it to yourself to play Enderal), at the end of Esme's questline, sitting on top of the lighthouse and discussing the events of her story.
Esme quest spoilers
If you've ever had a loved one who struggled with mental illness or depression, and you just couldn't help them, it hits like a ton of bricks
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I'm not really a crier when it comes to games, but what brought me close most recently was when I was doing a run of the entire Metro trilogy for the first time.
Spoiler ahead for Metro Exodus
If you're doing the good ending run of Metro Exodus, then you spend most of the game beating the odds and being able to save everyone...
So watching Colonel Miller, someone you become fairly attached to throughout the series, succumb to radiation poisoning while you drive out of Novosibirsk, knowing that there was absolutely nothing I as the player could do but watch was heart-wrenching.
He'd completed the mission, but he just couldn't make it home - it's such a bittersweet ending, but including his speech at the end, it's a good one.
Among the Sleep - Game hinted at the ending which made me cry multiple times and ball when the ending happened.
Yakuza 0 - When she finds the wrist watch
For me it was The Last Guardian's ending.
Breath of the Wild, during one of the memories.
Also Undertale. Left me with a large mess of feelings at the end.
Phantom Brave, when Marona finally makes a real friend. I lose it every time.
About half of GLaDOS's scenes in either Portal game.
Half of Kaim's dreams in Lost Odyssey, and the cliff flashback.
Earthbound. Was playing it as a kid and didn't have a guide. Final boss, was losing. Hit "pray" in a panic because I was out of options. And then it does the whole thing, and something about overcoming impossible odds with the power of love and community gets to me.
Also the ending of the binding of Isaac where you hear his parents fighting. That dredged up some feelings I didn't know were kicking around down there!
Playing against Xero on Nightmare! setting.
Probably one that doesn't get recognized much. In Anachronox, when you find out what happened to Fatima on "that night".
Kanon, Air, Clannad etc
Mother 3 may be the only game that made me teary. I think there may be another I'm blocking out but I generally avoiding trying to be sad
The ending of Pokemon Mystery Dungeon. Such a wonderful soundtrack an story.
I don't remember that happening
The end of LA Noire got to me. I still can't play the last case without tearing up.
Final Fantasy IX. Just... everything to do with Vivi and Quina. Those to characters cemented IX as my favorite in the series after initially writing it off as inferior to VII and VIII. While those games have some great narratives, Vivi and Quina both do such a great job of exploring what it is to be human, in their own beautiful and heart rending ways.
The entire experience of Outer Wilds.
So many parts of Persona 3, 4, and 5, but especially 4.
Here's a weird one: Starflight on Genesis. Not so much because of the story or content, but because I played this game so much with a friend of mine in middle school, and had all but forgotten about it. I was playing through some old Genesis games a month or so ago, and started this game up. As soon as the title screen came up, a flood of memories washed over me and took me right back to 1992. Bawled like a kid for about ten minutes as I realized I had an awesome friend that I had basically completely forgotten about.
Genshin has had me tearing up in a few of its main story quests, beautiful game
A game has never made me cry, but movies and shows make me cry all the time. Even the most emotional game just doesn't come close to other mediums.
One of the biggest ones that permanently etched in my mind from childhood is the ending to Metropolis, especially when that one Ray Charles song comes on.
"Trust me."