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[Iduno]

I'm sad they put so much effort time into Stellaris, and it's still not a remotely good game. It feels like it should be, but it's like they took everything good and made sure it didn't work the way players would want.

More what you're looking for: Analogue: A Hate Story. Once you find out what happened and why...

[KingofstarrySkies]

that's not
that's not really the point of the thread i feel like

[NullForceOmega]

The Final Station.  Man, that game was an experience.

[nenjin]

Didn't make me sad per se, but Spec Ops: The Line left me feeling like shit afterward.

[Folly]

To the Moon - An excellent sad game.

Final Fantasy X & X2 - The music really sold me on the relationships between the characters, which made the ending all the more tragic and the epilogue all the more moving.

Drakengard - Nier has already been mentioned in this thread, but all the games from this series have tragic overtones.

Bioshock - Another series of story-driven games with tragic endings.

That Dragon, Cancer - A sad game made all the sadder when you learn that it's based on a true story.

Braid - Feels like an ordinary platformer, up until the twist ending...

[AzyWng]

Metro 2033’s “Ranger” ending. Thankfully this is the canon ending and sequels continue from this point (so all is not lost), but since you just did what was done just two decades ago (used a set of missiles to obliterate your foes)...

It’s not that something was lost when Artyom launches the missiles.

It’s just that what was lost over two decades ago has failed to return.

Fallout: New Vegas - Dead Money DLC’s ending.

Yes, I’m glad I don’t ever have to stroll through the hell known as the Sierra Madre ever again for that play through, but I also never meet Dog/God (whatever you do, one or both of them disappear, and neither of them are exactly inherently wicked), Dean Domino (He’s an asshole, sure, but he’s kind of cool all the same, and does still deign to help you so long as you’re nice), or Christine (Who’s basically been dealt such a bad hand two bullets in the head might almost qualify as mercy) ever again.

I always thought of that as a damn shame.

[Wiles]

I have probably forgotten most sad moments I have had in gaming, but I do remember the first one, which happened while playing Falcon 3.0 (Maybe the Hornet Naval Strike Fighter version? It was a long time ago).

I had finally managed to properly configure my sound card so that all of the sound in the game worked. I could hear the radio chatter! I remember marveling over the fact I could hear my wingman talk to me, it made the whole experience more immersive than any other video game I had played up to that point. Then my wingman was shot down, I heard him exclaim something to the effect of "I'm hit!" and crash into the ocean. 8 year old me was sad.

RIP Wingman, you may be gone, but you are not forgotten.

[Rince Wind]

Doki Doki Literature Club 

[Enemy post]

To the Moon - An excellent sad game.

This one, absolutely.

Also Walking Dead Season 1's ending and Mass Effect 3.

Mass Effect being for...multiple reasons.

[Il Palazzo]

Sad as in cathartic sad?

Year Walk.
It's a couple-hours long experience, best played on a lonely snowy night. Ideally on New Year's Eve.

[Levi]

To the moon. 

[Aoi]

I'm skipping visual novels because ending miserably is a common thing with a lot of them...

Into the Breach. You're skipping from dimension to dimension and across timelines trying to fight off an alien invasion (or were they sleeping in the earth already?)... but what happens every time to use your reset button? A timeline forks because you decided you didn't like your move and want to try something else... and one timeline waves goodbye to their last hope of survival. Good job, hero: You just condemned a few billion humans to their doom. And after you save the world? You do it All. Over. Again. You never rest until you die. And then there's the idea that these alternate timelines aren't spawned until you create them, so you're splintering timelines and potentially sending billions to their doom each time in trying to achieve some kind of sadomasochistic absolution for yourself?

Papers, Please. Which would actually be more sad if I didn't start mentally cursing out my family and saying "You don't need to need EVERY day, do you?"

An oldie: Lufia 2: Rise of the Sinistrals. Still one of the greatest RPGs, I'd say. A ton of stuff ahead of its time. Character development that actually goes somewhere. And sad spoilery stuff.

[cider]

What Remains of Edith Finch is a game where a young woman (Edith Finch) revisits her ancestral home and learns of the fates of her dead relatives. Each of these fates play out as their own little story inside the game, with unique gameplay elements. Some of the stories are better than others, and one about a worker at a canning factory is both beautiful and very sad. A masterpiece portion of an otherwise very good game.

[A Thing]

Yakuza 0 is the most recent game in memory that made me cry. Despite being the goofiest shit most of the time, the ending is a surprisingly poignant and emotional summary of the themes of the entire game.

Spoiler (click to show/hide)

Not being able to change, but not wanting to become worse for example.

Persona 3 gets a mention too, although unlike Yakuza 0 I entirely expected a tragic ending to that game from moment 1 so it didn't hit me as hard.

[DeKaFu]

I legitimately cried at several points in Dark Souls. Not from frustration (though maybe that too), but because I had decided at the start that I had to protect all the quirky friendly NPCs that were the little spots of brightness in that dark world - and then proceeded to fail that task utterly. I absolutely took it hard every damn time.

Ib is another game that really got to me in places. It was the first horror game I played where I was so attached to the characters that I was legitimately scared for them (rather than through them by proxy). It has multiple endings, and some of them...