Your saddest moment on a videogame

I killed me Shadowmire in Skyrim trying to jump of a mountain :'(

Don't want to spoil a thirty five year old game (give or take a year or so) but that bit in Planetfall...

Bioshock 1 ending
Pillars of Eternity - really should've been obvious to me, but for some reason it wasnt. when I finally got Eder to the record keeper in the first city

Mmm, I'm not sure if this really counts, because it's not technically something in a game, but, it's one of the few video game related things that has legitimately brought me to sorrowful tears.

I've played World of Warcraft on and off for many years, but my most memorable times in the game were during the Wrath of the Lich King expansion in 2008-2010ish. Back in those days I was part of my brother guild, the Radical Dreamers. We had a wonderful little group of friends in the guild that we met from around the game. Many grand times were had with our guild, whether it be running around doing old content for funs, or trying current content and getting cornered in a circular room. I could go on forever about our fun and hilarious times. Sadly, nothing lasts forever. My brother and I stopped playing part way during the Cataclysm expansion, and since he was the guild's leader, the guild ended up falling apart.

A couple years later I started playing again during the Mists of Pandaria expansion. I discovered that one of the old guildies still played so I spoke with them to do some catching up. After some reminiscing, I asked if they kept in touch with anyone else in the guild, and then they told me something that brought me to tears. Two of our guildies were a married couple. I found out that they had both passed away. Hearing this just broke me, even typing about it is bringing back some tears. My guild was like family. Finding out that some had left our world, I just couldn't.

Again, I'm not sure if this really counts, but when I think of the saddest things video game related, this will always be the first thing that comes to my mind.

One day, i was playing Legend of Zelda. I was 5 years old. I was travelling the world with my Cucco. It was the life, but then it all changed. I was at the Water Temple. It was 2:54 when my Cucco left me. I was heart-broken. Everything was ruined. I hated life. Then i got a Yorkie and EVERYTHING IS AWESOME!

Dropsy Right near the end

I cried like a baby @ Eternal senia ending to be honest ...

Nothing particular stands out as the absolute saddest.

Ghost Trick managed to blindside me near the end, definitely worth checking out for anyone with a DS.

The first one I ever experienced was:
Sniper Wolf in Metal Gear Solid, Playstation 1.
Never got far enough in FF7, so :/
Brothers - A Tale of two sons was terrible too.

Not in the same way you meant via character or story. But for me the saddest event in video game was when NCSoft shut down City of Heroes. Lost a family in a way when that happened.

The suicide ending of the stanley parable.
The neutral/scarifice yourself ending of bioshock 2.
That bit in mass effect 2 where you overhear the asari talking with her salarian dad.
The first five to ten minutes of ori and the blind forest.

also, this isn't gameplay-related, but it is games and it did make me sad (although honestly, its kinda dumb why it made me sad). there was a game in early access recently called moonrise. it was a really fun pokeclone with well-designed critters and had so much potential. the devs shut it down because it wasn't making constant profits. didn't try to find another solution or offer refunds. it was the first time i'd ever seen a good game get pulled from steam, and i'd put so much money into it in hopes of seeing it succeed that it kinda hurt when it crashed and burned. then fnaf world, another really fun and cute game with great character design, got pulled, and i had ANOTHER bout of "crap thats sad" that was mostly brought on from memories of the aforementioned moonrise experience, even though the situations were completely different. the former game is never coming back because the devs can't manage money, the second game is coming back completely free and updated, so i didnt really have a reason to be sad. such is life.

Can't really remember something in particular, but the ending of Warp...

To The Moon. That's all I'm saying.

Warcraft III Reign of Chaos when Arthas turned Sylvanas into a banshee.

No, wait. I was pissed off, not sad.

Diablo III where Leah turns out to be Diablo's daughter and she ends up being the vessel through which he comes back to the world so she effectively dies.

No, wait. I was pissed off at that, too.

It'll come to me eventually...

Metal gear solid 4 ending Big Boss die :''(

mass effect 3 ending, bioware's fall

Brothers, Transistor, Walking Dead 1, Undertale. I cried more, than a grown man should have. And I replayed Transistor two more times - always the same effect. T_T

Gravity Ghost, towards the ending as the story unfolds.

to the moon. without a doubt

Aerith

Celes' suicide attempt scene in FFVI.
Apart from the sheer WTF factor of it, the ending sequence of Transistor.
The ending of Syberia II. More of a bittersweet one though.
To the Moon's… well, mostly it's second half. Although the implication of a few-frame deliberate flash scene in the second minisode may even top it.

This may be the only thread where the spoiler text has been used appropriately.

I am a highly emotional person when it comes to stories and characters, so there are a lot I have been affected by. But one that immediately comes to mind is Brothers - A Tale of Two Sons. Oh my gosh, I was bawling my eyes out at that.

Bad end on Rannoch in Mass Effect 3