Most Depressing Games Ever

[psimaster]

Title says it all. My pick would have to be The Legend of Zelda: Majora's Mask.

[Slime Slayer]

Crystal Chronicals Ring of fate was not a happy ending. I think that's the only game that ever made me well up.

[CrispyChicken]

The Walking Dead (Telltale series) - Only ending to a game that ever brought me to tears
Beyond Two Souls - The whole game is very depressing and everything that can go wrong, pretty much goes wrong.

[bearhawk72]

Shadow of the Colossus has a downer of an ending, especially if you know what happens in Ico.

[ARedLetterDay]

Metal Gear Solid.

[RU Joe]

http://www.retrouprising.com/video-games/reviews/max-payne/t8514/

Although I loved playing it, all the while I was thinking of what a poor guy Max really was.
His family got murdered by junkies who were high on a new designer drug .. that his own partner had some part in distributing - now that's got to be one of the most depressing situations I've come across in a game.

[psimaster]

I got another one: I Have No Mouth And I Must Scream. The title alone is depressing.

[kiwinavega]

This is pretty depressing - and yet uplifting, too.

A small talk at the back of beyond | Adventure Games | Play Free Games Online at Armor Games (http://armorgames.com/play/14925/a-small-talk-at-the-back-of-beyond)

---------- Post added at 08:20 PM ---------- Previous post was at 07:46 PM ----------

This one also has a slightly depressing ending

Pretentious Game | Puzzle & Skill Games | Play Free Games Online at Armor Games (http://armorgames.com/play/13225/pretentious-game)

[Razeluxe]

Undertale (only the demo at the moment) Can be pretty uplifting and/or very depressing depending on how you play.
NieR
Dark Souls, at times.
Ib
The Witches House

I could keep going. My friend and I are always confused how we keep getting sad games without meaning to.

[Kong]

Out of This World and Heart of the Alien

[Dudebro]

I avoid dready or depressing games but I'll second Dark Souls. It's dark and depressing without being pushy about it.

[ARedLetterDay]

I felt that Demon's Souls had an overall much more depressing atmosphere than Dark Souls.

[Kugyince]

Absolutely breathtaking and solid proof that video games are an art form and can evoke emotion:

To the Moon - Trailer - YouTube

[joz]

Shaq Fu

[RU Joe]

I came across the instruction book for this one in the junk drawer, and immediately thought of this thread:

Rogue Trip Vacation 2012 (Intro) (PS1) HD - YouTube

It is the year 2012.
The world is crumbling into a new Dark Age.
Disease and poverty run rampant in a world scourged by desolation, pollution, radiation, and despair.

But HEY, don't let that spoil your day, take a VACATION!!

Are you literally dying to go on vacation?
Well now's the time to make your dream come true with a luxurious visit to one of Big Daddy's Vacation Wonderlands!

By the sweat and blood of those zany, wacky, oppressed lower classes, Big Daddy's made his little paradises shine like gemstones amidst the teeming crud of our sad little dying world!

Aren't you glad you can afford it?
So call now, operators are standi ..

HEY LOSERS, need a vacation?
Can't afford one of Big Daddy's snob fests?
Don't despair, fight back - hire an Auto Mercenary!

These professional party crashers will hijack you on a high - speed, high - thrill, totally unauthorized vacation deep into the very heart of Big Daddy land - and at a fraction of the cost.

Our tricked - out battle rigs are fully loaded attack vehicles, armed to the teeth and ready for anything Big Daddy can throw at us.
We fight the fight, so you can see the sights!

This has been a totally illegal, unpaid announcement for the Amalgamated Association of Auto Mercenaries.
We now return you to your regularly - scheduled crap!

[KATZ]

Heavy rain for me

[kiwinavega]

Ooo, just remembered - Fahrenheit on PS2 (I think it was called something else in the States - Indigo Prophecy, perhaps?) was pretty depressing. Brilliant game though.

[Jack Bando]

Papers, Please