While I can name off many games that really made me sad through the story/ending such as Silent Hill 2, MGS3, S.T.A.L.K.E.R. Shadow of Chernobyl, and a few others the one that has always stuck with me is Conker's Bad Fur Day for the N64. Most of the game was happy-go-lucky movie rip-offs that were hilarious and fun to play but when it got to the ending it horrified me when I first played it. I couldn't believe at how such a carefree game became so dark and depressing in the final moments.

Here's the ending (I suggest you play the game and experience it yourself, but it may be hard to find. I still have my original copy and I love it to death, but if you don't have an N64/the means to get it, go ahead and watch to see what I mean.)

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Zone of Enders was pretty depressing at the end....actually the whole story was depressing....gah

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To be very cliche but probably Silent Hill 2.

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Blood for the Blood God! Skulls for the Skull Throne!
There he goes. One of God's own prototypes. Some kind of high powered mutant never even considered for mass production. Too weird to live, and much too rare to die.

Hah as funny as it sounds, Klonoa: Door to Phantomille is super bleak towards the end. It looks like a dumb cutesy game but it gets all weird and dark towards the end. Adorable kitten boy isn't so cute when he's screaming over his grandfathers corpse. It's a horrible contrast with all the cutesy music and environments and stuff. In the end the obnoxious little space boy confesses at how they had just used klonoa in a manner all too similar to Tidus from FFX. They tell him that he's not real, is like a bad dream and can't exist in the same world as all of his friends and he ends up just screaming and struggling and getting sucked up into the sky.

SUPER BLEAK.

It's mainly the endings that get me all gloomy.

I agree that MGS3's ending is definitely depressing. Metal Gear Solid 4's "first ending" almost had me in tears. YOU KNOW WHAT I MEAN.

I found Deadly Premonition's final episode and ending (don't judge) to be extremely tear-jerking as well.

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Earthbound.

"Your attacks are absorbed by the darkness..."

"...I feel... H...A...P..P...Y..."

"You cannot grasp the true form of the attack!"

Ness started crying uncontrollably!
Paula collapsed!
Jeff's body went numb!
Poo took 156 points of mortal damage!

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Fight the monster, become the monster.

The entirety of "Dear Esther" (originally a Half-Life 2 mod, now a standalone indie game) is pretty depressing. Just you, a deserted island, no inventory, no health indication, barren fields, wide open spaces, and a drowzy and highly subjective narrator's voice inside your skull, lulling you sleepily into the heart of a secluded cave.

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I agree with you there. It was very depressing.

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BY FAR the most depressing ending I've ever seen is the extended ending of Kane and Lynch. I'm getting depressed right now thinking about it. I'm convinced the ending is the reason nobody gives it the credit i think it's due.

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This is true, for both games part 1 for its ending and part 2 for awful it was, depresses me that i wasted 5 bucks on it

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