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Let's start off with a lovely little gift from the already-mindfucking ending of Final Fantasy VIII.

Welcome to Hell. Squall will be your guide.

Fucking Case 3 of Ace Attorney Investigations. Dat fucking intro

And the portal series itself. For a game for everyone it can get surprisingly creepy.
Dem Rattman dens

We don't go to ravenholm

I can say nothing below unless everyone here finished metal gear solid 2.

The flood used to scare the hell out of me as a kid.

Bringing kids to screaming tears since 1991.

Can I get away with this? No? Okay, the Half Life 2 zombies.The reverse screams really get me.

Don't you take that fucking mirror!

teapots rattling

Creepy fucking butler from that lara croft game, that shit used to give me anxiety

Minecraft Ambience

Because it means there are scary monsters around waiting to teabag my dismembered corpse.

When Sega Don fucked up in putting creepy shit in kids games:

Albeit gory and not for all ages, Brutal Legend is not a horror game, so….

Every Time Doviculus appears onscreen. Extra points for beeing voiced by Tim Curry

Also, Scylla from Smite

I̛͍̞͈̖͎͔̙ͨ̊ͫ̐ͥ'̡͉ͤ͊͊͑̆ͨM̬̞̗̰͐̚ ̅̏̆͌̈͏̩̘̲̙̺A̦̺͚̞͇͈̟ͪ͡ ̛̻̺̰̪̠̟͊͂̂M̉̀ͩ͐ͨǪ̗͉̈́̉̊̍̎̏ͅN̒ͯ̇ST̙̬̬̙͙ͯ͋͑ͯ͋̚E̟R̢͙̣͛!̘̹̦̣͛̉!͖̟̰̂̏ͨͬ̔̂ͅ!͏̬͍͇̣

@STWaldo
Also, the "history lesson" that Lanayru gives you before you enter the Lakebed Temple. Surreal and disturbing.

The Master Longsword you get is nice, but wasn't worth the trauma to me. That mid-game sequence where you're on the farm as a kid wasn't much fun either. I've heard of something called Terry Cotter's Army as well, but never saw it myself.

Fucking Dead Hands!

And this Silent Realm Guardian from Skyward Sword.

The way it slowly floats towards you, while swinging its swords back and forth really freaks me out.
The Silent Realm is already creepy enough, and then I turn around to see this fucker getting closer!
It's like something right out of my nightmares.

This motherfucking chain-chomp scared the shit out of me when I was younger.

Areas where you're trapped in an empty, formless void. That psychological torture shit should be illegal, bro.

Don't ask.

Doesn't need explanation.

I was once playing Dishonored and passed this civilian wearing a green coat.
Turns out he was actually a weeper wearing the same color coat as the civilian I was thinking of and proceeded to chomp on my arm, simultaneously alerting two other weepers to my presence.
Then after escaping I was promptly eaten alive by rats.

The Boy of Silence appearing directly behind you after activating the switch in the Warden's Office in BioShock Infinite. Alternatively, the entire Shadow Temple in Zelda: Ocarina of Time.

Rare's game over scenes for both Banjo-Kazooie and Donkey Kong 64 are pretty harsh for games made to appeal to kids. Just the fact that it shows the villains actually winning makes it all the more terrifying.

Both incarnations of Zero in the Kirby series. First, the incident of Kirby's Dream Land 3.

And then, in Kirby 64: The Crystal Shards, what appears to be something seemingly cute…

…turns into, well, this.

Fun story. I was playing Skyward Sword for the first time, and I had reached the Lanayru Silent Realm. The last tear I got was in that section with all the Earth Watchers, and one was chasing me as I sprinted towards the tear. Well, I fucked up doing that, because getting it stopped all my momentum because of it activating the mini cutscene of letting you know you just collected the final tear, so when the gameplay resumed, I got caught.

This means I had to make it all the way back to the circle with NO MORE TEARS TO COLLECT. It was a harrowing experience, to say the least -- easily one of the most intense I've ever had in a video game.

--

The Boss Theme for the US version of Sonic CD. It's is a extremely jarring and harrowing track that feels almost out of place at times. For a quick comparison. . .

--

This is the original (JP/EU) track. They're polar opposites. Does the US really think nightmare-inducing tracks like that are fitting for a Sonic game?

Two words…
Nightmare fuel.

Yes, those normally cute enemies from digdug scared the living daylights out of me whenever they would go through the walls. yea that face didnt help at all…

PETER CONFIRMED AS THE SECURITY GUARD OF FF@F3

The third Chapter of The Unfinished Swan.

Evertything was so freakin dark! Too much spook!

The ghost cars of Gta Sa

because nothing is scarier

I know I probably mention Fallout way too much, but honestly, this is the only unused example I had:
Fucking.
God-damn.
CENTAURS!

LUCIFER'S TITS, DID BETHESDA SUMMON H.P LOVECRAFT FROM THE GRAVE TO DESIGN THAT THING? IT'S GOT GOD-DAMN TENTACLES COMING FROM IT MOUTH!

OH GOD I HAVE NO NEED TO ASK [panic attack]

God damn Happy Pig Motel. Like what the hell man, what the actual hell is this.

FUN STORY:
first time i played this and I was like 5, I fucked up in chemical plant zone and this shit started playing. It was horrific.
every time since then when I started drowning in sonic I'd run into the kitchen and put my hands over my ears for 10 seconds because that shit fucked me up. Thank god the newer games have less traumatic drowning music.

I've seen that thing a few times, but I have no idea what it is.

That thing is called Uboa, an easter egg from the game called Yume Nikki.
It appears after doing some things in the game.

Catching Rotom in Pokemon D/P. IMO, the Chateau is already one of the creppiest areas in Pokemon, and catching Rotom forces you to go in there in the middle of the night irl. And dear lord, the music…

Also, couple things from the Mario Galaxy series, of all things:
This place (Again, that fucking music…)

And the little "easter egg" in Galaxy 2's Shiverburn Galaxy…

Wait, what? Let's take a closer look…

What the flying fuck, Nintendo.

Shadelight Cavern from Fable 3. Home of the scariest character in the entire Fable series.

It's more psychological scariness than anything. Not many jumpscares.

I guess you never had a PS2 then…

Speaking of Giygas who @Digoxin had mentioned earlier, here is the music that plays when you're fighting him:

Okay, so, encountering the Spider Queen in Okami was scary enough.
I mean, look at her!

But that's not the scariest thing.
The scariest thing is when you UNEXPECTEDLY ENCOUNTER HER A SECOND TIME AS A DISEMBODIED FLOATING HEAD WHICH ZOOMS IN ON THE WHOLE FUCKING SCREEN.

AND THAT WHOLE SHIP WAS SCARY.
NOT ONLY WAS HER GHOST THERE, BUT ALSO THE SKELETAL REMAINS OF MIGHTY SAMURAI BOAR.

BUT WAIT, THERE'S MORE!
Remember that pile of seaweed that suddenly came to life and tried to crush you?
I truly feared that thing, even after I steamrolled it to death.

Spiders (Many Legend of Zelda games, Skyrim, Fallout, etc.)
Arachnophobia is a bitch.

Let's not forget the Tool "venue" from Guitar Hero: World Tour.

The eyeeeees. Also, this venue is a horrible idea if you're prone to seizures. I had no problems with Problem Solverz for the most part, but I needed to put in eyedrops before playing Vicarious.

I was always afraid to fight Nephtis in Zone Enders 2, normal attacks didn't work and the fact she was moving around to catch you off guard.

Fuck you redeads, fuck you dead hands, fuck you wall masters, fuck you bottom of the well, fuck you Shadow Temple.