Scare maze is the only game to ever make me "jump" https://www.fugly.com/flash/709/Scary_Maze_Game.html
It's a tough choice, but it's one of two games. Both made me jump, but I don't remember which did it first.
First, there's the Atari 2600 game Haunted House. When the stupid ghost suddenly shows up and starts chasing you, it can definitely cause a jump. The more experience you had with that damn ghost, in fact, the more it made you jump, lol.
And then there's the arcade game Sinistar. I don't even think I was playing it when it first made me jump; I just happened to be in an arcade that had a Sinistar cabinet in it. It was a silent moment (I think I was the only person in the arcade at this moment) when suddenly I heard that demonic voice, loud as day...
"BEWARE, I LIVE."
"RUN! RUN! RUN!"
Man, did that make me jump. And hearing it always creeped me out from that point forward, whether I was playing the game and Sinistar got completed or if I was just hearing it in an arcade somewhere. I'd still probably be a little creeped out. Man, I miss it. It was a super freakin' hard game, though.
I'd say the first one would be Stonekeep in the caves area where there's a monster lurking underwater and until your drain the water you can only see tentacles popping out randomly.
The real horror started when I got Resident Evil 2, that one was truly memorable with the jump scares.
Good shout on Sinistar - that brings back memories of two-player Saturdays in the local arcade, feeding in the 10p for "just one more go". Sinistar himself was truly terrifying though. All that mining, all that work, then boom, he slams into you and game over...
The first game that properly made me let out a tiny bit of wee was probably the original System Shock though. There was one point in the game where you walked past drone after drone down these corridors and the whole time you're sure they're going to come alive. Then you get to a room at the end, activate a switch and sure enough, there's Shodan screaming at you Max Headroom style and she activates every goddam drone at once. Terrifying. Think I used every single grenade in my inventory, panic stricken. I do seem to remember surviving though. That game was amazing, especially for its time.
Otherwise, most of my big scares came from the likes of Doom, Heretic or Hexen. The latter in particular had some great jumps - there was an arena level with bloody massive minotaurs coming at you - great stuff, but you never knew where the next one would pop out from and they were insanely powerful.
I think my first gruesome gaming memory was Doom, yet I don't recall it truely spooky. Probably on the "horror" experience side, the original Alone in the Dark and a little bit after that with the Resident Evil on a friend's PlayStation are the ones I remember the most as a new kind of sensation when playing.
However, the fear those inspired were nothing compared to the terrifying sound produced when discovered by a soldier in the first Metal Gear Solid. Never jumped so high from a sofa before.
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