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Amnesia: The Dark Descent
Pretty much whenever a let's player gets scared by this game. In fact, here's a compilation of reactions.
The new add on must be seen to be believed.
The Water Scene Made even more funny with the subtitles. A Let's Player being freaked out by water demons never sounded so hilarious.
The Custom Story Dark Room. Pretty much Meme Mania.
No game has perfect AI, and the grunt's can be exploited to hilarious results, such as getting it to break down an open door, hiding behind a table in a corner, and piling up a bunch of stuff, then attracting its attention. That last one can occasionally cause it to smash it all, which then freezes it in search mode.
Anytime someone trolls the monsters. Also, replace the chase music with Yakety Sax and the monster sounds with the guy from Yelling At Cats.
The Small Horse series of custom stories. Starts off with a ship captain finding and bringing home an Eldritch Abomination that looks like a little pink horse, with the help of a bald German guy, unwittingly unleashes a great evil by doing so, and must now fix his own mistake by embarking on an epic quest that involves lots of ponies, hilarious Jump Scares, Pokémon, flying naked corpses with extendable necks, mining for boulders using the Master Sword, Legend of Zelda-esque dungeons, engineers and sentries, zombie Fluttershy, a crazy race track, the Space Core, Daleks, and a giant suit of armor that likes to jump out and yell "Hello!" when you least expect it..
Once Daniel enters the Cistern, a flashback occurs.
Daniel: You are conserving water from the spring?
Alexander: Yes, it enables me to control the water in the drain sewers to some extent. Also, it can be used for all sorts of purposes.