Competing in the Man Festival in Shadow Hearts: Covenant and finding out that the punishment for losing is:
a buggering
Then discovering the the prize for winning is:
a buggering
You're buggered if you win... you're buggered if you lose... but you only find out when it's too late to back out of the Man Festival, so you're going to be buggered no matter what happens.
It certainly is a unforgettable moment in gaming, but it's also pretty damn disturbing because, no matter how much they try to cover it up with euphemism, funny music and comedy sound effects, the underlying tone is pretty sinister and dark, especially as the punishment or congratulatory buggering takes place in front of the rest of your party (possibly including the 14 year old daughter of the Tsar of Russia, Princess Anastasia Romanov).
For me it was the reveal that Alexia Asford was actually her brother crossdressing as her because he couldn't accept her death (Resident Evil Code Veronica). That was just insanely fucked up.
Great but scary scene.
4-5 years ago when I was at a friends house, we were playing WoW. We were new to the game and was searching for the deadmines, since it's entrance isn't exactly the most visible one.
When we finally found it we both simultaneously said "The deadmines" without realizing it at first.
The most unforgettable and disturbing part of gaming for me, sadly? Grand Theft Auto IV: The Lost and Damned, when Mayor Stubbs throws off his towel in the steam room, and your confronted with what looks to be one of the hot-dog models attached lovingly to a human form.
All humor aside though, one the most shaking moments for me in gaming would have to be something along the lines of:
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