cross-posted from: https://hexbear.net/post/728358
My vote goes for Tomb Raider II and the floating islands levels. The game is a relativity normal globe trotting affair for Lara until she gets transported into the fucking shadow realm here. This level gave me major scares as a kid since you're traversing a giant void being chased by animated statue warriors out to kill you.
This is gonna sound dumb but I was scared of that Captain Crunch Adventure game when I was a kid. I thought all the animations were extremely uncanny and off-putting. It was on my cousin's computer and I didn't play it much after The Cap'n introduced the game in the cave, because it was just Not Right.
On the trend of Tomb Raider having creepiness, TR2013 definitely did. It even had a scene ripped straight out of The Descent, which itself was paying homage to Apocalypse Now.