Warning: Spoilers Off applies to this page. Proceed at your own risk.
The shadow rifts in general tend to be rather unsettling. Mostly because they take place in a dark void, with floating objects for you to interact with, and are uncannily related to the location or situation you're in when you enter them.
The whole ordeal with the Mobius ring. It culminates in That One Puzzle, but in the midst of all the frustration is the reveal that, at some point in the future, you'll get your hand chopped off (presumably unwillingly) and replaced with a hook. You will then leave that severed hand in a box for your past self to find.
Uncursing the sickle. Previous uncursing sequences were, while completely unrelated to the rest of the game, still ridiculous and silly enough to fit in with the game's style. This one, however, goes straight-up horror: a murderous scarecrow is actively hunting you down, killing you with a sickle whenever you're in one place for too long. You have to travel through the areas previous uncursings took place at, gathering parts for a lawn mower to fight back with, all while you're being hunted.
It's also worth noting: during each of these sequences, rather than being your player character, you've taken control of a separate person. Neither you nor the characters around give any indication of you being any different from normal, making it seem less like you're taking control and more like you're just observing an event. But here, as the scarecrow stalks your controlled character Ashley, it specifically calls you by your name. Unlike everyone and everything else in these sequences, it knows who you really are.
The Maize Maze. It's one long Shout-Out to It's A Good Life, as you travel through a cornfield and find numerous people who got sent there by a boy named Billy. The area has plenty of humor and lightheartedness, with the people stuck in the cornfield being a lot less bothered than you'd expect, but it's still chilling that something like this is going on, and you ultimately can't help besides make the people stuck there a bit happier.
One house in Gray County is inhabited solely by dolls. Dolls that move and talk - albeit only in repeated patterns. You find what seem to be diary pages stuck around the house talking about how the house owner thinks the dolls are trying to kill him and ultimately sealed himself in his bomb shelter for safety. It turns out the "diary pages" were pieces of a novel written by the house owner, who got so into his own writing (which coincidentally lined up perfectly with his day-to-day life with the dolls) that he started thinking the dolls were out for him. Until the very end, though, it comes off as serious.
For those who played West of Loathing, one of the "diary" pages has the dollmaker wondering if the dolls' supposed murderous tendencies are because of the doll he found and based them on: Grace.
The Borge House. The farmer invites you in out of the rain, offering you some spaghetti to eat and towels to dry off with. One condition: you must not look at his daughter. What seems like a typical Farmer's Daughter plot gets turned on its head when said daughter suddenly appears behind you - a Stringy-Haired Ghost Girl who constantly follows behind you, and if you ever turn to face her, you get dropped outside the house's property where the house has completely vanished. You have to make your way through the house, using obstacles to turn around without looking at her, in order to get the spaghetti and towels you were offered.
The whole time, the written dialogue paints a terrifying picture of the sounds the girl is making and just how close she's getting to you.
In the end, when it's just you and the daughter in a room, she suddenly speaks up and says not to believe everything her father says. You end up having to look at her to solve the puzzle, and only in this instance is it safe to do so. And afterwards she says that to take the towels, there is one condition: you must not look at her father. Cue her father suddenly appearing in the room with you, and the two of them just silently stare at you as you make your way out of the house (or turn to look at them, with the same result as if you looked at the daughter earlier). And you never learn anything about what's going on here.
