Some of the bad endings can fall into this, save for the joke endings.
There's something very unsettling in the aforementioned Labyrinth segment in Minoru's route. Failing to pick the correct options will lead you to a chilling bad end. Dying all alone with no one in sight to save you from the depths of nothingness...
Earlier in Minoru's route is the bad end where you plan to meet Toyama at a noodle shop. It turns out he's scorned the head chef there by dodging his bills. Toyama is lucky enough to just be turned over to the loan sharks before you arrive - Minoru, Chiaki, and Katayama are all murdered in the chef's blind rage.
If Kano and Jack arrive at the hide out too early they will hear the fight going on. Kano bust in to find the corpses and a few moment later Jack also falls down stabbed in the back of the head. Kano only have time to realize he forgot to check the bodies before Canaan kill him.
Tateno taking the Tama costume and getting into the warehouse. The music and shot of the bloodied costume as Achi slowly realizes that he killed the whole troupe for the keys and they are now locked with no escape.
Achi getting suddenly stabbed by a kidnapper after taking a wrong turn to avoid talking to Minoru. One frame he is fine the next a foreigner is behind him and his eyes widen as a stabbing nois is heard.
Tanaka finding Maria, depending on which route you start his betrayal is not yet known which makes him turning around and hitting Maria with a hammer even more horrifying.
As seen at the start of Osawa's route, the photos of the people that were infected by the Ua virus. The descriptions of its symptoms makes it even more gruesome even if the photos only showed vague details of said symptoms.
Canaan (actually Alphard) smiling when her true identity is revealed. What makes this extremely startling is that she presented herself as an cool-headed person who displays a stoic and emotionless front to everyone she meets for most of the game.
