- Poor little May and her horrible Family-Unfriendly Death.
- Same goes for Albert and his blind mother: he gives her a shawl, only for both of them to be violently murdered moments later by Corroder.
- Phillip's death scene. Especially Nancy's line just before it, "Phillip darling! Father! Alyssa has laughed for the first time!"
- Seeing Alyssa's mother die right in front of her. The worst part was Alyssa and Dennis totally downplaying it in the ending.
- The scene leading up to the final level. Alyssa has soothed the spirits of the ancient Rooders who were slain in previous Rituals of Engagement and after maybe or maybe not being dead, Nancy finally reunites with Alyssa... Only to be ripped away by the Dark Gentleman, who then teleports Alyssa back to the clock tower. Hearing Alyssa crying out for her mother once she realizes that she's been taken again is just heartbreaking.
- Finding out that in the intervening time between reuniting with Nancy after defeating Chopper and making it up to the top of the clock tower, Dick has sealed Nancy's soul into a statue. As if that wasn't bad enough, he then obliterates the statue just to rub salt into the wound. Unfortunately for him, this pushes Alyssa to her breaking point and she fully embraces her role as a Rooder, And Nancy is still able to give Alyssa the power she needs to finish off Lord Burroughs and Dick for good and save her mother's soul.
- Unlike the other Subordinates, it's stated outright that Robert Morris had no history of violence before the sudden murder spree that resulted in his execution and subsequent rebirth as Sledgehammer. In all likelihood, he was just an ordinary man with relatively few issues before he was possessed by an Entity and driven to kill.
Tear Jerker / Clock Tower 3