* CrowningMomentOfFunny: The UFO ending.
** The Crowning Moment Of Funny to that: the "Silent Hill Song" at the end credits, which is sung like a children's song that takes AlternateCharacterInterpretation to the depths of hilarious insanity. "[[http://www.youtube.com/watch?v=X_eOpM7qQHo A Sirent Hill no uta, minna ta utaou~]]"
* Some of the characters' words and actions are pretty goofy, but the one that takes the cake for me is when Heather and Douglas are in the hellish, rusty Otherworld, and Douglas has broken his leg. Heather suggests calling an ambulance. I'm really not sure how she expects that to work out.
* The blood in the restroom can be darkly amusing because, since it's the ladies' room, there's an actual non-fatal non-supernatural reason for there to be blood.
* In a callback to ''SilentHill2'', if the player has a save file from [=SH2=] on the same memory card and examines a certain stopped up toilet in the shopping mall, they get the option to have Heather reach inside to remove the blockage. If you select yes, a cutscene plays. Heather is about to reach in the toilet, but stops short. "This is ''way'' too gross." She then turns and looks [[WhatTheHellPlayer straight at the player]] and says "Who would even think of doing something so ''disgusting?''"
* Heather's reaction to finding a dead, barbecued dog in a restaurant.
--> Who the hell would make something like this? Furthermore, who the hell would eat it?
* Heather's [[SkewedPriorities weird sense of priorities]].
--> '''After receiving a creepy "Happy birthday" message over a disconnected phone in a bloody locker:''' "But... [[ComicallyMissingThePoint it's not my birthday...]]"
* From examining a certain object at the amusement park:
--> "There's a dead body inside this box thing. [[SeenItAll There's nothing interesting here]]".
* The map for the church area is downright hilarious, looking like something a child drew while at day care.
* The results of the KonamiCode. Douglas is stripped of shirt and pants, leaving him in only his boxers beneath the trenchcoat. Sucks the serious right out of any cutscene.
** Combine that with Heather's unlockable Princess Heart outfit for extra silliness.
* Claudia's introduction. She introduces herself like she's dropping a huge bombshell, but neither Heather nor a first time player will know who the hell she is, so Heather's reaction is...unimpressed, to say the least.
--> Claudia: (Raises arms dramatically) I...am Claudia.
--> Heather: (Raises arms dramatically) So what?