- The UFO ending. Not to mention, the fact he's asking for his daughter when talking to the aliens.Harry: Let me ask you, have you seen a little girl around here? Short, black hai—AAAARGHHHHHH!!!!
- Meta wise, just the fact that Harrys screams in pain are among some of his most emotional acting throughout the whole game.
- It is easy to find the Bloodsucker in the fridge hilarious.
- Dahlia's ramblings can come across as really out of left field. But of course, it was foretold by GYROMANCY!!
- The idea of a member of the Order attempting to foretell the events described through gyromancy is itself probably the funniest thing in this incredibly dark series. A member of an evil, child sacrificing doomsday cult? Terrifying. A member of an evil, child sacrificing doomsday cult spinning in circles until they collapse onto a letter, then getting up and doing it again until they get a coherent message? Hilarious.
- Some of Harry's internal observations when investigating can be frequently classed under "Captain Obvious", but his comment about the bodies in the morgues and how he "doesn't feel like checking them out" was a rich moment of comedy.
- While it's debatable how lucid Harry really can be in the Otherworld, sometimes his observations have Skewed Priorities and surprising obliviousness. By the time the elementary school clearly shifts to a different, hellish reality covered in darkness and rust, with hanging cages filled with meaty corpses, Harry is baffled by the presence of a wheelchair in an elementary school.
- Examining a shower curtain gives you the helpful info "Nobody inside''.
- Kaufmann accidentally taking a shot at poor Harry, a full second or two after Harry had already put up his hands and said "Hold it!" You almost expect Kaufman to deadpan "Oh. I didn't see you."
- Imagine you're exploring through Nowhere and enter a horrible, rusty storeroom and examine an item on a shelf... only to find a bag of jelly beans. Even funnier is Harry trying to open the bag, only for the beans to spill all over the floor.
- Early in the game, Harry can examine a dog house to retrieve a key. The subtitle reads, "This looks like a dog house, though I can't be sure, since there's no dog around." Ignoring the fact that there are plenty of dogs around, apparently a dog house isn't actually a dog house unless there's a dog living in it.
- The sort of "gag reel" after the credits, at least in the good endings.
Funny / Silent Hill