Funny / Silent Hill
- The UFO ending itself. 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!!!!
- 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 for this creeped-out troper.
"The lock is jammed. The door cannot be opened."
...almost reaches Running Gag
levels. It's almost funny how many doors Harry is unable to open.
- Examining a shower curtain gives you the helpful info "Nobody inside''.
- Kaufmann accidentally taking a shot a poor Harry, a full second or two after Harry put up his hands and said "Hold it!"
- 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 ending.