Just look at Bobby Ricks go wide-eyed before Pyramid Head cuts the cake. It's impossible to tell if he's scared or simply worried about the cake.
As disturbing as he/it is, Monocle Man saying, "Did you enjoy the ride, Murphy?" is weirdly funny because of the sarcasm and because it comes right the hell out of nowhere. You wouldn't expect something like that from a Silent Hill monster.
During the final boss, Murphy runs along a catwalk lined with cells. Each of the white cells contains a Wall Body who blocks your progress for a bit. There are enough that you get used to it, then you approach the last one. It opens and... nothing pops out. No Wall Body. He's in the very next cell you pass. While not hilarious, it'll catch you off guard, and might even make you laugh.
If you look into the cell of a Wall Body that has just retracted in, you'll see it spin around like a coin. It's pretty surreal.
Murphy's reaction to seeing the only non-enemy Doll lying in a chair:
"Looks like someone has... specific taste in entertainment..."
In the Devil's Pit Diner, there is a menu on the wall that reads: