'''As a Moments subpage, all spoilers are unmarked [[Administrivia/SpoilersOff as per policy.]] Administrivia/YouHaveBeenWarned.'''
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* The Surprise ending, one of the best secret endings in the franchise and a hilarious scene to boot.
** [[http://princessstabbity.tumblr.com/post/19717157945 Look who gets to cut the cake!]]
*** Just look at [[https://www.youtube.com/watch?v=ApxI-jeRCxE 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.
** Also, the fact that this hideous disembodied NightmareFace is wearing a [[ExactlyWhatItSaysOnTheTin monocle]]. [[StockBritishPhrases I say]]!
** He's even funnier if you've seen Cassandra from ''Series/DoctorWho''. You can't help but picture him saying "Moisturize me, Murphy!"
* The cardboard Bogeyman. Complete with little cardboard [[WrittenSoundEffect sound-effect bubbles]] when he swings his hammer.
* When you're digging up Silent Hill artifacts, at some point you come across a little UFO. Murphy quips, "Abduction, huh? That's one way out of here, I guess..."
* [[https://youtu.be/yMgAz5I2JyQ?t=10m22s The Prisoner Juggernaut unwittingly demonstrating its vulnerability to electricity. And gravity.]]
* 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:
-->''MONDAY - Meat''\\
''TUESDAY - Meat''\\
''WEDNESDAY - Meat''\\
''THURSDAY - Meat''\\
''FRIDAY - Boiled meat''\\
''SATURDAY - Rain''\\
''SUNDAY - Fog''
* Murphy screaming his lungs out as he is being chased by the Void in the Otherworld segments? Terrifying. The game getting bugged, [[https://youtu.be/gqYCIwurfV8 causing Murphy to scream every two seconds for no reason as he walks around a building in the normal world]]? Fucking hilarious.
-->'''Video Description:''' He just wouldn't shut up, I could've beaten the game this way.