'''As a Moments subpage, all spoilers are unmarked [[Administrivia/SpoilersOff as per policy.]] Administrivia/YouHaveBeenWarned.'''
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* Near the end of the game, Murphy is finally close to resolving his grief over his deceased son. He meets with a Nun that eerily knows a lot about his grief:
--> '''Nun:''' "Thank you for coming to shepherd your son home, Mr. Pendleton. I know it's difficult losing a child..."
--> '''Murphy:''' "With all due respect, I don't think you do, and like I already told you, there's been a mistake, I buried my son years ago."
--> '''Nun:''' "I understand Mr. Pendleton, we all deal with grief in our own way."
** Later during the same scene, [[MotiveRant Murphy finally breaks down]]:
--> '''Murphy:''' I get it, I screwed up! But I didn't see any other way! You don't know what it was like... to know it was my fault he was gone. Every time I shut my eyes I saw Charlie's face, and all I could think was "That monster's still alive, but I'll never get to see my boy again"...
** Followed by Murphy's solemn, tearful HeelRealization.
--> '''Murphy:''' "[[PayEvilUntoEvil What I did to Napier]] didn't solve anything. Charlie was still gone, and I was stuck in prison. Everything spiraled out of control, [[MyGodWhatHaveIDone it was my fault]], I just want... want my life back."
--> '''Nun:''' "[[CycleOfRevenge Revenge is a long, treacherous road]], isn't it Mr. Pendleton? Where do you suppose it ends?"
* At one point, in the Monastary, you can hear what seems to be Charlie crying out for Murphy's help, saying "Daddy! Help! Make him stop! He's hurting me!"
*
--> '''Charlie:''' "You did it! [[PapaWolf You killed the Bogeyman!]]"
--> '''Murphy:''' "Doesn't matter. It won't bring you back. Nothing can bring you back."
--> '''Charlie:''' "[[YouAreBetterThanYouThinkYouAre It's not your fault.]]"
* In the prison level, you can find a note from Carol, Murphy's wife. In it, she rants about how it's all Murphy's fault Charlie is dead and how she will never forgive him and how he should not have even asked for forgiveness in the first place because he doesn't deserve it. She's completely and utterly wrong in her accusations, but the whole game up to this point has shown that Murphy believes she's right.
* When the little boy in the Monastary dies. Murphy desperately tries to remember the Bogeyman rhyme, it's heartbreaking. Especially near the end of the cutscene when the boy is killed and Murphy begins calling out his own son's name with grief.
* Anne's revelations about her father [[AndIMustScream ending up as a vegetable]] after being savagely beaten near the end of the game.
--> "I had to watch this wonderful man shit and piss all over himself day after day ''after day''."
* Anne breaking down in tears after nearly executing Murphy, doubly so on a second playthrough when the player knows what her story is.
* Early on, there's a poster for a missing dog. And only minutes later in the house, you find the bloodied dead body of a dog on a bed… oh.
** There's a police dog locked in a cruiser in the garage of the Centennial building that barks at Murphy should you investigate. After you get the Security Card, some Weeping Bats swarm the area, and you hear it yelp. Then you see the poor creature's bloodied corpse. This game series does not like animals. With luck, the dogs weren't real, given it was set in the Fog World of Silent Hill.
* The revelations of the "Ribbons" sidequest.
* Murphy's flashbacks. You know the ones. Not to mention how Silent Hill seems to take extra measures to rub it in and show him increasingly disturbing hallucinations and Otherworld features to remind him.