- "This town is full of monsters! How can you sit there and eat PIZZA?"
- A particularly memorable use of Victoria's Secret Compartment has Maria pull three keys from her figure (one each from her boots, her miniskirt and her cleavage), all while James tries none-too-subtly to sneak a peek.
- "Why you... You... You fartface!"
- The Dog Ending. James goes To Hell and Back, only to find that his experience was engineered by a Shiba Inu dog. The credits then play to the background music of a hilariously out of place upbeat tune "sung" in dog barks.
- Not to mention what plays alongside the credits, with a small screen displaying what appears to be early, buggy development footage and a hilarious photo manipulation of James sporting the body of a hyper-muscular body builder. The song also briefly stops when the dog starts growling at pictures of Eddie, one of which focuses on his stomach.
- The UFO Ending, complete with retro-blocky-graphics Cameo, antiquated and badly out-of-tune music, and a Catch Phrase exchange. (James would return the cameo favor in both Silent Hill 3 and Silent Hill: Shattered Memories.)
- In the instruction manual, James's occupation is listed as "Protagonist".
- Curiously, every character's occupation and age (except for James's) is listed as "unknown" in the manual. One wonders why they even bothered.
- James's questionably diplomatic question to the armed psycho: "Eddie, have you gone nuts?"
- When James moves while swinging the plank, it looks like he's a parade marshal twirling a baton. A demonstration.
- When travelling Nathan Avenue with Maria, shortly after passing the sign for the Lakeview Hotel, Mannequins start getting flung at you from over the fences in a manner that makes them look like they were shot by catapults or forcibly thrown out of a bar. It looks so silly!
- The encounter with Pyramid Head on the roof can become funny if you think about it. Should you try to go back through the door you entered through, rather than one of the usual "The door won't budge" messages, it says "Something's holding this door closed" which turns out to be Pyramid Head. Spooky at first blush, but together with the next thing... There's also the fence P.H. shoves you through. Ordinarily, there would be some sort of item or puzzle to remove an obstacle that's clearly removable, just as ordinarily a door you're not supposed to go through would have a busted lock or be jammed. But in this case, evidently the town realized it forgot to do that here, and sent Pyramid Head to deal with things because it was feeling lazy!
- The long bizarre elevator moment in the hospital when a hidden speaker (or possibly James's radio) plays a game show (with an audience cheering in the background) that announces James directly to play a quiz, it ask three questions for him that he'll answer in a nearby room, and laughs evilly should James answer incorrectly. The speaker finally switches off, prompting Maria to ask "What was that?!".
- And the funniest part? Maria, a manifestation and an agent created by the town to fulfil James' subconscious desires, is left completely dumbfounded by the bizzare elevator sequence, likely put in by her boss (the town) to screw with them both.
- James and Maria opens up a refrigerator lying on a floor, containing a shabby looking ring. Maria remarks that it doesn't look cute and gives it to James to hold onto, to which he sarcastically replies "Thanks".
- If you try to talk to Angela in the cemetery again, she asks "Aren't you looking for someone?" and James, who apparently forgot the reason he came here, says "That's right" and walks off.
- While normally the Lying Figures are quite creepy, shortly after you meet Maria and start walking down the road with her following you, Lying Figures will attack you by essentially catapulting themselves over the railing to land on the road. The sight of it is absurd.
- During James' first conversation with Angela we get this gem:
James: I'm lost.
James: Yeah. I'm trying to get into town?
Angela: There's one road. (beat) You, uh, can't miss it.
- Unforgettably, there's a moment in gameplay where James comes across an exceptionally nasty toilet with something stuck inside. The player is then forced to watch in horror as James, without hesitating, flinching, or rolling up his sleeve, reaches in elbow-deep to retrieve the combination to a worthless safe outside.
- When you meet Eddie in the prison, he's clearly a few pennies short of a shilling. The way James tries to pacify him sounds a lot like a parent scolding a bratty child:
- Eddie: That guy, he had it coming. I didn't do anything, he just came after me. Besides, he was making fun of me with his eyes, like that other one.
James: Just for that you killed him?
Eddie: (Getting to his feet and waving a gun around) What do you mean "just for that?"
James: Eddie, you can't just kill someone, 'cause of the way they looked at you!
- At one point, you're supposed to open a can with a can opener. Inside is...a bunch of light bulbs. Silent Hill puzzle logic is often meant to have some element of strangeness, but this one is just silly.