"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.
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 credits framed over a chiaroscuro portrait of Mira (the dog), just like the other endings feature James or Maria's shadowed face, is the icing on the cake.
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.
The weird thing is that the characters do have occupations (excluding Laura because she is a child) and defined ages. They're just not listed. For once, it's notAll in the Manual.
In James' final encounter with Eddie, he finds the latter armed with a gun, surrounded by corpses, going on a furious tirade about how he'll shoot anyone who makes fun of him. As Eddie goes to leave, what's the first thing out of James' mouth?
When traveling 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 bizarre elevator moment in the hospital where a hidden speaker hosts a game show (complete with an audience cheering in the background) and announces that James will participate in a quiz. It ask three questions that the player can later 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 fulfill James' subconscious desires, is left completely dumbfounded by the bizarre elevator sequence, likely put in by her boss (the town) to screw with them both.
James and Maria open 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."
Note his exaggeratedly macho tone when saying "thanks", as if making up for how he couldn't lift the refrigerator door without her help. It's pretty much the closest he ever gets to displaying a sense of humor.
The Great Knife can be this. It's big and really heavy, so heavy that you have to literally drag it around. Now, who else drags a giant weapon around?
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.
During James' first conversation with Angela we get this gem:
James: I'm lost. Angela:Lost? James: Yeah. I'm trying to get into town? Angela: There's one road. (Beat) You, uh, can't miss it.
The way Angela says "Lost?" makes it sound like she's never heard the word before.
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.
Even funnier: in Silent Hill 3, if you have SH2 data on your memory card, there's a moment where you can try to make the protagonist reach into the same toilet. She turns to the camera incredulously and yells at you.
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.
In a meta example, the entire justification given for this puzzle is that James has to turn on a lamp because he's incapable of finding the keyhole in the dim lighting of of the bar.
A short moment from the sub scenario Born From a Wish:
Ernest: Is it really necessary for me to answer all your tedious questions? Maria:Yes.
Should you go to the enormous bother to unlock it, the green Hyper Spray is a fine source of comedy because of how it looks like James is fighting his way through the evils of the titular town by deodorizing it, one monster at a time. See?
, complete with retro-blocky-graphics, antiquated and badly out-of-tune music, and a Catchphrase exchange. (James would return the cameo favor in both Silent Hill 3 and Silent Hill: Shattered Memories.)