Pyramid Head
http://tn3-1.deviantart.com/fs11/300W/i/2006/181/e/0/Pyramid_Head_by_jaybob.jpg
Gordon Freeman
What happens when the bad-ass nerd from Half-Life ends up in the hell world of Silent Hill?
It depends - does the Silent Hill world have any rotary saw blades lying around?
Are you kidding? Pyramid head is intended to terrify half-armed mostly defenseless individuals running for their lives already.
Gordon Freeman, on the other hand, massacred several armies just because they pissed him off. This is a man who carries around eight different weapons just so he doesn’t run out of ammunition if he has to kill 50 or 60 heavily armed and armored, expertly-trained tough-as-nails marines, with killer alien monsters and ninjas as a small snack along the way. Gordon Freeman would smack around Pyramid Head like a red-headed stepchild.
Seriously, what’s next? Master Chief from Halo versus Michael Myers? Oh Noes! Teh evil bad guy cuts at you advanced super combat armor with a… steel knife! Then you turn round and eviscerate him with a super machine gun firing .50 caliber depleted-uranium shells.
So let’s have a REAL bracket:
Master Chief vs. Lara Croft
Gordon Freeman vs. Duke Nukem
Darth Revan vs. Max Payne
The guy from “Doom” vs. the guy from “Quake”
Who’s the final four?
Even better, Master Chief vs Samus Aran.
Samus loses
Technically wasn’t Pyramid Head a manifestation of the sexual repression and guilt that the main character was feeling? So if Gordon ended up in Silent Hill, the town would probably end up cooking up something that could give him a run for his money.
Now Superman vs. Pyramid Head, I’d like to see that! 
I prefer this (warning: video) Samus vs Master Chief, wherein WE all win. 
(Although the video takes some liberties with what the characters can do and their equipment (when did Samus get a light saber/whip? Cause I totally want one in the next Metroid!))
No way. I’ve seen Halo played online; the Master Chief will get blown up by a power bomb and then call Samus a “fag” and demand that she gets kicked from the game for cheating.
She gets one in the upcoming Super Smash Brothers Brawl, although the physics aren’t fully known yet.
Konami sues Valve Corporation? Or is that the other way around? Guess it depends who makes it.
Seriously though, it’s pretty obvious what happens … the demonic denizens of Silent Hill get a thorough ass-whoopin’ like they’ve never seen. Freeman’s first-person perspective has been scientifically proven (by expendable Black Mesa NPC scientists, of course) to be 300% more effective than the cumbersome third-person perspective exclusive to the pitiful saps who wander those dark and foggy console streets.
Well, Gordon also has guns out the wazoo. Most of the protagonists in SH usually have a padded baseball bat and a B.B. Gun.
A cursed B.B. Gun…
And a very spooky, tattered picture of someone that’s dead.
[del]And a pack of cigarettes.[/del]
Master Chief gets Lara drunk and has a lot of acrobatic sex with her, then when she’s taking a skinny dip he makes off with all her weapons and skips town before she can retaliate. He could fight her honestly and win, but he’s got better things to do.
While Duke Nukem is busy checking out strippers and cracking wise about his face being on a pinball game, Gordon Freeman sneaks up and shoots him in the back of the head.
Darth Revan slaughters Max Payne by immobilizing him with a Force Whirlwind and throwing her lightsaber at his face repeatedly. It’s not the fastest method, but it’s more fun.
Doom guy and Quake guy get into a fanboy argument about which one of them is more awesome, who has the coolest weapons, etc. Then they battle inconclusively until Marcus Fenix shows up, target paints them, and they get blasted with the Hammer of Dawn orbital laser.
Now, I like VGcats, but I think the Penny Arcade interpretation is a bit more accurate. Master Chief’d be crying in the corner.
Can you say “bionic boner”?
[Fuddy Duddy Mode]
The whole point of Silent Hill is that the person trapped therein is a (mostly) normal person without superpowers (unless you happen to be a Walking Spoiler like in SH3) and a limited cache of weapons so that just about everything in the town is a threat to said person’s life and/or mental health. It’s supposed to play like a waking nightmare, where your sense of reality gets so f-ed up that even if you do get out you’re never 100% certain that you left. So therefore anybody badass going to SH would either 1) defeat the purpose of the game, or 2) create something a million times worse.
[/FDM]
That said, I would pay good money to see Solid Snake go to Silent Hill.
“Put the controller down RIGHT NOW!”
Christ, someone badass going to Silent Hill? I’d never play it. I’d get creeped out from looking at the box art.
It’d be pretty demented. Well, I hope it would be.
He can’t kill Pyramid Head, nobody can. Pyramid Head won’t go away until Gordon Freeman faces the inner guilt that brought him to Silent Hill in the first place.
Indeed. In the game, Pyramind Head was unkillable no matter the weapon used.
Of course, Gordon could just wander around moping through a nightmarish landscape until he was racked with guilt and two pyramid heads appear and off each other , but that’d be nutty…and boring. Nutty and boring.