Who would win?

[Cerebus]

Well it depends at which level it evolved into Raichu. If it was before 43 (on Red/Blue) then it would've missed "Thunder" which I guess is it's strongest attack. However, Pikachu still looks better than Raichu, and is still 5 levels higher, so Pikachu, yeah.

Gold/Silver vs. Ruby/Sapphire.

[Bluhman]

Raichu, because of STAB and the absence of weakness to steel-type attacks.

Krystal (Starfox) VS Heavy Weapons guy
In a sandwich eating contest

[X_marks_the_ed]

Heavy, because Krystal wouldn't enjoy it as much.

Mario Party 8 vs Mario Party 3

[Bluhman]

Mario Party 3. Because the 3rd game in a series always seems to be one of the best (Super Mario 3, Sonic the Hedgehog 3, Elder Scrolls 3, Final Fantasy 3 (the NES version isn't bad at all), Descent 3, Crash Bandicoot 3, Something else 3...)


----------------------------Pit (Kid Icarus)------------------- VS -----------------------------------------------Pit (The Void)----------------------------------------------------------

[Musha]

Pit for Kid Icarus, 'cause he's a badass angel-type dude with a freaking sword-bow(!) who actually manages to not look gay in a toga and sandals.  Pit from The Void is just some dude in a giant hamster ball.

<a href="http://io9.com/5402621/ridley-scotts-monopoly-movie-is-about-parallel-universes">Ridley Scott's Monopoly</a> vs. <a href="http://io9.com/5416779/epic-alien-battleship-movie-leaks-the-details-on-the-new-et">Peter Berg's Battleship</a>

Yes, they're both real.

[Darkfox]

Ridley Scott Monopoly, it takes either a very creative mind to make something out of that, or a lot of drugs. You make the pick.

Megaman VS Stinkoman

[Bluhman]

Stinkoman can never get powers from his enemies, no matter how many times he challenges his enemies. Megaman is much more versatile.

Megaman VS Kirby

[Darkfox]

Kirby, he could just eat Megaman, steal his power gaining ability, with his added natural ability to fly, and use all that against him.

Kirby VS Dan (Street Fighter series)

[Bluhman]

Dan, because he has no good powers to steal. Kirby swallows dan, and gains the ability to... Throw autographs. Dan can probably win if he focuses on not being stupid for the remainder.

Ice Climbers VS Pyro

[Darrellito]

Silver Surfer. Power Cosmic. Turns Cable into a cactus.

I win!

Batman (Bruce Wayne) vs. Batman (Dick Grayson)

[Cerebus]

Deadpool apparently have a tendency to break the fourth wall, therefore all this skills and schnitz is irrelevant considering he's well aware he's only a fictional character that came out of some guy's imagination, which then  means it's his creator that controls everything and decides whether he would win a fight or not. Or something. So, since he does know all this, I guess he does win.
But was it for awesomeness, he would lose hard since I always found it lame to break the fourth wall, except when it's kinda necessary.
"Press the select button."

Silent Hill vs Resident Evil.

[MissingName]

Silent hill.  You've got air raid sirens there.

Bacon vs Sausage?

[Musha]

Bacon vs Sausage?

Bacon, unless it's really good sausage.

<a href="http://www.imdb.com/title/tt1298650/">Pirates of the Caribbean 4</a> vs. <a href="http://www.imdb.com/title/tt1430132/">X-Men Origins: Wolverine 2</a>

[fruckert]

I'd take Pirates over Origins any day.
Even though 2 & 3 were a little too...dumb.

The Diabeetus Guy (can't remember his name) vs. Vince Offer.

[Darkfox]

Diabeetus

Rick Astley VS Weegee