FROM: Tony Hawk series/Zork series

>>You are standing in a large cave lit by torches. Amidst the flickering shadows, you can glimpse exposed veins of gold in the walls and ceiling. You hear the babbling of an underwater river nearby. There are exits to the NORTH and EAST. A TONY HAWK is here, guarding a CHEST.
>KILL TONY HAWK
>>What will you kill the TONY with?
>KILL TONY HAWK WITH FIRE
>>You do not have a FIRE.
>PUNCH TONY HAWK
>>The TONY laughs at your feeble efforts and does a BITCHIN' KICKFLIP.
>THIS GAME SUCKS
>>Can you please repeat that?
>EXIT
>>Tony Hawk wins.

FROM: Sonic the Hedgehog series/Superman 64

Instead of resorting to violence, the two heroes decide to try and talk through their differences. They bond over their shared love of rings and decades of shitty games, instantly become best friends and agree to walk out of the competition. Twenty years later, they have a major falling out over a restaurant bill. Sonic... wins?

FROM: Lego Indiana Jones: The Original Adventures/Devil May Cry series

Dante crashes dramatically through a domed skylight, plunging toward Lego Indy while executing wicked-cool sword tricks and scissor kicks. As he finishes his descent, he brings his sword crashing down on Indy's head, shattering him into a dozen chunks of sharp, jagged plastic. One of those chunks is sent flying down Dante's throat by the brutal force of the attack, and Dante slowly chokes to death as Indy reappears, one life down but otherwise unharmed. Lego Indy wins.

FROM: Street Fighter Alpha series/Final Fantasy VII

An epic battle rages between Dan and Aerith for days until Dan, battered and exhausted, realizes that Aerith has been dead the whole time. In fact, she's been dead for 11 years, because SEPHIROTH KILLED HER. Dan writes it off as a training mode. Dan wins.

FROM: Grand Theft Auto IV/Pokémon series

The fight starts off in a blaze of bullets and pyrotechnics, and within minutes, the two combatants are locked into a Mexican standoff. Niko's pistol is pressed hard against Charizard's forehead. Charizard's fire-breathing mouth is wide open and leveled menacingly at Niko. Just then, Niko's cell phone rings.
"COUSIN! It is an emergency! You need to drop whatever you are doing and come with me to see some EMERGENCY TEEEEEEEEEEEEEEEEEEEEEEEEEEEEETEEEEEEEEEEEEEEEEES!"

“Roman, I don’t have ti-“ FWOOOOOSH. Charizard wins.

FROM: Resident Evil/Super Monkey Ball series

Barry mutters something stiff and moronic along the lines of "hope this is not an unlocking sandwich" before taking aim with his oversized revolver. AiAi immediately tilts the battlefield, and Barry is sent tumbling into space through a line of floating bananas. AiAi wins. Right? Fine. Yes? YES! NEXT!

FROM: Mike Tyson's Punch-Out!!/God of War series

Kratos capitalizes on Tyson’s inability to turn around and grabs him from behind, initiating a quicktime event. However, after pushing X when he was supposed to press Circle, Kratos is immediately disqualified. Tyson wins.

FROM: Leisure Suit Larry series/Pong

After being locked in a room for hours with the Pong paddle, Larry is driven to madness by the paddle’s constant “booping.” But the final straw comes later, when the two hit a bar and the paddle gets laid while Larry comically strikes out, over and over again. The night out becomes the basis for Leisure Suit Larry 8: Cripes, a Pong Paddle Even?

Despairing at the joke his life has become, Larry throws himself under the wheels of a passing bus. The paddle wins.

FROM: Soulcalibur IV/Bioshock

Yeah, we know what you're thinking: Vader's awesome Force powers and lightsaber mastery will absolutely cream the big, slow, stupid Big Daddy. But this is the Darth Vader from Soulcalibur IV, meaning people with metal weapons are actually a decent challenge for him. Vader takes a swing at Big Daddy, but his lightsaber clangs uselessly against the armored behemoth's metal shell. Big Daddy’s eyes turn red and, roaring, it kills Vader. In a funny way. It was really funny, but you pretty much had to be there. Oh man, it was hilarious.

FROM: Metal Gear series/Disgaea

Etna looks around, confused. She was almost certain she saw someone enter the arena with her, but there's nobody in sight. Meanwhile, Snake crouches only a few feet away under a cardboard box, ready to leap up and snap Etna's tiny neck the second she wanders too close. Suddenly, Snake's codec rings.
 
“NIKO, LET'S GO LOOK AT SOME TEEEEEEEEEET- WAIT, WHAT NUMBER DID I DIAAEL?”
“Uh… 140.86.”

Etna whirls around and boots the box right off of Snake, then leaps back and hurls a Prinny penguin-bomb-thing at him. Unprepared to handle both a bomb and a phone call, Snake dies. Somewhere, a fat Eastern European man screams, "Snake!? SNAAAAAAAKE! TEEEEEETEEEEES!" Etna wins.

FROM: Call of Duty 4/Pac-Man series

Carefully creeping up on Pac-Man during a rainstorm on the deck of a tanker, Soap edges out from behind the protective cover of a shipping container and squeezes off a silenced burst in Pac-Man's direction. However, the bullets are useless against Pac-Man, who simply chews his way along them like a string of power pellets.

The bullets' flight path leads Pac-Man directly to Soap's hiding place - but luckily for Soap, he's found a better one nearby. As Pac-Man wakka-wakkas past, Soap slips out of the shadows and draws his knife across Pac-Man’s throat. Except Pac-Man doesn’t have a throat. Pac-Man devours Soap. Pac-Man wins. Pac-Man.