In the red corner from New York City, New York. Weighing in at....well a lot. He is the iron fisted ruler of much of the criminal underworld of the East Coast and beyong. Ladies and Gentleman I give you Wilson Fisk...I give you THE KINGPIN!!!
Homeworld: Marvel Universe
Powers: Peak human strength and fighting skills. Trained as a sumo and wrestler. Carries a trick cane that fires gas and occasionally lazers. Kingpin is a ruthless and agressive fighter who routinely walks away from fights with Daredevil, Punisher, and Spider Man. His immense strength is enough to let him crush a mans bones with ease.
Now, in the blue corner from Vice City, Florida. Wieghing in at...a lot less than Kingpin. He is the undisputed ruler of Vice Cities criminal under ground. His bloody rampages have left thousands dead. Capable of boosting any car in mere seconds he is the master of every type of fire arm known to man. Ladies and Gentlemen I give you the King of Cool, Tommy Vercetti!!!!
Homeworld: Grand Theft Auto Vice City.
Powers: Master any type of vehicle and fire arm imagineable. Also good with close combat weapons like chainsaws, ball bats, etc. Tommy has more guns than the friggin Punisher and can always drive a speeding vehicle into an enemy if need be. Capable of firing rockets from helicopters or pretending to be a cop Tommy ammasses a huge body count simply by driving down the street.
Now I propose that this fight allow both men to bring whatever they want to bear. Tommy can come in guns blazing if he wants and Kingpin can throw a few random goons at him as well. No matter how much damage gets done their lawyers will keep them out of jail so the skies the limit. I'll note that Tommies guns give him a bit of an advantage but then again how many times has the friggin Punisher tried to kill Kingpin and yet ole fat boy still lives right? Should be an even fight.