Though gaming in the 21st century has its share of icons, they never got the treatment that video game characters from the 90's did. If Nathan Drake, Master Chief, and the Weighted Companion Cube had been around a decade ago, surely they would be strapping on their driving gloves and getting ready to go for the gold in a wacky kart-racing game.
Sense of Wonder: Both games are published by Nintendo, so a sense of childlike wonder is a must. As fun and varied as Mario Kart 64's visuals could be, with its Chocolate Mountains and its Kalimari Desserts, Diddy Kong blows Mario out of the water on this one (probably whilst on his hovercraft). The racing in DKR is adequate, but the atmosphere was the real reason we looked so fondly upon the game in the first place. Who doesn't remember thinking "holy crap" when they first saw that you could race with a plane in this game? A PLANE! Just seeing that world map and hearing the sound of Tiptup's throaty yell makes me go all nostalgic.
Winner: Diddy Kong Racing