In Donkey Kong Country, Donkey Kong hires Diddy to guard his banana horde from people who might want to steal it. Overhearing this, King K. Rool sends an attack on Diddy, who is beat up and tossed in a barrel and thrown into the bushes. Donkey Kong soon finds and frees him, and the two set out on an adventure to get the bananas back. In the game, Diddy Kong was used either for two player mode, or as a sort of level continue. As long as either Donkey Kong or Diddy Kong were alive, a life was not lost. The missing teammate could then be retrieved by breaking open a barrel with the letters DK on it, similar to the one Diddy was initially trapped in.
Since his debut, he has appeared in many games, ranging from those in the Donkey Kong universe, like Donkey Kong Barrel Blast, to those in the expanded Mario universe, such as Mario Kart: Double Dash!! and Mario Strikers Charged.