Combine the cake mix, Kool-Aid, oil, and eggs in a large mixing bowl and mix well.
Pour the mixture into greased cupcake wrappers until about the half way mark. Continue for all 24 cupcakes.
Bake for about 18-20 minutes or until poked with a toothpick, the toothpick comes out clean.
While they are cooling prepare the whipped cream. Place the whipping cream, powdered sugar, and vanilla in a mixing bowl and mix on high until a whipped consistency is formed.
Decorate the cupcakes with the whipped cream and top with a cherry.