Heat oven to 350°F. Spray a 9 x 13-inch baking dish with cooking spray and set aside.
In a large mixing bowl, combine cake mix, eggs, oil, and crushed pineapple with juice with a hand mixer until well combined. Pour into prepared pan.
Bake for 25-30 minutes or until a wooden pick inserted in center of cakes comes out clean.
Allow the cake to cool completely on a wire rack.
In a medium-size mixing bowl, fold together whipped topping, vanilla pudding, and 1 can crushed pineapple with the juice. Spread the icing mixture over the top of the cooled cake.
Store in the refrigerator.
Just before serving, top each square with a cherry, if desired.