I started making my special pineapple cake about 15 yrs ago. My father loved it at first bite and would often call and ask me to bake one for him. I would drop everything and bake it and he would come over to pick it up but first he sat down and had to eat about half of it right then. Now I my brother calls and ask for it. The difference is in the icing I make. I have made a scratch cake recipe for it now but it can be made with a box cake mix just as well. The big secret in the cake itself is to be sure to poke holes in the layers and add the juice from the pineapple.
Cream the butter and sugar together until fluffy stir and scrap off sides and bottom of bowl making sure it is well mixed and sugar is not grainy. about 10 min. I sift my sugar
Add the eggs one at a time to the cream mixture and beat together until blended
Sift the cake flour, salt,pudding mix and baking powder together then slowly add a little flour mix at a time alternating with the milk. You can mix the vanilla in the milk before adding milk to the cake mixture. Beat mixture until smooth.
In two 9inch cake pans, spray with baking spray and add the mixture. Beat the pans on counter to be sure the mix is level
Pre Heat oven to 350
Place the cakes in the oven on middle rack and bake about 35 minutes or until tooth pick inserted in the middle comes out clean. Remove from oven and wait 10 minutes before turning out on cooling racks
Place cream cheese in large mixing bowl and add 1Tlbs of pineapple juice to it and whip with a hand mixer. Stir in the cool whip and fully mix.
Over a mixing bowl drain the 2 cans of crushed pineapple squeezing as much juice out as possible you should have about 2 cups of juice. Mix the juice with the 4 Tlbs of sugar. In another bowl empty the pineapple and add 2 Tlbs of sugar to it
Place first layer on cake plate and poke holes in it lightly. Slowly drizzle 1 cup of sweetened pineapple juice over it. Allow time to stand so it will soak in. Spread some icing over the layer then place about 1 cup of pineapple on the layer. Place second cake layer on top of this layer and poke some holes all over it lightly. Drizzle the remaing pineapple juice over this layer slowly allowing to soak in a little at a time. This is time consuming but don't get in a hurry or your cake will be dry and not full of the pineapple flavor. Spread icing over the top layer and around the sides. Take rest of the pineapple and crumble over the top and sides press in lightly. The longer this cake rest the more moist it will be. Cover in a tight cake keeper and refrigerate.