Preheat oven to 325°.
Drain the pineapple and save the juice in a separate bowl. Set both aside.
Mix flour, pudding, baking powder, powdered milk, and salt in a bowl. Set aside.
In a separate bowl beat one cup of butter and sugar.
Add egg yolks one at a time until mixed, then add vanilla.
Slowly mix in the flour mixture and ½ cup of pineapple juice a little at a time until just mixed.
Stir in 2 cups of crushed pineapple. Set aside.
Take two 8 inch round pans and place a half stick of butter (¼ cup) and a tbsp of bacon grease in each. Place the pans in the oven until the butter and grease has melted and remove from oven.
Add ¾ cup of brown sugar to each pan and stir to combine and spread evenly over the bottom.
Add 1 ½ cups of crushed pineapple to each pan spread evenly.
Place pineapple rings in circle around outer edges of each pan and 1 ring in the center. Place a maraschino cherry into the center of each pineapple.
Slowly pour cake batter over the top of the pineapple rings and brown sugar mixture, making sure to evenly distribute the batter between both pans.
Bake for 45-55 minutes.
Remove from oven and let cool for 5 minutes.
Turn each cake onto a platter so that the bottom is now the top.