Step 1

Preheat the oven to 375 degrees and center rack in the oven. I used only one 9-inch skillet to make both cakes by doing one at a time. Simply wipe out your skillet after removing the cake and start over. If you have 2 skillets, even better, make them both at the same time by staggering the pans in the oven.

Step 2

Prepare the topping first by placing 1/4 cup butter in cast iron skillet. Place skillet in the oven until the butter has melted, this only takes a few minutes.

Step 3

Remove skillet from the oven and sprinkle 1 cup of light brown sugar over the butter. Drain pineapple rings, reserving the juice to store any leftovers.

Step 4

Gently place pineapple rings onto the brown sugar in the skillet. Place a cherry in the middle of each of the pineapple rings.

Step 5

Prepare the cake batter by combining all batter ingredients in a mixer bowl. Mix at low speed for 30 seconds or so to incorporate, then increase speed to medium and mix for 5 minutes, occasionally scraping bowl if needed.

Step 6

Separate the batter evenly between two bowls. Do not be concerned if there are some small butter bits still in the batter, it will still bake up beautifully!

Step 7

Carefully, but fairly quickly, pour the batter over the pineapples. You want to pour the batter on top, moving around as you go, so that you don't move any of the pieces of fruit around.

Step 8

Bake 30 minutes. The sides should be bubbly and the top will be browned. Cool for 10 minutes on a wire rack.

Step 9

Place flat cake plate over the skillet, then using oven mitts, invert the pan onto the plate. If necessary, use an icing spatula to scoop up any topping left in the pie to patch any bare spots on top of the cake.

Step 10

The instructions are basically the same using standard 9" round cake pans or a 13" x 9" baking pan. For a 13" x 9" baking pan, form pineapple flowers all over the cake, you should be able to fit about 8 or more flowers. Bake the 13" x 9" pan for 35-40 minutes. You may need to loosen the cake from the sides of the pan before inverting. For round cake pans, follow baking times for skillet above.