Baked in Cast Iron
In a 10 inch cast iron skillet, over medium heat melt the 1/4 stick butter; add the brown sugar and place the slices of pineapple on top of sugar. Saute till they begin to carmmelize; about 3-4 minutes.
Place 1-2 fresh cherries in the center of each pineapple slice and pour the rum over the top. Continue to cook for 1-2 minutes. Remove from heat and let cool for 5 minutes before adding the batter.
Add the batter to the iron skillet and bake for 30-40 minutes or until a toothpick come out clean.
Let the cake cool for 7-10 minutes before unmolding. Run a knife around the edge of the pan; place a large plate over the pan and carefully flip over the cake; let rest for 1-2 minutes until it releases.
Garnish with additional fresh cherries on top
Whip the cream in a cold bowl adding enough powdered sugar to sweeten. Add 1 teaspoon vanilla extract and serve with the cake.