I’ll always associate this cake with my sister who has been an avid baker since her Easy Bake Oven days. Remember those? She quickly graduated and began baking in the big oven. A simple version of this cake was one of her first cakes and grandma’s favorite. Adding spiced rum enhances the tropical flavors and makes this an adult version of a childhood favorite.
Coat the sides with a little brown sugar.
Since I’m using a boxed cake mix, I took another short cut and used a non-stick baking spray on my 9 X 3 round cake pan. Drain and reserve the juice from the cans and sprinkle the pineapple slices with some spiced rum. Melt the butter in a sauce pan and pour it in the baking pan. Evenly sprinkle the brown sugar, layer the pineapple slices in a single layer and fill in the gaps with cherries.
The cake comes out golden and moist. 
Such a pretty presentation.
In a separate bowl, prepare the cake mix as directed, but substitute the reserved pineapple juice and some rum for the liquid amount the box requires. Add the vanilla and mix all the cake mix ingredients. Pour the batter into the pan and bake it at 350°F for 50 – 55 minutes or until a toothpick comes out clean. Note: If you’re using a different size pan, you’ll need to adjust the cooking time. The box will provide various suggestions.
While the cake bakes, make the simple syrup and add a few tablespoons of rum. When the cake is out, use a skewer to poke holes in the cake and pour the rum simple syrup evenly over the cake. Allow it to all soak in for 10 minutes before inverting.
The cake is absolutely moist and delicious! I love the warm spice hints of the flavored rum and the caramelized tropical pineapple slices. It’s just delightful. Bring back an old classic for your family and sit back and enjoy the smiles!
Drunken Pineapple Upside-Down Cake
This is an adult version of a childhood favorite cake.
Ingredients
- ½ cup butter, unsalted (1 stick)
- 1 cup brown sugar, packed
- 2 8 oz. can of sliced pineapple, drained, reserve juice
- 13 maraschino cherries
- 1 yellow cake mix, prepared as directed
- 1 tsp vanilla extract
- Captain Morgan Spiced Rum
- ½ cup simple syrup (granulated sugar and water)
Instructions
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Preheat oven to 350° and grease a 9 X 3 inch round pan.
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Placed drained pineapple rings in a small bowl and drizzle with spiced rum. Set aside.
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Melt the butter in a sauce pan over medium heat. Pour into your prepared 9 X 3 round pan. Sprinkle brown sugar evenly to cover the butter and coat the sides of the pan. Arrange a single layer of pineapple rings and place a maraschino cherry in the center and gaps.
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In a separate mixing bowl, prepare the cake mix as directed, substituting reserved pineapple juice and spiced rum for the water liquid measurement in the directions. Add vanilla extract and mix all ingredients to combine.
Note: The reserved pineapple juice alone will not meet the cake mix liquid required amount. Measured out the pineapple juice, use rum to make up the difference.
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Pour the cake batter into the pan and spread evenly. Tap a few time to release any air bubbles. Bake at 350° for 50 – 55 minutes or until you insert a toothpick in the center and it comes out clean. Remove from the oven and place on baking rack.
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Make the simple syrup while cake bakes. Add equal parts of white granulated sugar and water to a sauce pan. Cook over medium heat until sugar dissolved and it begins to bubble. Remove from heat and add two tablespoons of spiced rum to the syrup. Stir and set aside to cool until the cake is ready.
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Using a wooden skewer, poke holes into the cake and pour the rum-simple syrup mixture evenly over the cake. Allow 10-15 minutes to soak in prior to inverting the cake.
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After 15 minutes, invert the cake onto a serving platter.
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Note: Some pineapples and cherries may stick to the pan. Carefully remove them and place them on the cake.
