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Writer's pictureMangia McCann

Turn your life upside down with this Pineapple Upside Down Cake!

You know what today is? No, not that! Put down the bong, and pick up a pineapple! It’s Pineapple Upside Down Cake Day; not to be confused with upside down face day. I’ve always seen these cakes and they reminded me of a more carefree time: the 60’s - where everyone got a house in the ‘burbs, picnics and block parties were abundant, everyone danced and listened to the same music, dads were svelte wearing their Ray-Bans, moms were all hotties in sun dresses, and maybe that day was the day you’d have your face melted off by a Russian nuke…yes, simpler times indeed!


Anyway, I never had made this cake until last night, and much like wistful memories of the past, there’s always an underlying factor which makes you grateful that we’ve moved on in life. The recipe was from Cook’s Country and the cake itself is great, but the topping is unbalanced on the palate and combined with the lightly sweet cake, as a whole, is inharmoniously, and cloyingly, sweet. Too much for my palate. Also, they have you cook the caramel for too long, so the end result looks much darker than their photo, which I attempt to account for in my adaptation. So, if you have an extreme sugar tooth, below is the recipe.

Pineapple Upside Down Cake adapted from Cook’s Country

Note: most pineapple at the store, like most produce, are under ripe when you purchase them. Pick out the best looking pineapple with the freshest leaves as these are the most healthy of the bunch, Place the pineapple on your counter and allow to fully ripen for about 5-10 days. The exterior background color will turn golden (from green) and the pineapple will give slightly when you give a gentle squeeze when fully ripe.

  • Pineapple

  • 1.5 cups brown sugar

  • Pineapple juice

  • Maraschino cherries, stemmed

  • 2.5 sticks of butter

  • 2 tbsp dark rum

  • 1.5 cups AP flour

  • 1 tsp baking powder

  • 1 cup sugar

  • ½ cup whole milk

  • 2 eggs

  • 1 tsp vanilla extract

  • Other: Biscuit/cookie rounds, 9” cake pan, parchment paper

Slice the top and bottom off of the pineapple, then slice off the exterior until you have about a 4” diameter pineapple. Slice the pineapple ½ thick. Using a 3.25” round, press down on the slices and remove the excess. Then, using a 1.25” round, press down in the center of each pineapple slice to remove the core.


Using a rubber-coated whisk, combine the brown sugar and 1 cup of pineapple juice in a large non-stick skillet, over medium heat. Once combined, place 8 rings into the skillet and add the pineapple rings. Sauté for about 8 minutes, flipping halfway through.


Meanwhile, preheat the oven to 350 degrees with the rack in the middle. Spray the cake pan with baking spray. Place a ~9-inch round of parchment paper on the bottom of the pan and spray the paper. Portion out 1.5 sticks of butter into tbsp-size slices and reserve.


When the pineapples have cooked, remove them from the caramel and place 7 or 8 of the rings into the bottom of the prepared cake pan. Place the first directly in the middle and surround with the remaining rings. When the pineapple rings are set in the pan, place cherries into the center of each slice.


Return the caramel to the heat, when starting to bubble, add in the sliced butter and whisk until melted and incorporated. Continue cooking until the mixture has reached 260 degrees, remove from the heat and let cool for a few minutes. Then, pour ¾ cup of the caramel into a measuring cup. Drizzle the ¾ cup over the prepared pineapple rings.


In the caramel skillet, whisk in the rum and 2 tbsp pineapple juice until combined. Reserve. In a small pot melt the remaining stick of butter. Reserve.


In a small bowl, briefly whisk the flour, baking powder, and a ½ tsp of salt. In a large bowl, combine the sugar, milk, eggs, and vanilla and whisk until fully incorporated, about a minute. Whisk in the melted butter. Then whisk the flour into the egg/sugar mixture until no more dry flour remains. Pour the batter into the cake pan.


Bake the cake for about 40-45 minutes until a toothpick comes out clean. Place the cake pan on a cooling rack and run a paring knife around the edge. Using two toothpicks, poke about 80 holes all over the cake. Briefly reheat the caramel in the pan and brush ½ cup of the caramel over the cake.


Let the cake cool for 30 minutes. Place your serving platter over the pan and swiftly, but carefully, flip everything upside down. Gently remove the parchment from the cake and serve, passing along extra sauce, if desired.

______________________________ Copyright 2022, Brendan McCann, All Rights Reserved.


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