A nostalgic showstopper from mid-20th century American kitchens, the pineapple upside-down cake is a delightful marriage of buttery caramelized fruit and tender vanilla cake. This tropical beauty gets its name from the unique method of layering fruit and sugar on the bottom of the pan, which, once baked and flipped, creates a golden, glistening crown of pineapple and cherries. Vibrant in both flavor and presentation, it's a dessert that dazzles at gatherings, recalling retro charm with every bite.
7piecespineapple ringscanned in juice, drained and patted dry
7piecesmaraschino cherrieswithout stems
For the Cake Batter:
1 ½cupsall-purpose floursifted for best texture
2teaspoonsbaking powder
¼teaspoonkosher salt
½cupunsalted butterroom temperature
1cupgranulated sugar
2largeeggsroom temperature
1teaspoonpure vanilla extractreal vanilla for best flavor
½cupwhole milkroom temperature
Instructions
Prepare the Topping:
Preheat the oven to 350°F (175°C). In a 9-inch round cake pan, add 6 tablespoons of unsalted butter and place pan in the preheating oven to melt the butter. Once melted (about 3–4 minutes), remove and swirl to coat the bottom evenly. Sprinkle 3/4 cup light brown sugar over the melted butter in an even layer.
Arrange the pineapple rings on top of the brown sugar mixture, placing one ring in the center and the others around it. Place one maraschino cherry in the center of each ring.
Make the Cake Batter:
In a mixing bowl, whisk together 1 1/2 cups all-purpose flour, 2 teaspoons baking powder, and 1/4 teaspoon kosher salt. Set aside.
In a separate bowl, cream 1/2 cup butter and 1 cup granulated sugar with an electric mixer on medium speed for 2–3 minutes, until light and fluffy. Add eggs one at a time, mixing well after each. Stir in the vanilla extract.
Alternate adding the dry flour mixture and 1/2 cup milk, starting and ending with flour. Mix until just combined, scraping down the sides as needed. Do not overmix.
Bake:
Gently spoon the batter over the arranged pineapples in the pan and spread evenly with a spatula. Bake in preheated oven for 45–50 minutes, or until a toothpick inserted into the center comes out clean and the top is golden brown.
Cool and Invert:
Allow the cake to rest in the pan for 10 minutes. Run a knife along the edges to loosen. Place a serving plate over the cake pan and carefully invert. Let gravity help release the cake before lifting the pan.
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Notes
To elevate the flavor, add 1 tablespoon of dark rum to the cake batter for a subtle tropical warmth.
For a twist, try using fresh pineapple slices that have been lightly grilled to intensify natural sugars.