The Pineapple Upside-Down Cake is a nostalgic dessert that tells a story of simplicity, creativity, and the beauty of transforming humble ingredients into something extraordinary. Its history dates back to the early to mid-20th century, a time when canned goods became popular in American households. Canned pineapple, affordable and convenient, played a pivotal role in the invention of this delectable cake. Combined with maraschino cherries for vivid pops of color and paired with a rich, buttery cake, this dessert became an instant classic.
While inverted cakes—the technique of baking a topping at the bottom of the pan and flipping it out after baking—had been around for centuries, the Pineapple Upside-Down Cake owes much of its widespread fame to the Dole Pineapple Company. In the 1920s, Dole held a recipe contest to promote their canned pineapple, and nearly 60,000 entrants submitted versions of pineapple-themed desserts. The upside-down cake quickly stood out for its visual appeal and irresistible blend of caramelized fruit with a moist and buttery cake. Its bright and tropical appearance, featuring golden pineapple rings and cheerful maraschino cherries, embodied the optimism and creativity of the era.
Over time, the Pineapple Upside-Down Cake became a retro dessert staple, gracing tables during family gatherings, holiday celebrations, potlucks, and church socials. Its craftsmanship was admired not only for its beauty but also for its simplicity—a dessert that anyone could successfully bake with basic pantry staples and canned goods. The original recipes, often baked in cast-iron skillets, produced a dense and sugary treat that retained its charm long into modern times.
This particular recipe seeks to preserve the comforting nostalgia of the classic version while introducing subtle enhancements for today’s bakers. By balancing the buttery, caramelized topping with a light, airy cake base, it brings a refreshed texture to the dessert while maintaining its beloved flavors. The use of fresh or high-quality canned pineapples and the option to add a dash of rum extract or a sprinkle of cinnamon offer a contemporary twist for those looking to personalize their cake.
Beyond its delicious taste, this cake carries an aura of celebration. Its dramatic reveal when flipped out of the pan mirrors the joy it brings to those who eat it. Few desserts manage to blend nostalgia, flavor, and presentation as seamlessly as the Pineapple Upside-Down Cake. It bridges generations over shared memories of childhood dessert tables and family dinners.
Whether you’re a seasoned baker or someone exploring this dessert for the first time, Pineapple Upside-Down Cake is a testament to the idea that simple ingredients can yield extraordinary results. From its caramelized topping to its signature retro charm, this delightful dessert is a guaranteed centerpiece for any occasion—or even an ordinary weekday indulgence. When you bake and invert it, you’re also turning over a piece of culinary history, keeping alive a recipe that has charmed home bakers for nearly a century.
Pineapple Upside-Down Cake
Ingredients
For the topping
- ½ cup unsalted butter melted
- 1 cup light brown sugar packed
- 7 slices pineapple rings canned or fresh
- 7 pieces maraschino cherries
For the cake
- 1 and ¾ cups all-purpose flour
- 2 tsp baking powder
- ¼ tsp salt
- ½ cup unsalted butter softened
- 1 cup granulated sugar
- 2 large eggs room temperature
- 1 tsp vanilla extract
- 1 and ¼ cups whole milk room temperature
Instructions
- Preheat the oven: Begin by preheating your oven to 180°C (350°F). Prepare a 9-inch round cake pan by generously buttering the sides.
- Make the topping: Pour the melted butter into the bottom of the prepared cake pan, swirling to evenly coat the base. Sprinkle the brown sugar evenly across the melted butter, then arrange the pineapple slices in a single layer over the sugar. Place a maraschino cherry in the center of each pineapple ring.
- Prepare the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, about 3 minutes. Beat in the eggs one at a time, ensuring each is fully incorporated before adding the next. Stir in the vanilla extract.
- Combine dry and wet ingredients: Gradually add the dry ingredients to the creamed mixture, alternating with the milk. Start and end with the flour. Mix until just combined, being careful not to overmix.
- Assemble and bake: Pour the batter over the arranged pineapple and cherries, smoothing the top with a spatula. Bake in the preheated oven for 45-50 minutes, or until a toothpick inserted into the center comes out clean. The top should be golden brown with a slightly springy texture.
- Cool and serve: Allow the cake to cool in the pan on a wire rack for about 10 minutes before carefully inverting it onto a serving platter. Let it cool completely or serve slightly warm.
