Pineapple Upside-Down Cheesecake: A Tropical, Tangy, Creamy Dream

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Sure! Here’s a full, detailed, and rich recipe for Pineapple Upside-Down Cheesecake—from its origin story, to a full breakdown of ingredients, steps, and even a shoutout to dessert lovers. Let’s dive in!

Pineapple Upside-Down Cheesecake: A Tropical, Tangy, Creamy Dream

Introduction:

Pineapple Upside-Down Cheesecake is a stunning fusion of two beloved desserts—Pineapple Upside-Down Cake and classic New York-style cheesecake. With its caramelized brown sugar-glazed pineapple topping, rich creamy cheesecake center, and soft buttery cake base, this dessert is a showstopper at any gathering. Whether you’re celebrating a birthday, holiday, or simply your love of tropical sweets, this recipe delivers both elegance and indulgence.

A Brief History:

The upside-down cake gained popularity in the U.S. in the early 20th century, particularly after canned pineapple became widely available. It became iconic in the 1920s after Dole hosted a recipe contest, receiving over 2,500 submissions for pineapple upside-down cake. Cheesecake, meanwhile, dates back to ancient Greece, but the creamy version we know today flourished in New York. Combining both is a modern twist that blends old-school charm with decadent flavor.

Ingredients:

For the Pineapple Topping:

  • 5 tablespoons melted unsalted butter
  • 2 tablespoons brown sugar
  • 2 cans (8 ounces each) pineapple slices, drained
  • Maraschino cherries (optional but classic)

For the Cheesecake Layer:

  • 2 (8 oz) blocks of cream cheese, softened
  • ¾ cup granulated sugar
  • 2 teaspoons vanilla extract
  • 3 whole eggs
  • ¼ cup sour cream
  • 2 tablespoons all-purpose flour

For the Cake Layer:

  • 1 cup all-purpose flour
  • ½ cup granulated sugar
  • 1 teaspoon baking powder
  • ¼ teaspoon baking soda
  • ¼ teaspoon salt
  • 1 large egg
  • ½ cup milk
  • ¼ cup vegetable oil
  • 1 teaspoon vanilla extract

Instructions:

Step 1: Prepare the Pan & Topping

  1. Preheat your oven to 325°F (160°C).
  2. In a 9-inch springform pan, pour the melted butter and sprinkle the brown sugar evenly.
  3. Arrange the pineapple rings on top of the sugar. Place a maraschino cherry in the center of each ring if you like. Set aside.

Step 2: Make the Cheesecake Layer

  1. In a large bowl, beat the cream cheese until smooth.
  2. Add in the sugar and mix until fluffy.
  3. Beat in eggs one at a time. Add sour cream, flour, and vanilla extract. Mix until just combined.
  4. Gently pour the cheesecake mixture over the pineapple in the pan. Smooth the top.

Step 3: Bake the Cheesecake

  1. Wrap the bottom of the springform pan with foil and place it in a larger baking dish.
  2. Fill the outer pan with 1 inch of hot water (this is your water bath).
  3. Bake for 50–60 minutes or until the center is set but still slightly jiggly.
  4. Turn off the oven, crack the door, and let it cool in the oven for 1 hour.
  5. Remove from water bath and chill in the fridge for at least 4 hours (or overnight).

Step 4: Prepare the Cake Layer

  1. In a bowl, whisk together flour, sugar, baking powder, baking soda, and salt.
  2. In another bowl, mix egg, milk, oil, and vanilla.
  3. Combine wet and dry ingredients. Mix until just combined.
  4. Pour into a greased 9-inch round cake pan and bake at 350°F (175°C) for 25–30 minutes or until a toothpick comes out clean.
  5. Let it cool completely.

Step 5: Assemble the Cheesecake

  1. Carefully remove the cheesecake from the springform pan.
  2. Place the cake layer on a serving plate.
  3. Gently place the cheesecake on top of the cake layer with pineapple side facing up.

Conclusion:

The result? A beautifully layered dessert that looks impressive, tastes heavenly, and balances tropical fruit, caramel, and velvety cheesecake in each bite. It’s a dessert that has the nostalgic warmth of Grandma’s kitchen and the flair of a modern patisserie.

For the Dessert Lovers:

To all cheesecake connoisseurs and pineapple fans—this one’s for you. Whether you’re enjoying a slice by the beach or bringing a surprise to a potluck, Pineapple Upside-Down Cheesecake is love on a plate. Serve it chilled, share it warm, or keep it all to yourself (no judgment here).

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