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Pineapple Upside-Down Cheesecake Recipe

4.7 from 137 reviews

This Pineapple Upside-Down Cheesecake combines the tropical sweetness of pineapple rings and maraschino cherries with a creamy, smooth cheesecake filling on a buttery graham cracker crust. Baked in a water bath to ensure a silky texture, this dessert offers a delightful twist on classic pineapple upside-down cake with luscious cheesecake layers.

Ingredients

Scale

Crust & Topping

  • 1/2 cup brown sugar
  • 6 to 8 pineapple rings, canned or fresh
  • 6 to 8 maraschino cherries
  • 1/4 cup unsalted butter, melted
  • 1 1/2 cups graham cracker crumbs
  • Additional 1/4 cup unsalted butter, melted (for crust mixing)

Cheesecake Filling

  • 24 ounces cream cheese, softened
  • 3/4 cup granulated sugar
  • 1/2 cup sour cream
  • 1 teaspoon vanilla extract
  • 3 large eggs

Instructions

  1. Prepare the Base and Fruit Layer: Preheat oven to 325°F (163°C). Grease a springform pan thoroughly, then evenly sprinkle the brown sugar on the bottom. Arrange the pineapple rings on top of the sugar, placing a maraschino cherry in the center of each ring. Drizzle the melted butter over the pineapple and cherries to help caramelize the topping during baking.
  2. Make the Crust: In a bowl, mix the graham cracker crumbs with the remaining melted butter until crumbs are evenly coated. Press this mixture firmly over the pineapple layer in the pan to form the crust. Place the pan in the freezer for 10 to 15 minutes to help the crust set before baking.
  3. Prepare Cheesecake Batter: In a large mixing bowl, beat the softened cream cheese with granulated sugar until the mixture is smooth and free of lumps. Add the eggs one at a time, mixing slowly after each addition to prevent overbeating, which can cause cracks.
  4. Add Sour Cream and Flavoring: Stir in the sour cream and vanilla extract into the cream cheese mixture, blending thoroughly until the batter is smooth and creamy without any streaks.
  5. Assemble and Smooth Batter: Pour the cheesecake filling evenly over the chilled crust and pineapple layer. Use a spatula to smooth the top for an even surface.
  6. Bake in a Water Bath: Place the springform pan into a larger baking dish or roasting pan. Fill the outer pan with hot water halfway up the sides of the springform to create a water bath (bain-marie). Bake in the preheated oven for 60 to 70 minutes, until the center is mostly set but still slightly jiggly.
  7. Cool Gradually: Turn off the oven and crack the oven door open. Let the cheesecake cool inside the oven for 1 hour. This gradual cooling helps prevent cracks and preserves the creamy texture.
  8. Chill Thoroughly: Remove the cheesecake from the oven and water bath. Refrigerate for at least 4 hours or preferably overnight to allow the cheesecake to fully set and flavors to meld.
  9. Unmold and Serve: After chilling, carefully run a knife around the edge of the pan to loosen the cheesecake. Release and remove the springform sides. Invert the cheesecake onto a serving plate so that the pineapple and cherry topping is displayed beautifully on top. Slice and serve chilled.

Notes

  • Use a clean kitchen towel to cover the outside of the springform pan when placing in the water bath to prevent water from leaking in.
  • If using fresh pineapple, ensure it is well-drained to avoid excess moisture in the cake.
  • Do not overbeat the eggs into the cream cheese mixture to avoid cracking during baking.
  • Letting the cheesecake cool gradually in the oven helps prevent the top from cracking.
  • Allow the cheesecake to chill overnight for the best texture and flavor.
  • You can garnish with extra maraschino cherries or pineapple slices before serving if desired.

Keywords: pineapple upside-down cheesecake, pineapple cheesecake, upside-down cake, creamy cheesecake, tropical dessert, pineapple dessert, graham cracker crust cheesecake