Pineapple Right Side Up Cheesecake


Experience a taste of tropical paradise with our irresistible pineapple upside-down cheesecake. Combining the classic flavors of a pineapple upside-down cake with the creamy richness of cheesecake, this decadent dessert is sure to transport your taste buds to sun-drenched shores and swaying palm trees. Join us as we delve into the delicious world of this delightful dessert and discover why it’s the perfect sweet treat for any occasion.

The Allure of Pineapple Upside-Down Cheesecake: Pineapple upside-down cheesecake is a delightful fusion of two beloved desserts that come together to create a culinary masterpiece. The caramelized pineapple slices, gooey brown sugar glaze, and maraschino cherries of a traditional pineapple upside-down cake perfectly complement the creamy smoothness of a classic cheesecake. The result is a dessert that’s both familiar and exciting, with layers of flavor and texture that will leave you craving more.

Recipe: Ingredients:

For the Pineapple Upside-Down Topping:

  • 1/4 cup unsalted butter
  • 1/2 cup packed brown sugar
  • 1 can (20 ounces) pineapple slices, drained
  • Maraschino cherries, for garnish

For the Cheesecake Filling:

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

For the Crust:

  • 1 1/2 cups graham cracker crumbs
  • 1/4 cup granulated sugar
  • 1/2 cup unsalted butter, melted


  1. Prepare the Crust: In a mixing bowl, combine graham cracker crumbs, sugar, and melted butter. Press the mixture into the bottom of a 9-inch springform pan. Chill in the refrigerator while preparing the topping and filling.
  2. Make the Pineapple Upside-Down Topping: In a saucepan, melt the butter over medium heat. Stir in the brown sugar until dissolved and bubbling. Pour the mixture into the bottom of the prepared springform pan. Arrange pineapple slices over the brown sugar mixture, and place maraschino cherries in the centers of the pineapple slices. Set aside.
  3. Prepare the Cheesecake Filling: In a large mixing bowl, beat the cream cheese and sugar until smooth and creamy. Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract and sour cream until combined.
  4. Assemble the Cheesecake: Pour the cheesecake filling over the pineapple upside-down topping in the springform pan, spreading it evenly with a spatula.
  5. Bake the Cheesecake: Place the springform pan on a baking sheet to catch any drips. Bake in a preheated oven at 325°F (160°C) for 55-60 minutes, or until the center is set and the edges are lightly golden.
  6. Cool and Chill: Allow the cheesecake to cool completely in the pan on a wire rack. Once cooled, refrigerate the cheesecake for at least 4 hours, or preferably overnight, to firm up before serving.
  7. Serve and Enjoy: To serve, carefully remove the sides of the springform pan. Slice the cheesecake and serve chilled, with the pineapple upside-down topping facing up. Enjoy the tropical flavors and creamy richness of this delightful dessert!

Health Benefits: While pineapple upside-down cheesecake is undeniably indulgent, it offers a few health benefits thanks to its main ingredient, pineapple. Pineapple is rich in vitamin C, bromelain, and antioxidants, which can support digestion, boost immunity, and reduce inflammation.

Serving and Storage Tips:


  1. Chilled Delight: Serve pineapple upside-down cheesecake chilled for the best taste and texture. The creamy richness of the cheesecake and the caramelized pineapple topping are at their most delicious when served cold.
  2. Garnish with Freshness: Before serving, consider garnishing each slice with a dollop of whipped cream and a maraschino cherry for an extra touch of sweetness and visual appeal. Fresh mint leaves can also add a pop of color and freshness to each plate.
  3. Slice with Care: Use a sharp knife dipped in warm water to slice the cheesecake cleanly. Wipe the knife clean between cuts to ensure neat slices without sticking.
  4. Individual Portions: For a more elegant presentation, consider using a biscuit cutter to cut individual rounds of cheesecake. Serve each round on a dessert plate with a drizzle of caramel sauce or a sprinkle of powdered sugar for an upscale twist.


  1. Refrigeration is Key: Store any leftover pineapple upside-down cheesecake in the refrigerator in an airtight container or covered with plastic wrap or foil. The cheesecake will keep well for up to 3-4 days, though it’s best enjoyed within the first 2 days for optimal freshness.
  2. Avoid Freezing: While cheesecake can technically be frozen, the texture may suffer upon thawing, and the pineapple topping may become watery. If you must freeze leftovers, wrap individual slices tightly in plastic wrap and aluminum foil before placing them in an airtight container. Thaw overnight in the refrigerator before serving.
  3. Separate Storage: If storing leftover cheesecake slices, place a piece of parchment paper between each slice to prevent them from sticking together. This makes it easier to remove individual portions without damaging the cheesecake.

By following these serving and storage tips, you can ensure that your pineapple upside-down cheesecake remains fresh, flavorful, and ready to enjoy whenever the craving strikes.

Variations of the Recipe:

  1. Coconut Pineapple Cheesecake:
    • Add shredded coconut to the cheesecake filling for a tropical twist. You can also sprinkle toasted coconut on top of the pineapple topping for added texture and flavor.
  2. Rum-Infused Pineapple Upside-Down Cheesecake:
    • Soak the pineapple slices in rum before arranging them on the brown sugar mixture. You can also add a splash of rum to the cheesecake filling for a boozy kick.
  3. Mango Pineapple Cheesecake:
    • Replace some of the pineapple slices with slices of fresh mango for a sweet and tangy flavor combination. You can also blend mango into the cheesecake filling for a vibrant tropical twist.
  4. Pina Colada Cheesecake:
    • Incorporate flavors of the classic cocktail by adding coconut cream and pineapple juice to the cheesecake filling. Garnish each slice with a maraschino cherry and a sprinkle of toasted coconut for a fun and festive presentation.
  5. Mini Pineapple Upside-Down Cheesecakes:
    • Instead of making one large cheesecake, prepare individual mini cheesecakes in muffin tins or mini springform pans. Top each mini cheesecake with a pineapple slice, a cherry, and a drizzle of caramel sauce for adorable and bite-sized treats.

These variations offer creative ways to customize the classic pineapple upside-down cheesecake recipe and add new flavors and textures to this beloved dessert. Experiment with different ingredients and combinations to create your own signature cheesecake that will dazzle your taste buds.

Frequently Asked Questions (FAQs):

  1. Can I use canned pineapple instead of fresh for this recipe? Yes, canned pineapple slices can be used in place of fresh pineapple for convenience. Just be sure to drain them well before arranging them on the brown sugar mixture.
  2. How can I prevent the cheesecake from cracking? To prevent cracks, avoid overmixing the cheesecake batter and be sure to bake it in a water bath. Additionally, allowing the cheesecake to cool gradually in the oven with the door ajar can help prevent cracks from forming.
  3. Can I use a different fruit for the topping? Certainly! While pineapple is traditional, you can experiment with other fruits such as peaches, apricots, or even strawberries for a unique twist on the classic recipe.
  4. Can I make this cheesecake ahead of time? Yes, you can prepare the cheesecake up to 2 days in advance and store it in the refrigerator until ready to serve. Just be sure to cover it well to prevent it from absorbing any odors.
  5. How do I know when the cheesecake is done baking? The cheesecake is done when the edges are set, and the center is slightly jiggly. It will continue to set as it cools. Overbaking can lead to a dry and crumbly texture, so it’s best to err on the side of underbaking.
  6. Can I use a different type of crust for this cheesecake? Absolutely! While graham cracker crust is traditional, you can use crushed vanilla wafers, shortbread cookies, or even chocolate cookies for a different flavor profile.
  7. Is it necessary to refrigerate the cheesecake before serving? Yes, chilling the cheesecake in the refrigerator for at least 4 hours, or preferably overnight, allows it to firm up and develop its flavors. This step is essential for achieving the best texture and taste.
  8. Can I freeze leftover cheesecake? Yes, cheesecake freezes well. Wrap individual slices tightly in plastic wrap and aluminum foil before placing them in an airtight container. Thaw overnight in the refrigerator before serving.
  9. How long will the cheesecake last in the refrigerator? Properly stored, cheesecake will keep well in the refrigerator for up to 5-7 days. Be sure to cover it tightly to prevent it from drying out or absorbing any odors.
  10. Can I make this cheesecake without a springform pan? While a springform pan is ideal for cheesecakes, you can use a regular cake pan lined with parchment paper if needed. Just be sure to carefully invert the cheesecake onto a serving platter after baking to reveal the pineapple topping.

These FAQs provide helpful information for anyone looking to prepare pineapple upside-down cheesecake and troubleshoot any common issues that may arise.


Treat yourself to a slice of paradise with our luscious pineapple upside-down cheesecake. Whether enjoyed as a special dessert for a celebration or simply as a decadent indulgence on a sunny afternoon, this delightful dessert is sure to impress with its tropical flavors and creamy richness. Elevate your dessert game and transport your taste buds to the tropics with every blissful bite of this irresistible cheesecake.

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