If you love pineapple upside-down cake and rich, creamy cheesecake, this Pineapple Upside-Down Cheesecake is the ultimate dessert for you. Combining the caramelized fruit topping of a classic pineapple cake with the luscious texture of a cheesecake, this show-stopping treat is perfect for special occasions, summer gatherings, or simply indulging in something extraordinary. The buttery graham cracker crust, smooth cheesecake filling, and golden, syrupy pineapple slices create a harmony of flavors and textures that will leave everyone asking for seconds.
Why You’ll Love This Recipe
✔ Two Desserts in One – A fusion of classic cheesecake and pineapple upside-down cake.
✔ Creamy & Fruity Balance – The tangy pineapple contrasts beautifully with the velvety cheesecake.
✔ Make-Ahead Friendly – Perfect for preparing the day before an event.
✔ Stunning Presentation – Caramelized pineapple and cherries make this a visual masterpiece.
Ingredients
For the Crust:
- 1 ½ cups graham cracker crumbs – Adds a buttery, slightly crunchy base.
- 6 tablespoons unsalted butter, melted – Binds the crust together.
- 2 tablespoons granulated sugar – Enhances the sweetness and structure.
For the Cheesecake Filling:
- 2 (8-ounce) packages cream cheese, softened – The foundation for a rich, smooth texture.
- 1 ½ cups granulated sugar – Sweetens the filling.
- 1 teaspoon vanilla extract – Adds depth of flavor.
- 4 large eggs – Provide structure and help achieve a silky consistency.
- 1 (14-ounce) can sweetened condensed milk – Creates a creamy, luscious texture.
- 1 (20-ounce) can crushed pineapple, drained – Adds natural fruitiness and moisture.
For the Topping:
- 5 tablespoons melted butter – Creates the signature caramelized glaze.
- 2 tablespoons brown sugar – Enhances caramelization.
- 2 cans pineapple slices, drained – The key ingredient for the upside-down effect.
- 7 maraschino cherries, chopped – Adds a pop of color and sweetness.
Equipment Needed:
✔ 9-inch springform pan – Essential for easy removal of the cheesecake.
✔ Medium bowl – For mixing the crust ingredients.
✔ Electric mixer – Helps achieve a smooth and fluffy cheesecake filling.
✔ Large bowl – For mixing the cheesecake batter.
Step-by-Step Instructions
1. Prepare the Crust
- Preheat oven to 350°F (175°C).
- In a medium bowl, mix the graham cracker crumbs, melted butter, and sugar until well combined and crumbly.
- Press the mixture firmly into the bottom of the springform pan.
- Bake for 8-10 minutes, or until lightly golden. Let it cool completely before adding the filling.
2. Make the Cheesecake Filling
- In a large bowl, beat cream cheese with an electric mixer until smooth and creamy.
- Gradually add granulated sugar, beating until light and fluffy.
- Mix in vanilla extract for added flavor.
- Add the eggs one at a time, beating well after each addition.
- Stir in the sweetened condensed milk and drained crushed pineapple, ensuring everything is well combined.
3. Assemble & Bake the Cheesecake
- Pour the cheesecake filling into the cooled crust.
- Arrange the pineapple slices on top, slightly overlapping them.
- Sprinkle the chopped maraschino cherries evenly across the top.
- Bake at 350°F (175°C) for 1 hour and 15 minutes, or until the center is set but still slightly jiggly.
- Turn off the oven and let the cheesecake cool inside with the door slightly open for another hour to prevent cracking.
- Once fully cooled, refrigerate for at least 4 hours, preferably overnight, to allow flavors to meld and the cheesecake to firm up.
4. Invert & Serve
- Run a knife around the edge of the springform pan to loosen the cheesecake.
- Carefully remove the sides of the pan.
- Invert the cheesecake onto a serving plate—the caramelized pineapple and cherries should now be on top.
- Slice and serve chilled for the best texture and flavor.
Pro Tips for the Perfect Pineapple Upside-Down Cheesecake
✔ Use Full-Fat Cream Cheese – Ensures a richer, creamier texture.
✔ Drain Pineapple Well – Excess moisture can make the cheesecake too soft.
✔ Slow Cooling is Key – Prevents cracking and ensures a perfectly smooth top.
✔ For Extra Flavor – Add a teaspoon of rum extract or coconut extract to the cheesecake batter for a tropical twist.
✔ Use a Water Bath for Even Baking – Place the springform pan in a larger pan with hot water to prevent over-baking and cracks.
Serving Suggestions
- Drizzle with caramel sauce for extra indulgence.
- Serve with a dollop of whipped cream for a light contrast.
- Pair with a tropical fruit salad for a refreshing side.
- Enjoy with a cup of coffee or a piña colada for the ultimate treat.
Final Thoughts
This Pineapple Upside-Down Cheesecake is the perfect balance of sweet, creamy, and fruity flavors. The buttery graham cracker crust, smooth cheesecake filling, and caramelized pineapple topping create an unforgettable dessert that is as delicious as it is beautiful. Whether you’re serving it for a special occasion or simply treating yourself, this cheesecake will undoubtedly be the highlight of any meal.
Make it once, and it’s sure to become a family favorite!