Irresistible Pineapple Upside Down Cheesecake Recipe

Pineapple Upside Down Cheesecake Recipe – get ready to elevate your dessert game to an entirely new level! Have you ever dreamt of a dessert that perfectly marries the nostalgic charm of a classic pineapple upside-down cake with the luscious, creamy decadence of a velvety cheesecake? Well, prepare for that dream to become a delicious reality. I am absolutely thrilled to share this unique creation with you, a dish that captures the best of both beloved worlds.

The original pineapple upside-down cake found its fame in the early 20th century, thanks to the accessibility of canned pineapple, quickly becoming a staple in American homes for its striking presentation and delightful flavor. Cheesecake, on the other hand, boasts an ancient lineage, evolving from simple honey cakes into the rich, dairy-based treat we adore today. This particular recipe doesn’t just combine them; it creates something truly extraordinary. People adore this combination for its incredible balance of flavors and textures: the sweet, tangy, caramelized pineapple, buttery brown sugar, and a hint of cherry provide a vibrant counterpoint to the smooth, rich, and slightly tart cream cheese filling, all nestled on a crisp graham cracker crust. It’s a show-stopping dessert that promises a burst of sunshine in every forkful.

This Pineapple Upside Down Cheesecake Recipe is more than just a sweet treat; it’s an experience. It’s perfect for special occasions, holiday gatherings, or simply when you want to impress yourself and your loved ones with something truly spectacular. I promise you, the effort is incredibly rewarding, yielding a dessert that is both visually stunning and exquisitely delicious.

this Recipe

Ingredients:

• For the Pineapple Topping:

• 6 tablespoons (85g) unsalted butter, melted
• ½ cup (100g) packed light brown sugar
• 1 can (20 ounces) pineapple rings in juice, well drained (reserve 2 tablespoons of juice for the filling if desired, otherwise discard)
• ½ cup maraschino cherries, halved and patted dry with a paper towel

• For the Graham Cracker Crust:

• 1 ½ cups (about 180g) graham cracker crumbs (from about 10-12 full sheets)
• ¼ cup (50g) granulated sugar
• 6 tablespoons (85g) unsalted butter, melted

• For the Cheesecake Filling:

• 4 packages (8 ounces each, 904g total) full-fat cream cheese, softened to room temperature
• 1 ¾ cups (350g) granulated sugar
• 1 tablespoon pure vanilla extract
• ¼ cup (60ml) sour cream, full-fat, at room temperature
• 1 tablespoon all-purpose flour (optional, helps prevent cracking)
• 5 large eggs, at room temperature

Preparation – The Pineapple Layer

1. Prepare your springform pan: We’ll be starting with the decorative pineapple layer that will eventually become the top of your Pineapple Upside Down Cheesecake Recipe. Take a 9-inch springform pan and wrap the outside bottom and sides securely with at least two layers of heavy-duty aluminum foil. This is crucial for preventing any water from seeping into your crust during the water bath baking process later on. Make sure the foil extends all the way up the sides of the pan.
2. Melt the butter for the topping: In a small saucepan or microwave-safe bowl, melt the 6 tablespoons of unsalted butter until fully liquid. Once melted, carefully pour this butter directly into the bottom of your prepared springform pan. Gently tilt the pan to ensure the butter evenly coats the entire bottom surface. This buttery layer will be the base for our caramelization.
3. Add the brown sugar: Evenly sprinkle the ½ cup of packed light brown sugar over the melted butter in the pan. Use your fingers or a small spoon to distribute it as uniformly as possible. This combination of butter and brown sugar will create a beautiful, rich caramel sauce that will beautifully coat your pineapple once inverted.
4. Arrange the pineapple rings: Carefully place the well-drained pineapple rings directly on top of the butter and brown sugar mixture. Arrange them in a single, decorative layer. I usually start by placing one ring directly in the center and then surrounding it with the remaining rings, slightly overlapping if necessary to cover as much of the pan bottom as possible. The goal here is to create an aesthetically pleasing pattern, as this will be the show-stopping top of your finished Pineapple Upside Down Cheesecake Recipe.
5. Place the maraschino cherries: Now for a pop of color! Take your halved maraschino cherries and gently nestle them into the center of each pineapple ring, or strategically place them in the gaps between the rings. Make sure they are patted dry beforehand to prevent excess moisture from affecting the caramelization. This vibrant red against the golden pineapple is truly captivating. Set this prepared pan aside while you work on the crust.

Building the Crust

6. Prepare the graham cracker crumbs: In a medium-sized bowl, combine the 1 ½ cups of graham cracker crumbs with the ¼ cup of granulated sugar. If you don’t have pre-crushed crumbs, you can easily make them by pulsing graham cracker sheets in a food processor until fine, or by placing them in a Ziploc bag and crushing them with a rolling pin. Aim for fine crumbs, but a few slightly larger pieces are perfectly fine for texture.
7. Combine with melted butter: Melt the remaining 6 tablespoons of unsalted butter. Pour the melted butter over the graham cracker and sugar mixture. Stir everything together thoroughly with a fork or spatula until the crumbs are evenly moistened and resemble wet sand. It’s important that every crumb is coated, as this is what binds our crust together.
8. Form the crust: Carefully pour the graham cracker mixture directly over the pineapple and cherry layer in your springform pan. Gently press the mixture down evenly over the fruit to form the crust. Use the back of a spoon or the bottom of a flat-bottomed glass to firmly and evenly press the crumbs into a compact layer. Make sure the crust is level and extends to the edges of the pan. This crust will become the sturdy base for our creamy cheesecake, so a firm, even pressing is key.
9. Pre-bake the crust: Place the springform pan with the crust and pineapple layer into an oven preheated to 350°F (175°C). Bake for 10 minutes. This short pre-bake helps to set the crust, making it less likely to get soggy once the cheesecake filling is added. After 10 minutes, remove the pan from the oven and set it aside to cool slightly while you prepare the cheesecake filling. You’ll notice the crust will be lightly golden and fragrant.

Crafting the Cheesecake Filling

10. Cream the cream cheese: In the large bowl of a stand mixer fitted with the paddle attachment, or using a large bowl and a handheld electric mixer, beat the softened cream cheese on medium speed. Beat it for about 2-3 minutes, scraping down the sides of the bowl frequently, until it is completely smooth and free of any lumps. Having the cream cheese at proper room temperature is paramount for a lump-free, silky smooth cheesecake filling. Cold cream cheese will inevitably lead to lumps and an uneven texture.
11. Add sugar and vanilla: Gradually add the 1 ¾ cups of granulated sugar to the creamed cheese, beating on low to medium speed until just combined, about 2 minutes. Then, mix in the 1 tablespoon of pure vanilla extract. Continue to scrape down the sides of the bowl often to ensure all ingredients are thoroughly incorporated. We want to avoid overmixing at this stage, as incorporating too much air can lead to cracks in your finished Pineapple Upside Down Cheesecake Recipe.
12. Incorporate sour cream and flour: Add the ¼ cup of full-fat sour cream (also at room temperature) and the optional 1 tablespoon of all-purpose flour. The sour cream adds a wonderful tang and extra creaminess, while the flour acts as a stabilizer, providing a bit of structure to help prevent cracks during baking. Mix on low speed until just combined, once again scraping down the sides of the bowl.
13. Add eggs one at a time: This is a critical step for preventing cracks. Add the 5 large eggs, one at a time, to the cheesecake mixture. After each egg, beat on very low speed until just incorporated before adding the next. It is vital not to overmix the eggs. Overmixing at this stage incorporates too much air, which expands during baking and then collapses as the cheesecake cools, leading to unsightly cracks. Use the lowest speed possible and stop mixing as soon as the yolk disappears into the batter. The mixture should still look thick and rich. If desired, you can gently fold in 2 tablespoons of the reserved pineapple juice from the canned rings for an extra burst of pineapple flavor in the filling itself.

Assembling and Baking the Cheesecake

14. Prepare for the water bath: Place a large roasting pan (one that is larger than your springform pan) on the middle rack of your oven. Carefully place your foil-wrapped springform pan, containing the crust and pineapple layer, into the center of this roasting pan.
15. Pour the filling: Gently and slowly pour the prepared cheesecake filling over the pre-baked crust and pineapple layer in the springform pan. Use a rubber spatula to scrape out all the delicious filling from the mixing bowl, ensuring an even layer. Gently tap the pan a few times on the counter to release any large air bubbles that might be trapped.
16. Create the water bath: Carefully pour hot water into the larger roasting pan, surrounding the springform pan. Pour enough hot water so that it comes about halfway up the sides of the springform pan. Be extremely careful not to get any water into the cheesecake filling itself. A water bath creates a moist, even heat environment, which helps the cheesecake bake slowly and evenly, preventing the top from drying out and cracking.
17. Bake the cheesecake: Bake the cheesecake in the preheated oven at 350°F (175°C) for 15 minutes. After 15 minutes, reduce the oven temperature to 325°F (160°C) and continue baking for an additional 60-80 minutes, or until the edges are set and slightly puffed, but the center 2-3 inches still jiggles slightly when the pan is gently nudged. Do not overbake. The residual heat will continue to cook the center as it cools. Overbaking is a common cause of cracks in cheesecakes.

Cooling and Chilling for Perfection

18. Gradual cooling in the oven: Once the baking time is complete and the cheesecake has the right jiggle, turn off the oven. Leave the cheesecake in the water bath inside the oven with the oven door propped open a few inches (you can use a wooden spoon handle). Allow the cheesecake to cool in the gradually decreasing heat of the oven for 1 hour. This slow cooling process is absolutely essential for preventing drastic temperature changes that can lead to cracks.
19. Cooling at room temperature: After 1 hour in the oven, carefully remove the roasting pan from the oven. Using oven mitts, carefully lift the springform pan out of the water bath and remove the aluminum foil. Place the springform pan on a wire rack to cool completely to room temperature. This can take anywhere from 2 to 4 hours, depending on your kitchen’s temperature.
20. Chilling for setting: Once the cheesecake has reached room temperature, loosely cover it with plastic wrap and transfer it to the refrigerator. Chill for a minimum of 6-8 hours, but ideally overnight. Chilling is crucial for the cheesecake to fully set, firm up, and allow its flavors to meld and deepen. This step cannot be rushed for the perfect slice of Pineapple Upside Down Cheesecake Recipe.
21. Inverting the cheesecake: This is the moment of truth! After the cheesecake is thoroughly chilled, run a thin knife around the edge of the cheesecake, between the crust and the springform pan wall, to ensure it doesn’t stick. Release the clasp of the springform pan and carefully remove the ring.

    Now, place a flat serving plate (one without a lip, if possible) upside down on top of the cheesecake. Holding both the cheesecake and the plate firmly together, quickly and confidently flip the cheesecake over so that the plate is now on the bottom. Remove the bottom of the springform pan, which should now reveal your beautifully caramelized pineapple and cherry topping. If any fruit pieces stick to the pan bottom, carefully reattach them to the cheesecake. This upside-down reveal is the star of our Pineapple Upside Down Cheesecake Recipe.

Serving Your Pineapple Upside Down Cheesecake

22. Slicing and garnishing: For clean slices, dip a sharp knife in hot water and wipe it clean between each cut. This will ensure that your beautiful pineapple topping remains pristine. Serve individual slices of your gorgeous Pineapple Upside Down Cheesecake Recipe. It’s absolutely delightful on its own, but a dollop of freshly whipped cream or a small sprig of fresh mint can elevate its presentation and taste even further.
23. Storage: Store any leftover cheesecake covered loosely with plastic wrap or in an airtight container in the refrigerator for up to 4-5 days. While it’s best enjoyed fresh, the flavors can sometimes deepen beautifully after a day or two in the fridge.

<h2>Conclusion:</h2>
<p>As we reach the sweet finale of our culinary journey, I truly hope you’re feeling as excited as I am about trying this incredible dessert. This isn’t just another cheesecake recipe; it’s a celebration of flavors, a harmonious blend of the familiar and the delightfully unexpected. We’ve taken the comforting richness of a classic cheesecake, infused it with the tropical tang of caramelized pineapple, and presented it with an upside-down flourish that’s simply captivating. It’s the kind of dessert that stops conversations, sparks joy, and becomes the talking point of any gathering. The golden, syrupy pineapple slices nestled atop the creamy, velvety cheesecake, all sitting on a crunchy, buttery crust – it’s a textural and flavor masterpiece that you absolutely deserve to experience.</p>

<h4>Why This <strong>Pineapple Upside Down Cheesecake Recipe</strong> is a Game-Changer:</h4>
<p>What makes this particular <strong>Pineapple Upside Down Cheesecake Recipe</strong> truly outstanding? It’s the perfect synergy of sweetness and acidity. The brown sugar caramelization of the pineapple adds a deep, malty sweetness that beautifully cuts through the creamy tang of the cheesecake filling. And let’s not forget the visual appeal! That stunning mosaic of pineapple rings and maraschino cherries isn’t just for show; it promises the burst of tropical flavor that awaits. This cheesecake delivers on every front: it’s decadent, refreshing, visually spectacular, and surprisingly approachable for home bakers. It elevates your dessert game without demanding Michelin-star skills. I promise you, one bite of this luscious creation and you’ll understand why it’s become one of my absolute favorite showstoppers.</p>

<h4>Serving Suggestions & Creative Variations to Explore</h4>
<p>While this cheesecake is undeniably magnificent on its own, there are wonderful ways to enhance the experience or even put your own spin on it. For serving, I love it slightly chilled, allowing the flavors to fully meld. A dollop of freshly whipped cream, perhaps infused with a hint of coconut extract, would be absolutely divine. If you want to lean into the tropical vibe even further, a sprinkle of toasted shredded coconut flakes or a few fresh mint leaves for garnish adds both visual appeal and a burst of freshness. For those who enjoy a bit more indulgence, a small scoop of vanilla bean ice cream or a drizzle of warm caramel sauce could take it to another level of luxury.</p>
<p>Feeling adventurous? This recipe is incredibly versatile! You could experiment with different fruits in the “upside-down” layer. Imagine caramelized peaches or even thinly sliced mango for a different tropical twist. Just ensure your chosen fruit holds up well to baking and caramelization. For the crust, while a graham cracker crust is classic, consider a shortbread cookie crust for a richer, buttery base, or even a gingersnap crust if you enjoy a touch of spice. You could also infuse the cheesecake filling itself with a dash of rum extract or a hint of ground cardamom to complement the pineapple beautifully. For smaller gatherings or individual portions, bake this recipe in a muffin tin with liners to create delightful mini Pineapple Upside Down Cheesecakes – perfect for parties or portion control. Remember, baking is about expression, so don’t be afraid to make this recipe truly your own!</p>

<h4>Your Turn to Bake and Share!</h4>
<p>Now that you have all the tools, tips, and inspiration, it’s time to preheat that oven and embark on your own cheesecake adventure! I wholeheartedly encourage you to try this <strong>Pineapple Upside Down Cheesecake Recipe</strong> in your kitchen. Don’t be intimidated by the layers; each step is straightforward, and the reward is absolutely worth every minute of effort. The joy of baking something so beautiful and delicious, and then sharing it with loved ones, is truly incomparable. Imagine the smiles when you present this stunning dessert at your next family dinner, potluck, or celebratory event. It’s more than just a dessert; it’s a conversation starter, a mood enhancer, and a testament to the magic you can create with simple ingredients.</p>
<p>Once you’ve made your masterpiece, I would absolutely love to hear about your experience! Did you stick to the original recipe, or did you venture into some of the variations we discussed? What was your favorite part of the process, and, most importantly, how did it taste? Please feel free to share your photos and stories with me. Your feedback and creations inspire me and our entire community of fellow food enthusiasts. So, grab your springform pan, gather your ingredients, and get ready to bake a dessert that will undoubtedly earn you rave reviews. Happy baking, and I can’t wait to see your incredible Pineapple Upside Down Cheesecakes!</p>

Irresistible Pineapple Upside Down Cheesecake Recipe

Elevate your dessert game with this unique Pineapple Upside Down Cheesecake, perfectly marrying the nostalgic charm of a classic pineapple upside-down cake with the luscious, creamy decadence of a velvety cheesecake. This show-stopping dessert features sweet, tangy, caramelized pineapple, buttery brown sugar, and a hint of cherry, beautifully balanced by a smooth, rich, and slightly tart cream cheese filling, all nestled on a crisp graham cracker crust.

Prep Time
45 Minutes

Cook Time
35 Minutes

Total Time
16 Hours

Servings
12 servings

Ingredients

• 6 tablespoons (85g) unsalted butter, melted (for topping)
• ½ cup (100g) packed light brown sugar (for topping)
• 1 can (20 ounces) pineapple rings in juice, well drained (reserve 2 tablespoons juice optionally)
• ½ cup maraschino cherries, halved and patted dry
• 1 ½ cups (180g) graham cracker crumbs
• ¼ cup (50g) granulated sugar (for crust)
• 6 tablespoons (85g) unsalted butter, melted (for crust)
• 4 packages (8 ounces each, 904g total) full-fat cream cheese, softened to room temperature
• 1 ¾ cups (350g) granulated sugar (for filling)
• 1 tablespoon pure vanilla extract
• ¼ cup (60ml) full-fat sour cream, at room temperature
• 1 tablespoon all-purpose flour (optional, helps prevent cracking)
• 5 large eggs, at room temperature
• 2 tablespoons reserved pineapple juice (optional, for filling)

Instructions

1. Step 1
   Wrap a 9-inch springform pan securely with at least two layers of heavy-duty aluminum foil around the bottom and sides to prevent water seepage.
2. Step 2
   Pour 6 tablespoons of melted unsalted butter into the bottom of the prepared pan, tilting to evenly coat. Evenly sprinkle ½ cup of packed light brown sugar over the melted butter.
3. Step 3
   Carefully place the well-drained pineapple rings in a single, decorative layer over the butter and brown sugar. Nestlé halved, patted dry maraschino cherries into the center of each ring or in gaps. Set aside.
4. Step 4
   In a medium bowl, combine 1 ½ cups graham cracker crumbs with ¼ cup granulated sugar. Pour 6 tablespoons of melted unsalted butter over the mixture and stir until crumbs are evenly moistened.
5. Step 5
   Carefully pour the crumb mixture over the pineapple layer in the springform pan. Press firmly and evenly with a spoon or flat-bottomed glass to form a compact crust. Pre-bake in an oven preheated to 350°F (175°C) for 10 minutes. Remove and cool slightly.
6. Step 6
   In a large bowl, beat softened full-fat cream cheese on medium speed for 2-3 minutes, scraping down the sides, until completely smooth and lump-free.
7. Step 7
   Gradually add 1 ¾ cups granulated sugar, then 1 tablespoon pure vanilla extract. Beat on low to medium speed until just combined, scraping sides frequently. Avoid overmixing.
8. Step 8
   Add ¼ cup full-fat sour cream (room temperature) and 1 tablespoon optional all-purpose flour. Mix on low speed until just combined, scraping down the sides.
9. Step 9
   Add 5 large eggs, one at a time, beating on very low speed until just incorporated after each. Do not overmix. If desired, gently fold in 2 tablespoons of reserved pineapple juice for extra flavor.
10. Step 10
    Place the foil-wrapped springform pan into a larger roasting pan on the middle rack of your oven. Gently pour the prepared cheesecake filling over the pre-baked crust and pineapple layer. Tap the pan a few times to release air bubbles.
11. Step 11
    Carefully pour hot water into the larger roasting pan, surrounding the springform pan, until it comes about halfway up the sides. Bake at 350°F (175°C) for 15 minutes. Reduce oven temperature to 325°F (160°C) and continue baking for 60-80 minutes, until edges are set and center 2-3 inches still jiggles slightly. Do not overbake.
12. Step 12
    Once baking is complete, turn off the oven. Leave the cheesecake in the water bath inside the oven with the door propped open a few inches for 1 hour. This slow cooling prevents cracking.
13. Step 13
    Carefully remove the roasting pan from the oven. Lift the springform pan out of the water bath and remove the aluminum foil. Place the springform pan on a wire rack to cool completely to room temperature (2-4 hours).
14. Step 14
    Once cooled to room temperature, loosely cover with plastic wrap and transfer to the refrigerator. Chill for a minimum of 6-8 hours, ideally overnight, for the cheesecake to fully set and flavors to meld.
15. Step 15
    After chilling, run a thin knife around the edge of the cheesecake, release the springform clasp, and remove the ring. Place a flat serving plate upside down on top of the cheesecake, hold firmly, and quickly flip the cheesecake onto the plate. Carefully remove the bottom of the springform pan to reveal the caramelized pineapple topping. Slice with a sharp knife (dipped in hot water and wiped clean between cuts). For best flavor, let it sit at room temperature for 20-30 minutes before serving. Garnish with whipped cream or mint if desired.
16. Step 16
    Store leftover cheesecake covered loosely in the refrigerator for up to 4-5 days. Individual slices can be wrapped and frozen for up to a month; thaw overnight in the refrigerator.

Important Information

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.