Name: Decadent Pineapple Upside Down Cheesecake Recipe
Prep time: 1 h
Cook time: 1 h 25 min
Total time: 15 h
Yield: 12 servings
Ingredients: For the Pineapple Topping:; 1/2 cup (113g) unsalted butter, melted; 1 cup (200g) packed light brown sugar; 1 (20-ounce) can pineapple rings in juice, drained very well; 1/2 cup maraschino cherries, drained and patted dry; For the Crust:; 1 1/2 cups (about 180g) graham cracker crumbs; 1/4 cup (50g) granulated sugar; 6 tablespoons (85g) unsalted butter, melted; For the Cheesecake Filling:; 3 (8-ounce) packages full-fat cream cheese, softened to room temperature; 1 1/4 cups (250g) granulated sugar; 1/4 cup (60g) sour cream, at room temperature; 1 tablespoon pure vanilla extract; 4 large eggs, at room temperature

Pineapple Upside Down Cheesecake Recipe. Have you ever dreamed of a dessert that perfectly marries two beloved classics into one show-stopping creation? Imagine the sun-kissed, caramelized sweetness of a traditional pineapple upside-down cake fused seamlessly with the rich, velvety decadence of a creamy cheesecake. This culinary masterpiece isn’t just a dessert; it’s an experience, a delightful journey for your taste buds that promises to be the highlight of any gathering.

This extraordinary Pineapple Upside Down Cheesecake Recipe is designed to bring that magical combination right into your home.

While the iconic pineapple upside-down cake conjures images of charming mid-century American kitchens, celebrated for its unique presentation and delicious fruit-forward appeal, the humble cheesecake boasts an even more ancient and esteemed lineage, with its origins tracing back to ancient Greece. What makes this particular fusion so incredibly popular? It’s the irresistible contrast: the tangy, juicy pineapple topping providing a vibrant counterpoint to the smooth, luxurious cheesecake filling, all resting upon a perfectly buttery crust. People adore this dish not only for its stunning visual appeal but also for its complex layers of flavor and texture that truly tantalize the palate. Get ready to bake something truly unforgettable that will have everyone asking for the recipe!

Ingredients:

For the Pineapple Topping:
- 1/2 cup (113g) unsalted butter, melted. I always opt for unsalted so I can control the salt level myself.
- 1 cup (200g) packed light brown sugar. This is going to create that luscious, sticky caramel sauce.
- 1 (20-ounce) can pineapple rings in juice, drained very well. Make sure to pat them dry with paper towels to prevent too much moisture from affecting your topping.
- 1/2 cup maraschino cherries, drained and patted dry. These add a beautiful pop of color and a touch of classic flavor to our Pineapple Upside Down Cheesecake Recipe.
For the Crust:
- 1 1/2 cups (about 180g) graham cracker crumbs. You can use pre-made crumbs or crush about 10-12 full graham cracker sheets yourself.
- 1/4 cup (50g) granulated sugar. Just a touch of sweetness to complement the buttery crust.
- 6 tablespoons (85g) unsalted butter, melted. This binds the crumbs together beautifully.
For the Cheesecake Filling:
- 3 (8-ounce) packages full-fat cream cheese, softened to room temperature. This is absolutely crucial for a smooth, lump-free cheesecake. Trust me, cold cream cheese will leave you with a lumpy mess!
- 1 1/4 cups (250g) granulated sugar. For that perfect balance of sweetness against the tangy cream cheese.
- 1/4 cup (60g) sour cream, at room temperature. Sour cream adds a wonderful tang and helps create an incredibly creamy texture.
- 1 tablespoon pure vanilla extract. Don’t skimp on good vanilla; it makes all the difference!
- 4 large eggs, at room temperature. Just like the cream cheese, room temperature eggs incorporate more evenly into the batter.

Prepping Your Pan and Topping: The Foundation of Flavor

Prepare Your Springform Pan: Before we even think about mixing, let’s get our pan ready. Take a 9-inch springform pan. I always like to ensure no leaks, so I wrap the bottom and sides of the pan securely with a double layer of heavy-duty aluminum foil. This is not just for preventing leaks during the water bath (which we’ll get to!), but also to help hold in that delicious pineapple topping. Lightly grease the inside bottom and about 1 inch up the sides of the pan with a bit of butter or non-stick spray.
Create the Caramelized Pineapple Base: In a small, microwave-safe bowl or a saucepan over low heat, melt your 1/2 cup of unsalted butter. Once melted, pour this evenly into the bottom of your prepared springform pan.
Add the Brown Sugar: Sprinkle the 1 cup of packed light brown sugar evenly over the melted butter in the pan. Use your fingers or a spoon to gently spread it out as much as possible. This combination of butter and brown sugar will melt down during baking to form the most incredible, sticky-sweet caramel sauce that gives our Pineapple Upside Down Cheesecake Recipe its signature “upside down” characteristic.
Arrange the Pineapple Rings: Now for the fun part! Take your well-drained and patted-dry pineapple rings. Arrange them carefully and snugly over the brown sugar mixture. I like to start by placing one ring directly in the center. Then, I arrange the remaining rings around it, overlapping them slightly if necessary, to create a beautiful, continuous layer. The goal is to cover the entire bottom of the pan as much as possible. This is what you’ll see when you flip the cheesecake, so make it pretty!
Place the Maraschino Cherries: For that classic look, strategically place your drained maraschino cherries in the center of each pineapple ring, or artfully scatter them in the gaps between the rings. They add a vibrant splash of color and a lovely cherry sweetness. Set this pan aside gently while you prepare the crust and filling.

Crafting the Perfect Crust: A Buttery Base

Preheat Your Oven: Get your oven preheating to 350°F (175°C). We’ll be pre-baking the crust briefly, and then adjusting the temperature for the cheesecake itself.
Prepare the Graham Cracker Crumbs: In a medium-sized bowl, combine your 1 1/2 cups of graham cracker crumbs with the 1/4 cup of granulated sugar. Give it a good stir to ensure the sugar is evenly distributed. If you’re crushing your own crackers, aim for fine crumbs – you don’t want big chunks!
Add the Melted Butter: Pour the 6 tablespoons of melted unsalted butter over the crumb mixture. Using a fork or your clean fingertips, mix everything together until the crumbs are uniformly moistened. It should resemble wet sand and hold together when you press a small amount between your fingers. This butter is what binds the crust together.
Press the Crust: Carefully spoon the crumb mixture over the pineapple and cherry layer in your prepared springform pan. Gently, but firmly, press the crumbs into an even layer over the entire pineapple topping. I find using the bottom of a flat glass or a measuring cup works wonders for achieving a perfectly even and compact crust. Ensure it’s pressed firmly so it doesn’t crumble when you cut into your finished Pineapple Upside Down Cheesecake.
Pre-bake the Crust: Place the springform pan (with the pineapple topping and crust) into your preheated oven. Bake for just 8-10 minutes. This quick pre-bake helps to set the crust, preventing it from becoming soggy once the cheesecake filling is added. After 8-10 minutes, remove the pan from the oven and set it aside to cool slightly while you prepare the filling. Do not turn off your oven yet! We will lower the temperature soon.

Whipping Up the Dreamy Cheesecake Filling: Creamy Perfection

Prepare for the Filling: Make sure all your cheesecake filling ingredients are at room temperature. This is crucial for a smooth, lump-free batter. Cold cream cheese leads to lumps, and cold eggs don’t emulsify as well.
Cream the Cream Cheese: In the bowl of a stand mixer fitted with the paddle attachment, or using a large bowl and a handheld electric mixer, beat the 3 packages of softened full-fat cream cheese on medium speed for about 2-3 minutes. You want it to be incredibly smooth, light, and completely free of any lumps. Scrape down the sides and bottom of the bowl frequently to ensure everything is incorporated.
Add Sugar and Sour Cream: Gradually add the 1 1/4 cups of granulated sugar to the creamed cream cheese, beating on low to medium speed until just combined and smooth, about 1-2 minutes. Avoid over-beating here. Then, mix in the 1/4 cup of room temperature sour cream and the 1 tablespoon of pure vanilla extract until just incorporated. Scrape down the bowl one last time.
Incorporate the Eggs: This step is very important for preventing cracks in your cheesecake. Add the 4 large room temperature eggs, one at a time, beating on low speed only until each egg is just combined with the mixture. As soon as the yolk disappears, stop mixing and add the next egg. Over-mixing the eggs can incorporate too much air into the batter, which can cause the cheesecake to puff up too much during baking and then crack as it cools. We want a dense, creamy texture for our Pineapple Upside Down Cheesecake.

Assembling and Baking: The Patience Game

Lower Oven Temperature: Reduce your oven temperature to 325°F (160°C). This lower temperature is ideal for baking cheesecakes gently and evenly.
Prepare the Water Bath (Bain-Marie): This is arguably the most important step for a crack-free, perfectly creamy cheesecake. Place your foil-wrapped springform pan (with the pineapple, crust, and soon-to-be filling) inside a larger roasting pan.
Pour the Filling: Carefully and slowly pour the prepared cheesecake filling over the pre-baked crust and pineapple topping in the springform pan. Gently tap the pan on your counter a few times to release any large air bubbles.
Fill the Water Bath: Transfer the roasting pan with the springform pan to the oven. Once it’s on the oven rack, carefully pour hot water into the larger roasting pan, making sure the water comes halfway up the sides of the springform pan. Be extremely careful not to get any water into the cheesecake itself! The water bath provides a moist, even heat that prevents cracking and ensures a silky-smooth texture.
Bake the Cheesecake: Bake for 60-75 minutes, or until the edges are set but the center still has a slight jiggle (about 2-3 inches in the center) when you gently shake the pan. The residual heat will continue to cook the center as it cools. Avoid overbaking, as this is a common cause of cracks.

Cooling, Chilling, and The Grand Reveal: Flipping Our Pineapple Upside Down Cheesecake

Gradual Cooling in the Oven: Once the baking time is complete, turn off the oven but leave the cheesecake inside with the oven door propped open slightly (I use a wooden spoon). Let it cool in the gradually decreasing heat of the oven for 1 hour. This slow cooling process is another key factor in preventing cracks.
Cooling at Room Temperature: After 1 hour in the oven, carefully remove the entire roasting pan from the oven. Carefully lift the springform pan out of the water bath and remove the foil. Place the cheesecake on a wire rack and allow it to cool completely to room temperature, which will take another 2-3 hours. Patience is truly a virtue with cheesecakes!
The Essential Chill: Once it’s at room temperature, cover the springform pan loosely with plastic wrap and transfer it to the refrigerator. Chill the cheesecake for at least 6-8 hours, but ideally overnight. This extended chilling time is absolutely critical for the cheesecake to firm up properly, for the flavors to meld beautifully, and to ensure it holds its shape when sliced. It’s also crucial for the “upside down” effect to set properly.
The Grand Inversion – Time to Flip!: This is the most exciting part of making this Pineapple Upside Down Cheesecake Recipe! Once thoroughly chilled, remove the cheesecake from the refrigerator. Run a thin knife or offset spatula carefully around the edge of the cheesecake to loosen it from the sides of the pan. Unclasp and remove the springform ring.
Flipping Technique: Now for the flip! Place a large serving plate or platter upside down over the top of the cheesecake. Holding both the plate and the bottom of the springform pan firmly together, quickly and confidently flip the cheesecake over onto the serving plate. Gently lift off the bottom of the springform pan. If any pineapple or caramel sticks, don’t panic! You can carefully scrape it off the pan bottom with a spatula and reattach it to the cheesecake. Admire your beautiful, caramelized Pineapple Upside Down Cheesecake!
Serving: Slice your beautiful creation with a sharp knife, wiping the blade clean between each slice for the cleanest cuts. Serve chilled and enjoy the stunning presentation and incredible flavor of this unique dessert!

Conclusion:

Well, my friends, we’ve reached the sweet end of our journey with what I truly believe is one of the most exciting dessert innovations you’ll ever encounter. This isn’t just another cheesecake; it’s a culinary masterpiece that seamlessly marries the creamy, tangy indulgence of a classic cheesecake with the sticky, caramelized fruitiness of a beloved pineapple upside-down cake. I’m talking about the truly magnificent Pineapple Upside Down Cheesecake Recipe we’ve just explored. What makes this a non-negotiable addition to your baking repertoire is its sheer ability to surprise and delight. Imagine cutting into a perfectly golden-brown crust, through a thick layer of velvety smooth, rich cream cheese filling, only to discover a vibrant, glistening topping of caramelized pineapple rings and Maraschino cherries. The textural contrast is divine – the tender, juicy pineapple cutting through the dense, cool cheesecake, all anchored by a subtly sweet, buttery crust. It’s a dessert that demands attention, a showstopper that will undoubtedly spark conversations and earn you rave reviews. It’s not just a dessert; it’s an experience, a harmonious blend of two iconic treats that, when combined, create something even greater than the sum of their parts. Every bite is a journey through sweet, tart, creamy, and wonderfully fruity notes, making it an absolute triumph of flavor and presentation.

Now that you’ve mastered the art of creating this sensational dessert, let’s talk about how to make it an even more memorable occasion, or how to put your own unique spin on it.

Serving Temperature:

For optimal enjoyment, I personally find that this cheesecake truly shines when it’s served chilled, straight from the refrigerator. The cool temperature enhances the creaminess of the filling and provides a refreshing contrast to the sweet pineapple. However, if you prefer a slightly softer, more “melt-in-your-mouth” texture, letting it sit at room temperature for about 15-20 minutes before serving can also be delightful. This allows the flavors to open up just a touch more, offering a subtly different but equally enjoyable experience. Experiment a little to discover your personal preference!

Perfect Pairings:

Consider pairing a slice with a strong, dark roast coffee to cut through the richness, or a delicate cup of herbal tea for a more relaxed experience. For an extra touch of decadence, a scoop of vanilla bean ice cream or a generous dollop of freshly whipped cream alongside each slice would be absolutely heavenly. The cool, plain ice cream or airy whipped cream provides a wonderful textural and temperature contrast that elevates the entire dish. If you’re feeling celebratory, a glass of sparkling wine or a light Moscato would complement the pineapple beautifully, their effervescence and fruity notes dancing harmoniously with the cheesecake.

Garnishing for Grandeur:

While the pineapple topping is already stunning, a little extra garnish never hurts! A few fresh mint leaves can add a pop of vibrant green color and a fresh, aromatic counterpoint that cleanses the palate. A sprinkle of toasted coconut flakes could introduce another layer of tropical flavor and a lovely, subtle crunch, truly leaning into the island vibes of the pineapple. Or, for a truly classic look that harks back to its pineapple upside-down cake origins, place an extra Maraschino cherry or two strategically on top of the pineapple rings. A light dusting of powdered sugar just before serving can also add a touch of elegance.

Creative Variations to Explore:

Don’t be afraid to experiment once you’ve nailed the original recipe! This is where your culinary creativity can truly shine.

Different Fruits: While pineapple is classic, imagine a peach upside-down cheesecake, using beautifully ripe, caramelized peach slices. Or, for a different twist, try a mixed berry version with raspberries and blueberries nestled into a caramelized sugar base, offering a burst of tartness. Even sliced apples or pears could work beautifully for a more autumnal feel.
Citrus Zest: Adding lemon or lime zest directly to the cheesecake batter could provide a wonderful bright, zesty counterpoint to the sweetness of the pineapple and the richness of the cream cheese, lifting the entire flavor profile.
Crust Alternatives: A ginger snap crust could add a spicy warmth that pairs surprisingly well with pineapple, offering an unexpected complexity. Alternatively, a coconut cookie crust would lean even further into the tropical vibe, enhancing the overall flavor profile. For a lighter touch, you could even try a shortbread crust.
Individual Servings: For parties or a more elegant presentation, consider making mini cheesecakes in muffin tins or small ramekins. This makes for elegant, pre-portioned desserts that are easy to serve and customize. Just remember to adjust baking times accordingly, as smaller cheesecakes will bake much faster.

The possibilities are truly endless once you understand the core mechanics of this brilliant recipe.

I genuinely hope you feel inspired and ready to tackle this incredible Pineapple Upside Down Cheesecake Recipe in your own kitchen. There’s an immense sense of satisfaction that comes from creating something so beautiful and delicious from scratch. Don’t be intimidated; the steps are straightforward, and the reward is absolutely worth every moment of effort. I urge you to set aside some time, gather your ingredients, and embark on this delightful baking adventure. Once you’ve pulled your masterpiece from the oven, let it chill completely, slice into it, and savor every single bite. Let the blend of creamy, tangy, and sweet flavors wash over you. But don’t keep this joy all to yourself! I’d absolutely love to hear about your experience. Did you try a variation? What was your favorite part? Did it become an instant hit with your family and friends? Please share your triumphs, your tips, and especially your photos! Your feedback not only brightens my day but also helps inspire other bakers in our community to try this fantastic dessert. Let’s celebrate the art of baking together. Happy baking, and I can’t wait to see your stunning creations!