Pineapple Right Side Up Cheesecake is pure dessert magic: luscious, velvety cheesecake layered over tangy caramelized pineapple rings and a buttery graham cracker crust, finished with sweet maraschino cherries for that nostalgic, show-stopping effect. Every bite delivers a tropical burst that’s as stunning to look at as it is divine to eat. If you’re looking for a twist on pineapple upside-down cake and can’t resist the creaminess of a classic cheesecake, this treat brings you the best of both worlds—it’s a dessert that practically demands celebration!

Pineapple Right Side Up Cheesecake Recipe - Recipe Image

Ingredients You’ll Need

What makes Pineapple Right Side Up Cheesecake so irresistible? It’s the stellar cast of everyday ingredients, working together in perfect harmony. Each one serves its own role in building that dreamy tropical flavor and unforgettable texture. Here’s what you’ll need, along with insider tips to help you create your cheesecake masterpiece:

Graham Cracker Crumbs: These are the foundation of your crust, offering a sweet, crumbly base that perfectly balances the creamy cheesecake layer.
Granulated Sugar: Split between the crust and the filling, it keeps things just sweet enough without being cloying.
Unsalted Butter: Melted into the crust for richness, and also used in the decadent pineapple topping for extra flavor.
Brown Sugar: Adds caramel notes to the pineapple topping and makes those rings gloriously sticky and golden.
Pineapple Rings (Canned or Fresh): The bright, tangy star of the show—use fresh for more zing or canned for pure simplicity.
Maraschino Cherries: Pop one in each pineapple ring; they add nostalgia and a pop of color that’s totally charming.
Cream Cheese: The heart of the cheesecake layer—be sure it’s softened for the creamiest, smoothest texture.
Large Eggs: They bind everything together and give your cheesecake its classic, rich structure.
Sour Cream: Adds tang and keeps the filling unbelievably silky and light.
Vanilla Extract: A teaspoon boosts the cheesecake’s warmth and rounds out the tropical fruit flavors.
Crushed Pineapple (Well Drained): Mixed right into the batter, this infuses every bite with juicy sweetness—just drain well to avoid a watery cheesecake.

How to Make Pineapple Right Side Up Cheesecake

Step 1: Prep Your Pan and Oven

Start by preheating your oven to 325°F. Line the bottom of a 9-inch springform pan with parchment paper for effortless removal, and tightly wrap the outside with foil—this keeps water from the bath from sneaking in. This little bit of prep ensures both a smooth release and a beautifully even bake.

Step 2: Make the Graham Cracker Crust

Combine your graham cracker crumbs, granulated sugar, and melted butter in a bowl. Mix until every crumb looks like wet sand, then press the mixture firmly and evenly into the bottom of your pan. The crust sets the stage for flavor and texture, so make sure it’s packed down tightly—you want just the right amount of crunch beneath all that creamy filling.

Step 3: Prepare the Pineapple Topping

Melt the brown sugar and butter in a small saucepan until bubbling and thick. Pour this sweet layer over the crust, then carefully arrange your pineapple rings over the gooey base. Nestle a maraschino cherry in the center of each pineapple ring. This upside-down magic sets up the stunning pattern that makes Pineapple Right Side Up Cheesecake so eye-catching.

Step 4: Mix the Cheesecake Filling

In a large mixing bowl, beat the softened cream cheese and granulated sugar until velvety smooth—no lumps allowed! Add your eggs one at a time, mixing on low speed until just combined (this keeps air bubbles at bay). Gently fold in the sour cream, vanilla, and well-drained crushed pineapple to keep the filling light and lush. Be careful not to overmix!

Step 5: Assemble and Bake

Pour your creamy cheesecake batter over the pineapple-cherry layer, gently smoothing the top. Place the springform pan inside a larger roasting pan and pour hot water halfway up the sides to create a moist environment. Bake for 55–65 minutes, or until the center is set but still just a bit jiggly—think of it as a gentle wobbly dance.

Step 6: Cool and Chill

Once baked, turn off the oven, crack the door, and let your cheesecake rest for another hour—this helps prevent cracks. Then, move it to the fridge and let it chill for at least 4 hours (overnight is best!). This wait is tough, but it’s so worth it for a perfectly set, easy-to-slice dessert.

Step 7: Invert and Serve

When you’re ready to serve, remove the pan sides and carefully invert your cheesecake onto a serving plate, so the pineapple topping is showcased in all its golden glory. It’s the breathtaking grand finale!

How to Serve Pineapple Right Side Up Cheesecake

Garnishes

To highlight the tropical beauty, scatter a few extra maraschino cherries or pineapple tidbits around the base, and give it a light dusting of powdered sugar for a touch of elegance. Even a sprig of mint can elevate the color palette and freshness. The key is to let those caramelized pineapple rings and cherries remain the star.

Side Dishes

Pair this cheesecake with refreshing options like a simple fruit salad or a scoop of coconut sorbet. A hot cup of coffee or lightly brewed tea complements the bright, sweet flavors perfectly, creating a well-balanced dessert course that’s just right for brunch or a festive evening treat.

Creative Ways to Present

You can slice and serve Pineapple Right Side Up Cheesecake as individual wedges on colorful plates, or go upscale with small cubes as part of a dessert buffet. For a playful twist, layer chopped servings into mini jars for picnic-friendly parfaits, or crumble the crust to make cheesecake trifle cups. However you present it, this dessert always stuns!

Make Ahead and Storage

Storing Leftovers

If you find yourself with extra slices (a rare event!), cover the cheesecake tightly with plastic wrap or place it in an airtight container. It will stay fresh in the fridge for up to five days, maintaining its creamy texture and lively flavor—although it’s usually snapped up much sooner.

Freezing

Pineapple Right Side Up Cheesecake freezes wonderfully. Chill the cheesecake thoroughly first, then wrap slices or the whole cake tightly in plastic wrap and a layer of aluminum foil. It can be frozen for up to a month. When you’re ready to enjoy it, thaw overnight in the refrigerator for best results.

Reheating

This cheesecake is best served chilled or at cool room temperature; there’s no need to reheat. If you prefer a softer bite, let slices sit at room temp for about 10–15 minutes before serving. Warm cheesecake is not recommended, as it can lose its luscious structure and the topping may slide off.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple brings a vibrant, slightly tangier flavor and a firmer texture. Just make sure to cut the rings thin and pat them dry thoroughly, as extra juice can make the topping runny and affect how the cake sets.

How do I prevent my cheesecake from cracking?

The water bath and gradual cooling are your best friends here. Don’t skip wrapping your pan with foil and always let your cheesecake rest in the oven with the door cracked after baking—this helps the filling set gently and minimizes cracks.

Can I make Pineapple Right Side Up Cheesecake in advance?

Yes! This cheesecake is ideal for making a day ahead. Simply prepare, bake, cool, and chill overnight. This rest time helps flavors develop and ensures neat, beautiful slices when you invert and serve.

What’s the best way to invert the cheesecake?

After chilling thoroughly, run a thin knife around the inside edge to loosen, then place a flat serving plate over the cheesecake and carefully invert in one quick motion. Remove the pan base and parchment to reveal your caramelized pineapple topping!

Can I skip the water bath?

While you technically can, the water bath is what guarantees that silky, crack-free texture and even bake. If you’re short on time, you can bake without it, but your cheesecake may have a different texture and is more likely to crack.

Final Thoughts

If you’re craving something that’s equal parts stunning and scrumptious, you have to give Pineapple Right Side Up Cheesecake a try. It’s the ultimate tropical treat, blending the nostalgia of classic cakes with creamy, dreamy cheesecake. Your friends and family will be wowed, and you’ll be handing out the recipe in no time!

Pineapple Right Side Up Cheesecake Recipe

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4.6 from 20 reviews

Author: admin
Total Time: 1 hour 25 minutes (plus chilling)
Yield: 12 servings 1x
Diet: Non-Vegetarian

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Description

Indulge in the tropical flavors of this Pineapple Right Side Up Cheesecake that combines the classic pineapple upside-down cake with a creamy cheesecake twist. A show-stopping dessert perfect for any occasion!

Ingredients

Scale

For the crust:

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

For the topping:

1/2 cup packed brown sugar
1/4 cup unsalted butter
7 pineapple rings (canned or fresh)
7 maraschino cherries

For the filling:

3 packages (8 oz each) cream cheese, softened
1 cup granulated sugar
3 large eggs
1/2 cup sour cream
1 teaspoon vanilla extract
1/2 cup crushed pineapple, well drained

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Instructions

Prepare the crust: Preheat oven to 325°F. Mix graham cracker crumbs, sugar, and melted butter. Press into a 9-inch springform pan.
Make the topping: Melt brown sugar and butter in a saucepan. Pour into crust, arrange pineapple rings, and place cherries on top.
Prepare the filling: Beat cream cheese and sugar. Add eggs, sour cream, vanilla, and crushed pineapple. Pour over the topping.
Bake: Place the pan in a water bath, bake for 55–65 minutes. Let sit in the oven, then chill before serving.

Notes

Ensure crushed pineapple is well drained to avoid excess moisture.
This dessert beautifully marries the flavors of pineapple upside-down cake and creamy cheesecake.

Prep Time: 25 minutes
Cook Time: 1 hour
Category: Dessert
Method: Baking
Cuisine: American