If you love classic pineapple upside-down cake but crave something a little more indulgent and creamy, this Upside-Down Pineapple Cheesecake is the perfect dessert to satisfy that craving. Combining the caramelized sweetness of pineapple and brown sugar with the smooth richness of cheesecake, this recipe is a true crowd-pleaser. The graham cracker crust adds a subtle crunch, while maraschino cherries bring a pop of color and flavor that feels both nostalgic and elegant.
This cheesecake is ideal for special occasions like family gatherings, holiday dinners, or any time you want to impress guests with a homemade dessert that looks as stunning as it tastes. It requires a bit of patience but is surprisingly straightforward to make. Plus, prepping it ahead of time means you can relax and enjoy the event when it arrives.
Ingredients
5 tablespoons unsalted butter, melted (divided use)
2 tablespoons brown sugar (for caramelizing pineapple)
2 cans (8 ounces each) pineapple slices, drained thoroughly
7 maraschino cherries (whole or chopped for garnish)
1 cup graham cracker crumbs (about 8 full sheets, crushed finely)
3 tablespoons white sugar (for crust)
3 (8-ounce) tubs cream cheese, softened at room temperature (24 ounces total)
¾ cup heavy cream, cold
2 teaspoons vanilla extract
3 large eggs, at room temperature
Equipment
9-inch round non-stick skillet or springform pan
Electric mixer (stand or handheld)
Mixing bowls
Rubber spatula
Wire cooling rack
Oven thermometer (optional but recommended)
Step-by-Step Instructions
Step 1: Preheat the Oven
Set your oven to 325°F (165°C). Use an oven thermometer if available to ensure consistent baking temperature, which is crucial for a smooth cheesecake texture.
Step 2: Make the Caramelized Pineapple Base
In your 9-inch round skillet or cake pan, combine 2 tablespoons melted butter with 2 tablespoons brown sugar. Stir until smooth and thick.
Spread this mixture evenly across the bottom of the pan to create a rich caramel layer.
This mixture will bubble and caramelize during baking, so be sure it covers the base well but isn’t too thick.
Step 3: Arrange Pineapple and Cherries
Drain the pineapple slices thoroughly to avoid excess moisture.
Place the pineapple slices carefully on top of the caramel base in a single even layer.
Place one maraschino cherry in the center of each pineapple slice for classic presentation and a burst of color.
Step 4: Prepare the Graham Cracker Crust
In a small bowl, mix 1 cup graham cracker crumbs with 3 tablespoons melted butter and 3 tablespoons white sugar.
Stir until the crumbs are evenly moistened and crumbly.
Sprinkle or gently press this mixture evenly over the pineapple slices. This adds a crunchy texture that contrasts beautifully with the creamy cheesecake.
Step 5: Make the Cheesecake Filling
In a large mixing bowl, beat the softened cream cheese and ¾ cup white sugar together using an electric mixer on medium speed. Beat until smooth and creamy, about 2–3 minutes.
Add ¾ cup cold heavy cream and 2 teaspoons vanilla extract, then mix on low speed until fully combined and smooth.
Step 6: Add the Eggs
Add the eggs one at a time, mixing on low speed after each addition. Be careful not to overmix; just blend until combined to keep the cheesecake light and prevent cracking.
Step 7: Assemble and Bake
Pour the cream cheese mixture evenly over the prepared pineapple and graham cracker layers in your pan.
Place the pan on the middle rack of your preheated oven. Bake for about 55 to 60 minutes. The edges should be set, but the center will still jiggle slightly when gently shaken.
Avoid opening the oven door during the first 45 minutes to maintain a steady temperature.
Step 8: Cool and Loosen Edges
Remove the cheesecake from the oven and run a thin knife or spatula around the edges to loosen it from the pan. This helps prevent cracking as it cools.
Let the cheesecake cool completely on a wire rack for about 30 minutes.
Step 9: Chill and Serve
Once cooled, carefully invert the cheesecake onto a serving plate so the pineapple and cherries are on top, creating the iconic upside-down effect.
Refrigerate for at least 3 hours (preferably overnight) to allow it to fully set and the flavors to meld.
Serve chilled and enjoy the perfect balance of caramelized fruit, creamy cheesecake, and crunchy crust.
Tips for Success
Room temperature ingredients: Make sure cream cheese, eggs, and cream are at room temperature to avoid lumps and ensure smooth mixing.
Drain pineapple well: Excess juice can make the crust soggy and the cheesecake watery.
Use a water bath (optional): For even more delicate texture, place the cheesecake pan inside a larger pan filled with hot water while baking. Wrap the bottom of the pan in foil to prevent leaks.
Storage: Keep leftovers covered in the fridge for up to 4 days.
Enjoy this impressive yet approachable dessert that combines classic flavors with creamy richness—guaranteed to be a hit at your next celebration!
