This show-stopping dessert is the ultimate two-in-one treat! Buttery pineapple upside-down cake meets rich, creamy cheesecake—layered together for a dessert that’s as beautiful as it is delicious. Perfect for summer gatherings, birthdays, or anytime you want to impress.
Why You’ll Love It
🌟 Two desserts in one! Fluffy vanilla cake and creamy cheesecake in one epic slice.
🍒 Topped with fruit and caramelized brown sugar. Yes, please.
🎂 Make-ahead friendly. Prep the cheesecake the day before and assemble day-of.
💛 Perfect centerpiece dessert. Everyone will ask for seconds (and the recipe)!
Ingredients
Graham Cracker Crust
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1½ cups graham cracker crumbs
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1 teaspoon sugar
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6 tablespoons melted butter (salted or unsalted)
Cheesecake Layer
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(3) 8 oz packages cream cheese (Philadelphia preferred)
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1⅔ cups sugar
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¼ cup cornstarch
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1 tablespoon vanilla extract
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2 extra-large eggs
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¾ cup heavy cream
Pineapple Upside-Down Cake
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20 oz can pineapple slices in juice, drained
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½ cup brown sugar
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4 tablespoons salted butter
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Maraschino cherries (7 or more for your design)
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5 tablespoons salted butter, melted
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⅔ cup sugar
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2 large eggs
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½ cup buttermilk
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1 teaspoon baking powder
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1 teaspoon vanilla
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¼ teaspoon salt
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¼ teaspoon baking soda
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1¼ cups all-purpose flour
Step-by-Step Instructions
1. Make the Cheesecake (Day Before)
Prep the pan:
Preheat oven to 350°F. Wrap the outside of a 9-inch springform pan tightly in heavy-duty foil to prevent leaks.
Make the crust:
In a bowl, mix graham cracker crumbs, sugar, and melted butter. Press into the bottom (and slightly up the sides) of the pan. Bake for 8 minutes. Let cool.
Make the filling:
In a large bowl with a mixer on low speed, blend 1 package cream cheese, ⅓ cup sugar, and cornstarch until smooth (about 3 minutes). Add remaining cream cheese one block at a time, beating well. Stir in the rest of the sugar and vanilla. Add eggs one at a time, mixing well. Add heavy cream last—do not overmix.
Bake the cheesecake:
Place the pan in a larger roasting pan. Pour hot water into the outer pan until it reaches halfway up the sides of the springform. Bake for 1 hour 15 minutes, until set and lightly golden.
Cool for 2 hours on a wire rack, then cover loosely with plastic wrap and chill overnight.
2. Make the Pineapple Cake (Day Of)
Prepare the topping:
Spray a 9-inch cake pan with nonstick spray. Melt brown sugar and butter in a saucepan until combined. Pour into the pan and tilt to coat the bottom.
Pat pineapple slices and cherries dry with a paper towel. Arrange pineapple slices in the caramel sauce and place cherries in the centers (cut-side up if halved).
Make the cake batter:
Melt 5 tbsp butter in a bowl. Stir in sugar. Whisk in eggs, then add buttermilk, baking powder, vanilla, salt, and baking soda. Stir in flour until just combined (do not overmix).
Gently spread the batter over the fruit layer.
Bake:
Bake at 350°F for 30 minutes. Let rest for 1 minute in the pan.
Place a rimless baking sheet upside down over the cake pan and carefully invert. Let cool completely.
3. Assemble the Cheesecake
Remove the cheesecake from the springform pan, leaving the base attached. Place it on a serving platter.
Using a large spatula and steady hands, carefully lift the cooled pineapple upside-down cake and slide it onto the top of the cheesecake.
Optional: Drizzle with extra caramel sauce and decorate with more cherries.
Serving & Storage
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Slice with a sharp knife, wiping between cuts for clean slices.
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Store covered in the fridge for up to 4 days.
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Best served chilled or at room temperature.
Final Thoughts
This Pineapple Upside-Down Cheesecake is the kind of dessert people remember. Moist vanilla cake, glossy pineapple and cherry topping, and a thick, luscious layer of cheesecake? It’s everything you love in one dreamy bite.