A stunning mashup of two beloved classics — the fruity caramel goodness of a pineapple upside-down cake combined with the creamy indulgence of a cheesecake.
This Pineapple Upside-Down Cheesecake isn’t just a dessert — it’s the centerpiece of any gathering. Sweet, tangy pineapple slices caramelized in brown sugar sit atop a luscious cheesecake layer, all balanced by a soft vanilla cake.
If you’re looking to wow your guests or treat yourself, this is the recipe you need in your collection!
Why You’ll Love This Recipe
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A Beautiful Dessert with Impressive Layers
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Sweet, Tangy, and Perfectly Creamy
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Ideal for Special Occasions or Holidays
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Make-Ahead Friendly — Best Served Chilled
Ingredients
For the Pineapple Topping:
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¼ cup unsalted butter, melted
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½ cup packed brown sugar
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6–8 pineapple rings (canned or fresh)
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Maraschino cherries (optional, for decoration)
For the Cheesecake Layer:
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2 (8 oz) packages cream cheese, softened
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¾ cup granulated sugar
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2 large eggs
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1 teaspoon vanilla extract
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½ cup sour cream
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¼ cup pineapple juice (from canned pineapple or fresh)
For the Cake Layer:
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1½ cups all-purpose flour
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1½ teaspoons baking powder
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¼ teaspoon salt
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½ cup unsalted butter, softened
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¾ cup granulated sugar
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2 large eggs
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1 teaspoon vanilla extract
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½ cup whole milk
How to Make Pineapple Upside-Down Cheesecake
Step 1: Preheat the Oven
Preheat your oven to 350°F (175°C).
Grease a 9-inch springform pan and line the bottom with parchment paper.
Step 2: Prepare the Pineapple Topping
Pour the melted butter into the bottom of the pan.
Evenly sprinkle the brown sugar over the butter.
Arrange the pineapple rings on top and place a maraschino cherry in the center of each ring if using. Set aside.
Step 3: Make the Cheesecake Layer
In a large bowl, beat the cream cheese and granulated sugar until smooth and creamy.
Add the eggs, one at a time, mixing well after each addition.
Beat in the vanilla extract, sour cream, and pineapple juice until smooth. Set aside.
Step 4: Prepare the Cake Layer
In a medium bowl, whisk together the flour, baking powder, and salt.
In another bowl, beat the butter and sugar until light and fluffy.
Add the eggs, one at a time, beating well after each addition. Stir in the vanilla.
Gradually add the dry ingredients and milk, alternating between the two, beginning and ending with the dry ingredients. Mix until just combined.
Step 5: Assemble the Cheesecake
Pour the cheesecake batter gently over the arranged pineapple slices.
Carefully spoon the cake batter over the cheesecake layer and smooth the top.
Step 6: Bake
Place the springform pan on a baking sheet to catch any potential drips.
Bake for 60–70 minutes, or until the cake is golden and a toothpick inserted in the center comes out clean.
Step 7: Cool and Invert
Let the cake cool in the pan for 15 minutes.
Run a knife around the edges, then carefully invert onto a serving plate.
Peel away the parchment paper gently.
Step 8: Chill
Allow the cake to cool completely.
Refrigerate for at least 4 hours or overnight to fully set the cheesecake layer.
Serving Suggestions
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Serve chilled for a firmer texture or at room temperature for a creamier bite.
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Garnish with whipped cream or extra maraschino cherries for an eye-catching finish.
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Pairs wonderfully with a hot cup of coffee or a tropical fruit cocktail.
Final Thoughts
This Pineapple Upside-Down Cheesecake is everything a dessert should be — beautiful, indulgent, and unforgettable.
With layers of tangy fruit, creamy cheesecake, and soft vanilla cake, every bite is a perfect combination of flavors and textures.
Bake it for your next celebration, and watch it disappear slice by slice!