Pineapple Upside Down Cheesecake

If you love cheesecake and pineapple upside down cake then this is a no brainer! It began with my favorite cheesecake…the one from the famous restaurant Juniors! I let the cheesecake chill completely. I even made it two days before serving because it holds up that well! Then I prepared my pineapple upside down cake. I let it cool at room temp and then transferred it directly on top of the cheesecake! Perfect fit. I chilled that overnight and served straight from the fridge. Perfection. This is such a great dessert because you can prepare it days in advance! Feel free to just use the pineapple upside down cake recipe without the cheesecake too!




1 1 /2 c. graham cracker crumbs

1 T sugar

6 T melted butter


Four 8-ounce packages PHILADELPHIA cream cheese, at room temperature

1⅔ cups sugar

¼ cup cornstarch

1 tablespoon pure vanilla extract

2 extra-large eggs

¾ cup heavy whipping cream




Combine all ingredients and press into a 9 inch springform pan.

Bake at 350 for 8 minutes. Let cool.


In a large bowl, using an electric mixer fitted with the paddle attachment, beat 1 package of the cream cheese, ⅓ cup of the sugar, and the cornstarch together on low until creamy, about 3 minutes, scraping down the bowl several times.

Blend in the remaining cream cheese, one package at a time, beating well and scraping down the bowl after each.

Increase the mixer speed to medium and beat in the remaining sugar, then the vanilla.

Blend in the eggs, one at a time, beating well after each.

Beat in the cream just until completely blended.

The filling will look light, creamy, airy, and almost like billowy clouds. Be careful not to overmix! Gently spoon the batter over the crust. Wrap the sides of the pan in aluminum foil.

Place the cake pan in a large shallow pan containing hot water that comes halfway (about 1 inch) up the side of the springform. Bake until the edge is light golden brown, the top is light gold, and the center barely jiggles, about 1¼ hours. If the cake still feels soft around the edge, let it bake for 10 minutes more (the cooking time will be about the same for both the 8- and 9-inch cheesecakes). Remove the cheesecake from the water bath, transfer to a wire rack, and let cool for 2 hours. Chill until cold.  

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