Pineapple Upside Down Cheesecake

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Ingredients

For the crust:
    • 1 1/2 cups graham cracker crumbs
    • 1 Tablespoon sugar
    • 6 Tablespoons melted butter (either salted or unsalted works fine here)
For the cheesecake:
    • Four 8 ounce packages cream cheese (we use Philadelphia Cream Cheese), room temperature
    • 1 2/3 cup sugar
    • 1/4 cup cornstarch
    • 1 Tablespoon vanilla
    • 2 extra large eggs
    • 3/4 cup heavy cream
For the cake:
  • 1 (20 ounce) can pineapple slices in juice, drained
  • 1/2 cup brown sugar
  • 4 Tablespoons salted butter
  • maraschino cherries, 7 or so depending upon your design
  • 5 Tablespoons salted butter
  • 2/3 cup sugar
  • 2 large or extra large eggs
  • 1/2 cup buttermilk
  • 1 teaspoon baking powder
  • 1 teaspoon vanilla extract
  • 1/4 teaspoon salt
  • 1/4 teaspoon baking soda
  • 1 1/4 cups all purpose flour
  • Extra cherries and warmed caramel sauce for serving, see notes for recipe links

Instructions

  1. The day before you want to serve the cake, make the cheesecake.
  2. Preheat oven to 350 degrees F. Prepare a 9″ springform pan by wrapping the bottom and sides with heavy aluminum foil. This is to insure that nothing in your pan leaks out and that water won’t get into your pan when the cheesecake bakes.
  3. Combine graham cracker crumbs, sugar and melted butter. Pour into a 9″ springform pan and using your hands or the bottom of a glass, press the crumbs on the bottom and up the sides about a half inch or so. (My husband/kids only pressed on the bottom, so that’s what you see in the photos. Either way is fine.)
  4. Bake crust for 8 minutes and set aside to cool.
  5. Make the filling. In a large bowl, with an electric mixer (use paddle attachment for stand mixers), beat one package of the cream cheese, 1/3 cup of the sugar and the cornstarch together on low until creamy, about 3 minutes. Scrape down the sides of the bowl as necessary.
  6. Blend in the remaining cream cheese, one package at a time, beating well after each addition.
  7. Increase the mixer speed to medium and beat in the remaining 1 1/3 cups sugar, then the vanilla.
  8. Blend in the eggs, one at a time, beating well after each.
  9. Beat in the cream just until completely blended. The mixture should look light, creamy and billowy. Be careful not to over mix at this step.
  10. Place the pan in a large shallow baking dish (we used a roasting pan) and pour in hot water until it comes up about halfway, (about 1 inch), up the side of the baking pan. Be careful not to splash any water into your cheesecake while you’re pouring.
  11. Carefully transfer pan to oven. Bake until light golden brown and the center barely jiggles, about 1 hour and 15 minutes.
  12. Remove the cheesecake from the water bath and allow to cool on a rack for 2 hours. Cover top of pan loosely with plastic wrap and chill overnight in the refrigerator.
  13. The day of serving, make the cake.
  14. Preheat oven to 350 degrees F. Spray a 9″ cake pan with cooking spray.
  15. Melt the 1/2 cup brown sugar and 4 Tablespoons of butter in a small sauce pan until sugar dissolves and mixture has fully combined. Do not cook or bring to a boil. You just need the sugar and butter to melt and combine. Remove from heat and pour into the prepared cake pan, tilting it back and forth to cover the entire bottom evenly.
  16. Decide how you want to arrange your pineapples and cherries. We used 7 pineapple rings (some cut in half) and 13 cherry halves for our design. You don’t have to cut your cherries, you may leave them whole, if you wish. Once you figure out how many pieces of fruit you need for your design, pat them all dry with paper towels, then arrange them in the pan on top of the caramel sauce layer. If your cherries are cut in half, place them into the pan, cut side up so that the uncut side will be on top when you flip your cake over.
  17. Make the cake batter. Melt the 5 Tablespoons of butter in a large microwave safe bowl. Cover and microwave on high for 1 minute or until butter is melted. Add sugar, stirring with a whisk. Add eggs and whisk to combine.
  18. Whisk in buttermilk and next four ingredients (buttermilk through baking soda.)
  19. Add flour and stir just until blended (do not over stir.) Carefully pour the batter into the pan on top of the fruit layer.
  20. Bake at 350 degrees F. for about 30 minutes or until a toothpick comes out clean.
  21. Cool for 1 minute in pan. Place a baking sheet with no rim (or flip it so that you have a flat surface) upside down on top of the cake pan and invert the cake onto the plate. Cool completely.
  22. To assemble, remove chilled cheesecake from refrigerator and remove the sides of the springform pan. Leave the cake on the bottom of the springform pan for serving. Place the cake on serving plate, then using a large spatula, lift and slide the cooled pineapple cake off the pan and onto the top of the cheesecake. (You need the no rim sheet/plate so that you can easily slide the cake off of it. I used a cake lifter, but the pan should work fine)
  23. Slice and serve with warm caramel sauce and extra cherries, if desired.

Notes

*For the pineapple upside down cake, you could use 1/3 to 1/2 cup of prepared caramel sauce instead of melting the brown sugar and butter together. The original light recipe calls for 1/3 cup of fat free caramel topping drizzled in the bottom of the pan. The homemade version makes the fruit sink in a bit more, but I don’t mind that at all and the flavor is so much better.

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