Pineapple Upside Down Cheesecake

  • Total:2 hrs
  • Prep:30 mins
  • Cook:90 mins
  • Chill Time:3 hrs
  • Yield:1 cake (serves 16)

This recipe has everything you love about a classic pineapple upside down cake in the rich, creamy form of a decadent cheesecake!

The cheesecake starts with a traditional graham cracker crust that is filled with a cream cheese batter. When it comes out of the oven, that’s when things get really exciting. A can of pineapple slices in heavy syrup is drained and used to create a topping for the cheesecake. Then the pineapple rings are arranged like a typical upside down cake, with maraschino cherries inside each ring. The result is a stunning dessert that looks like it came from a restaurant or bakery.


  • For the Cheesecake:
  • 1 1/3 cups graham cracker crumbs
  • 1 1/2 cups sugar
  • 1/4 cup (1/2 stick) butter (melted)
  • 3 (8-ounce) packages cream cheese (room temperature)
  • 2 tablespoons flour
  • 3 eggs
  • 1 egg yolk
  • 2 teaspoons vanilla
  • 3 tablespoons heavy cream
  • For the Topping:
  • 1 (20-ounce) can pineapple slices in heavy syrup
  • 1 packet unflavored gelatin
  • 2 tablespoons orange juice or water
  • 8 maraschino cherries

Steps to Make It

  1. Gather the ingredients.
  2. Make the crust. Combine the graham cracker crumbs, 1/4 cup of the sugar, and melted butter.
  3. Press the mixture evenly on the bottom and halfway up the side of a lightly buttered 9-inch springform pan. Chill while preparing the next steps.


    When making cheesecakes, line the springform pan with foil to prevent leaks.

  4. Make the cheesecake filling. Beat the cream cheese in a large bowl until smooth; blend in 1 1/4 cups of the remaining sugar, and the flour. Beat with an electric mixer until light and fluffy. 
  5. Add the eggs and egg yolk, 1 at a time, beating well after each addition. Stir in the vanilla and cream.
  6. Pour into the prepared crust and smooth the top. Bake in a 450 F oven for 10 minutes. Lower temperature to 250 F and bake 1 hour and 20 minutes longer. 
  7. Remove cake from the oven and cool completely on a wire rack. 
  8. Make the topping. Drain the juice from the can of pineapple slices into a small bowl. Set aside pineapple slices. 
  9. In a small saucepan, combine the reserved syrup from the can of pineapples with the orange juice or water. Sprinkle gelatin over the juices to soften, about 5 minutes. Heat over very low heat, stirring often, until gelatin clears and dissolves. Chill until syrupy but not set.
  10. Cut 4 of the reserved pineapple slices in half and arrange around the edge on top of cake. Place one whole pineapple ring in the center. (Reserve remaining pineapple slices for another use.)
  11. Spoon the chilled pineapple topping over to cover the center of the cake. Place maraschino cherries in the center of each pineapple ring. 
  12. Chill for at least three hours or until topping is set. Remove the side of the springform pan before slicing and serving.
  13. Enjoy!

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