pineapple upside down cake
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Pineapple Upside Down Cheesecake

Lush cheesecake lightly flavored with pineapple is topped with gooey, spiced rum enhanced syrup, bright pineapple, pecans, and maraschino cherries and then bruleed for just a minute to create an elegant twist on the iconic Pineapple Upside Down Cake.
Prep Time 5 hours 10 minutes
Cook Time 45 minutes
Total Time 5 hours 55 minutes
Servings 16 servings
Calories 596kcal
Author Marye



  • 2 cups graham cracker crumbs
  • 1/4 cup sugar
  • 1/3 cup butter , melted


  • 32 ounces cream cheese , rroom temp
  • 2 cups sugar , room temp
  • 6 eggs
  • 1 1/2 teaspoons vanilla
  • 1/4 cup pineapple juice ,reserved from the pineapple slices
  • 16 ounces sour cream


  • 1/4 cup butter
  • 1/2 cup brown sugar
  • 2 tablespoons spiced rum
  • 20- oz can pineapple slices in juice , drained and 1/4 cup juice reserved
  • 12 oz jar maraschino cherries , you'll need 9 or 10 drained and patted dry
  • 1/2 cup pecan halves



  • Mix the crumbs with the sugar and butter.
  • Press into the bottom and part way up the sides of a 9 inch springform pan.
  • Cover the pan bottom and sides on the outside with aluminum foil to keep any water out.


  • Preheat the oven to 375F.
  • Beat the cream cheese on low speed until smooth.
  • Add the sugar and continue to beat at low speed.
  • Add the eggs, one at a time, beating well after each.
  • Remove bowl from mixer and fold in the vanilla, pineapple juice, and sour cream.
  • Pour into springform and place it in another, larger pan.
  • Add water until it comes halfway up the sides of the outside of the cheesecake pan. (this makes the bain marie)
  • Bake for 45 minutes.
  • Turn off the heat and leave the cake in the oven for 1 hour. DO NOT open the oven door.
  • Remove from the bain marie and to a rack to cool to room temperature.
  • Refrigerate for at least 4 hours or overnight.


  • Remove cake from refrigerator.
  • Run a knife around the edges and carefully remove the sides of the springform pan.
  • Set aside.
  • Melt the butter and brown sugar in a pan, whisking until smooth and most of the graininess is gone.
  • Add the bourbon and whisk smooth over low heat for about 2 minutes.
  • The mixture should be thick and smooth, somewhat like caramel syrup.
  • Remove from heat and let cool until it is just warm to the touch - about 10 minutes.
  • Spoon half of the topping over the cake top.
  • Carefully arrange the pineapple rings, pecans, and cherries over the topping.
  • Spoon the remaining topping over the fruit and use a plumber's torch (or propane kitchen torch) to brulee the top.


May be made up to two days ahead and refrigerated, tightly covered.


Calories: 596kcal | Carbohydrates: 61g | Protein: 7g | Fat: 36g | Saturated Fat: 19g | Cholesterol: 156mg | Sodium: 359mg | Potassium: 234mg | Fiber: 1g | Sugar: 53g | Vitamin A: 1260IU | Vitamin C: 4mg | Calcium: 131mg | Iron: 1.3mg