pineapple upside down cake top
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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.
Course Dessert - Cake
Cuisine Amercian Heritage
Keyword cream cheese, maraschino cherries, pecans, pineapple
Prep Time 10 minutes
Cook Time 45 minutes
Resting time 1 hour
Total Time 8 hours 55 minutes
Servings 16 servings
Calories 541kcal
Author Marye Audet-White




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


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



  • 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.


  • Always have all ingredients at room temperature unless otherwise directed.
  • Don't whip the filling. Use the paddle attachment to blend the ingredients together on low speed of your mixer.
  • Let come to room temperature before chilling.
  • Make it a day ahead of time so it can chill overnight in the refrigerator.
  • Place folded paper towels lightly on top of the cake before covering with plastic wrap and chilling. They'll soak up any moisture that forms.
  • Run a warm knife between the edge of the cheesecake and the inside of the pan to loosen it before removing the sides.
  • If the top does happen to crack just make a glaze and add a topping. For a plain cheesecake cherry or blueberry pie filling works beautifully to cover up imperfections!
  • May be made up to two days ahead and refrigerated, tightly covered.


Calories: 541kcal | Carbohydrates: 52g | Protein: 6g | Fat: 35g | Saturated Fat: 19g | Cholesterol: 95mg | Sodium: 354mg | Potassium: 221mg | Fiber: 1g | Sugar: 45g | Vitamin A: 1163IU | Vitamin C: 4mg | Calcium: 111mg | Iron: 1mg