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Pineapple Upside Down Cheesecake

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This pineapple upside down cheesecake is decadently rich and luscious. Creamy pineapple cheesecake is topped with juicy pineapple rings, cherries, and pecans in a brown sugar glaze. The easy graham cracker crust doesn’t get in the way of all of those flavors and textures, either! Not quite what you’re looking for? Check out my 50 Best Cheesecakes!

For this recipe you’ll need: graham crackers, sugar, butter, cream cheese, pineapple rings in pineapple juice, eggs, vanilla, sour cream, brown sugar, spiced rum, maraschino cherries, pecans, a deep 9-inch springform pan or a 10-inch springform pan, aluminum foil, larger pan for water bath
homemade pineapple upside down cheesecake

Pineapple upside down cake is an iconic dessert that probably represents the 1950s and 1960s  as much as Wonder Bread does. Personally, I’d rather have the cake. I wanted to try to do a spin on the original with cheesecake — y’all know that cheesecakes are something I love to make! I knew that turning the cake upside down wasn’t going to work but I wanted that same syrupy, gooey topping with big bursts of pineapple flavor.

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I thought about it a lot and finally decided on a pineapple-vanilla flavored cheesecake with the pineapple and cherries and pecans just like the cake. After my dismal failure using lemon cake as a base for my lemon meringue pie cheesecake I chose to stick with a graham cracker crust for this. It works well because the graham mirrors that brown sugar in the topping.

close up of pineapple topping on cheesecake

 

Doncha just want to lick your computer screen right now?

The filling is that dense, rich, New York style cheesecake that I love. It has just a hint of pineapple flavor so it doesn’t become overpowering, you know? I wanted to be able to taste the brown sugar, the pecans, the burst of cherry… Just a minute, have to wipe my mouth.

Anyway, I have three springform pans and I was using the 9-inch pan for the s’mores cheesecake. I used a 10-inch pan for this, which made it a bit thinner, as you can see. I actually think I prefer it this way because it looks more like the splendiferous dessert it was named for.

slice of homemade pineapple upside down cheesecake

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This leakproof springform pan is the exact one I use. I love the way it’s lipped on the bottom and (of course) it comes in RestlessChipotle red!

Pineapple Upside Down Cheesecake Recipe

If you crave pineapple upside down cake then you will absolutely love this cheesecake version. It’s sweet, rich, and creamy with a ton of tropical flavor. If you like this recipe please give it 5 stars!

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5 from 1 vote

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 Time5 hrs 10 mins
Cook Time45 mins
Total Time5 hrs 55 mins
Servings: 16 servings
Calories: 596kcal
Author: Marye

Ingredients

Crust

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

Cheesecake

  • 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

Topping

  • 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

Instructions

Crust

  • 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.

Cheesecake

  • 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.

Topping

  • 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.

Notes

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

Nutrition

Calories: 596kcal | Carbohydrates: 61g | Protein: 7g | Fat: 36g | Saturated Fat: 19g | Cholesterol: 156mg | Sodium: 359mg | Potassium: 234mg | Fiber: 1g | Sugar: 53g | Vitamin A: 25.2% | Vitamin C: 4.8% | Calcium: 13.1% | Iron: 7.4%

If you liked this pineapple upside down cheesecake recipe you may also like…

From left to right:  Basic New York Style Cheesecake, Irish Cream Cheesecake, Pumpkin Cheesecake with Gingersnap Crust

basic new york style cheesecake  irish cream cheesecake  pumpkin cheesecake

OTHER CHEESECAKES YOU MIGHT LIKE…

Caramel Apple Crisp Cheesecake Cakes Cottage

Salted Caramel Cheesecake Ashlee Marie

Comments

  3. Now I have had pineapple -upside down cake before – but never pineapple upside down cheesecake – wow – this is amazing! My salivary glands are in overproduction at that crust and brown sugared pineapple topping and cheesecake together!

    Reply

  4. This is an absolute match made in heaven!! I can’t tell you how much I love pineapple upside down cake and then you go and pair it with another big fave, cheesecake?! I am wishing I could grab a slice right off the screen right now, Marye!

    Reply

  10. I have made your Pineapple Upside Down Cheesecake 3 times and each time the center is not set. I follow the recipe exactly as written. I feel like I should maybe bake it longer? Need help!

    Reply

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