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 choices for the 50 Best Cheesecakes!

Pineapple Upside Down Cheesecake Ingredients

So many of the pineapple upside down cheesecake recipes that I’ve seen are cakes with cheesecake in the center. I didn’t want that because, like Brooke Shields and Calvin Klein jeans, I didn’t want anything to get between me and my cheesecake.

So, I kept it simple.

• Graham crackers are used for the crust but you could also use ‘Nilla wafers or butter cookies.
• Sugar used is just plain, old granulated sugar. Don’t use anything, like turbinado, that has big crystals.
• Butter plays a major role in the flavor so get a good one. Some of the off brands can have off flavors. I use Kerrygold.
• Cream cheese is also very important! Use regular cream cheese not low fat. I use Philadelphia Brand. Make sure it’s fresh and keep it refrigerated.
• Pineapple rings in pineapple juice only. Make sure you don’t get the kind in syrup because you’ll be needing the juice. Plus they’re too sweet.
• Eggs used are large, pasture raised, organic. Ok – I know the eggs aren’t pasture raised but the chickens are.
• Vanilla softens the flavors and brings them all together like a 1970’s Coke commercial.
• Sour cream should be the real deal. Don’t use low fat, fat free, or Greek Yogurt here. I use Daisy Brand.
• Brown sugar is what makes the glaze. You can use dark or light brown – whichever you like best.
• Spiced rum can be omitted but it’s awfully good.
• Maraschino cherries add a pretty color and what’s a pineapple upside down cake without them?
• Pecans are my favorite but you could use walnuts… if you must. Toasting the nuts before using them gives them extra crunch and a more buttery flavor.

You’ll also need a 10-inch or a deep 9-inch springform pan, aluminum foil, and a large pan for the springform to fit in. I use a roasting pan.

Update on an Iconic Dessert

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.

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.

Thinner Is Better

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.

Pineapple Upside Down Cheesecake FAQs

Here are the most commonly asked questions about this recipe. If you don’t find the answer to yours here leave a comment below or email me – I’ll get back to you as soon as I can!

How do I keep my cheesecake from falling or cracking?

A water bath! This is why all of my recipes call for you to add the pan to a bigger pan of water during baking.

How do you bake cheesecake in a water bath?

1. Wrap the outside (including the bottom) of the springform pan in foil to help protect from water leaking into the pan.
2. Place the pan in a larger pan – I use a roasting pan – and pour hot water in the bigger pan until it is halfway up the sides of the springform pan.
3. Put it in your preheated oven and bake according to your recipe.

Can a cheesecake be baked without a springform pan?

Yes. You can bake it in a regular cake pan.

• Grease the pan well and add a layer of parchment that extends over the sides.
• Add the crust and the cheesecake batter and bake.
• Remove from oven and let cool to room temperature.
• Chill in the refrigerator for 4 hours or more.
• Use the parchment that’s hanging over the sides to lift the cake out and put it on a serving plate.

Tips for Success

Cheesecake are scary and intimidating but they are one of the easiest things to make if you follow some guidelines. Here’s how to get a perfect pineapple upside down cheesecake!

• 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!

More Great Cheesecake Recipes

Cheesecakes are some of my favorite desserts to make and to eat!

Southern Banana Pudding Cheesecake

Take Southern banana pudding and a New York Cheesecake and put them together -what do you get? This creamy New York cheesecake with big banana pudding flavor.

Check out this recipe

Plain Cheesecake (New York Style)

Creamy and rich, this luxurious New York style cheesecake comes out a perfect balance of tangy and sweet. It’s a great base for any kind of topping or a foundation for fancier cheesecakes.

Check out this recipe

Pumpkin Cheesecake with Gingersnap Crust

Creamy and rich, this luxurious New York style pumpkin spice cheesecake comes out perfectly every time! The warm, spicy crunch of the gingersnaps give a nice contrast to the cool, rich flavor of the pumpkin cheesecake. Bourbon is optional but really good!

Check out this recipe

Irish Cream Cheesecake

As rich and creamy as cheesecake gets! This boozy Irish Cream cheesecake is easy to make and absolutely delicious! Flavored with Bailey's and a hint of chocolate.

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Pecan Praline Cheesecake

A rich, dense cheesecake filled with pecans. True praline flavor all the way through.

Check out this recipe

You May Need…

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What’s new? Check out my Restless Chipotle & Co. Store on Amazon where you’ll find all kinds of nostalgic goodness!  Thanks so much for being a part of Restless Chipotle!

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 Variations

This is a great basic recipe with a lot of possibilities for variation. Here are some of my favorites!

• Use coconut flavoring in place of the vanilla
• Sauteed apples in place of the pineapple, apple cider in place of the pineapple juice, and omit the cherries
• Mango in place of pineapple
• Cut up fresh pineapple and cut up fresh strawberries in place of the canned pineapple
• Macadamia nuts instead of pecans
• Drizzle the top with melted white chocolate just before serving
• Butter cookies for the crust
• Try ‘Nilla Wafers for the crust

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 click on the number of servings in the recipe card you can adjust the measurements up or down for the exact number of servings you need.

If you love this recipe please give it 5 stars! ⭐️⭐️⭐️⭐️⭐️

5 from 1 vote

Pineapple Upside Down Cheesecake

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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

Prep Time 10 minutes

Cook Time 45 minutes

Resting time 1 hour

Total Time 8 hours 55 minutes

Servings 16 servings

Calories 541

Author Marye Audet-White

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Equipment Needed

• Stand mixer
• Springform pan

Ingredients

Crust

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

Cheesecake

• 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

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 pecans

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

• 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.

Nutrition

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

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