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 pineapple flavor.
❤️ Why you'll love it
- Decadently creamy with tons of tropical flavor!
- A perfect homemade cheesecake with easy-to-follow steps.
- The gooey, syrupy rum topping is just like your favorite part of Mom's pineapple upside-down cake—so much nostalgia!
This pineapple upside-down cheesecake is the ultimate update on everyone's most-loved classic recipe. From the crunchy graham cracker crust to the sweet, sticky pineapple rings and cherries on top, this is THE cheesecake recipe to remember. After all, your family and friends will!
- 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 or raw sugar. The crystals are too big.
- 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 or fat-free. I use Philadelphia Brand.
- 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.
- 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.
This is an overview of the instructions. Full instructions are in the green recipe card at the bottom of the page.
- Press crust in the bottom of the springform pan.
- Beat filling ingredients on lowest setting and spoon cream cheese mixture into pan. Bake as directed.
- Make glaze and spoon over cooled cake. Arrange pineapple rings on the top, then place cherries in the centers of pineapple slices. Add pecans.
Cheesecake should be refrigerated at all times. It'll last sealed in an airtight container (or covered tightly with plastic) for two days.
Serve chilled, or let it sit at room temperature for a few minutes before digging into your leftovers!
While plain, creamy cheesecake can be frozen, the fruit topping doesn't handle it as well. For best results, I'd recommend against freezing leftover pineapple upside down cheesecake.
- Graham crackers are used for the crust because they perfectly complement the brown sugar in the sticky syrup. However, you could also use crushed 'Nilla wafers or butter cookies.
- Pecans are my favorite topping for this cake, but you could use walnuts or macadamia nuts... if you must. Toast the nuts before using them for an extra crunch and a more buttery flavor.
- To amp up the tropical flavor, use coconut extract in place of the vanilla.
- If you don't love pineapple, consider using sauteed apples or mango in place of the pineapple rings, and apple cider in place of the pineapple juice. In that case, I'd also omit the cherries.
- For a fresh pop of flavor, cut up fresh pineapple and fresh strawberries and use them instead of the canned pineapple.
- Try drizzling the top with melted white chocolate just before serving.
💭 Things to know
Expert Tip: Ingredients matter! Don't swap for even minor changes if at all possible. Use a good quality butter, full-fat cream cheese and sour cream, large, fresh eggs, and a good vanilla extract (or vanilla bean paste.)
- Plan to make the pineapple upside-down cheesecake a day ahead of time so it can chill overnight in the refrigerator for best results.
- Always let all ingredients come to room temperature before baking with them unless otherwise directed.
- Don't whip the filling, or it could start to separate! Use the paddle attachment(s) to blend the ingredients together on the mixer's low speed.
- Always let cheesecake come to room temperature before chilling. After all, you should never put a hot dish straight into the fridge.
- You can place folded paper towels lightly on top of the cake before covering it with plastic wrap and chilling. They'll soak up any moisture that forms and keep the top of the cheesecake from getting soggy.
- To prevent any breaking, run a warm knife between the edge of the cheesecake and the inside of the spring-form pan to loosen it before removing the sides.
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.
A water bath helps create a steamy environment for the cheesecake and protects it from drastic changes in temperature. This prevents cracking and falling. It is also why all of my cheesecake recipes call for you to add the springform pan to a bigger pan of water during baking.
Don't worry, it's pretty simple! First, wrap the outside (including the bottom) of the springform pan in foil to help protect it from water leaking into the pan.
Next, place the pan in a larger pan (I use a roasting pan) and pour hot water into the bigger pan until it is halfway up the sides of the springform. Try to go slowly so you don't splash any water into the cheesecake batter. Finally, carefully put it in your preheated oven and bake according to your recipe.
Nope! You can bake it in a regular cake pan. Grease the pan well with butter or non-stick spray and add a layer of parchment paper that extends over the sides. Then, add the crust and the cheesecake batter and bake as directed. Once the cheesecake has set in the refrigerator (four hours or more) use the parchment that's hanging over the sides to lift the cake out and put it on a serving plate.
📚 Related recipes
- The classic, old-fashioned Pineapple Upside Down Cake that everyone knows and loves—with an easy, beginner-friendly recipe!
- No-Bake Lemon Cheesecake is the best when you don't want to heat up the kitchen AND it tastes just like Woolworth's!
- With pieces of moist red velvet cake and a super special red velvet crust, this Homemade Red Velvet Cheesecake is delicious.
🍽️ Serve with...
📞 The last word
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 favorite cheesecake.
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. Don't forget that you can click on "add to collection" to save it to your own, private recipe box!
If you love this recipe please give it 5 stars! ⭐️⭐️⭐️⭐️⭐️
Pineapple Upside Down CheesecakePrint Save Go to Collections
- 2 cups graham cracker crumbs
- ¼ cup sugar
- ⅓ cup butter, melted
- 32 ounces cream cheese, room temp
- 2 cups sugar
- 6 eggs
- 1 ½ teaspoons vanilla
- ¼ cup pineapple juice , reserved from the pineapple slices below
- 16 ounces sour cream
- ¼ cup butter
- ½ cup brown sugar
- 2 tablespoons spiced rum
- 20- oz can pineapple slices in juice, drained and ¼ cup juice reserved
- 12 oz jar maraschino cherries, you'll need 9 or 10 drained and patted dry
- ½ cup pecans
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- 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.
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First published July 20, 2013. Last updated July 3, 2022 for readability.
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Penny S. Underwood
Your recipe calls for spiced rum, but in the instructions for the topping it states to add bourbon. Which one do I use?
Either is fine.
Kimberly @ The Daring Gourmet
Nice! I've had pineapple upside-down cakes but never cheesecakes - great idea!
Shashi @ RunninSrilankan
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!
Michelle | A Dish of Daily Life
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!
Oh it's so good!
This looks wonderful. I need to try to make this for my husband. He loves cheesecakes!
Let me know what he thinks. 🙂
This looks fantastic! Thanks for sharing!
Citra Kale @Citra's Home Diary
I love pineapple upside down cake.. and you twist the pineapple with cheesecake...hmmm that's even combo Merye..
Thank you so much!
allie @ Through Her Looking Glass
Dear Marye, all your cakes are gorgeous. This is no exception. The graham cracker crust is perfection, as is the rum syrup!!!!
Thank you Allie!
Kacey @ The Cookie Writer
Wonder Bread was a staple of ours growing up! Love this spin on a classic dessert. Plus, I love making cheesecakes so this is just another excuse for me 🙂
Oh I do too!
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!
Your pan may be thicker? Yeah, try baking it 5 to 10 minutes longer and see if that helps.
Katie @ Recipe for Perfection
Oh, this is just a beautiful combination! I love pineapple upside down anything!
Erica @ The Crumby Cupcake
Please, go ahead and make one of my favorite desserts of all time even more decadent, why don't you??? LOVE this idea, and the caramelized pineapple on top looks perfect!
Love that you did a cheesecake instead of a regular upside down cake. What a great way to update a classic.