Homemade Pineapple Upside Down Cheesecake Recipe - Restless Chipotle (2024)

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.

🗝️ Key takeaways

• This recipe is so easy! No need to invert cheesecake - the topping is done separately!
• The gooey, syrupy rum topping is just like your favorite part of Mom's pineapple upside-down cake—so much nostalgia!
• Serve this for any special occasion or when you are craving something delicious.
• The cheesecake layer should be creamy and smooth. Use room-temperature cream cheese for easier mixing and to avoid lumps. Incorporating eggs one at a time and mixing on a low speed can help achieve a smooth batter.

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!

🧾 Ingredients

• 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 co*ke 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.

📖Variations

• 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 instead of the vanilla in the cheesecake filling.
• 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.
• Cut up fresh pineapple and strawberries for a fresh pop of flavor and use them instead of the canned pineapple.
• Try drizzling the top with melted white chocolate just before serving.

🔪 Instructions

This is an overview of the instructions. Full instructions are in the green recipe card at the bottom of the page.

1. Press the crust in the bottom of the springform pan.
2. Beat filling ingredients on the lowest setting and spoon the cream cheese mixture into the pan. Bake as directed.
3. Make glaze and spoon over the cooled cake. Arrange pineapple rings on the top, then place cherries in the centers of pineapple slices. Add pecans.

🥫 How to store leftovers

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.

💭 Things to know

• 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. you don't want to whip air into your filling. Use the paddle attachment(s) to blend the ingredients together on the mixer's low speed.
• Always let the 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.

👩‍🍳 FAQs

• 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.

📞 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.

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

📖 Recipe

First published July 20, 2013. Last updated February 16, 2024 for readability.

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