There’s something magical about the combination of caramelized pineapple, sweet cherries, and creamy cheesecake—it’s the perfect balance of indulgence and nostalgia.
This Pineapple Upside Down Cheesecake takes the iconic retro dessert and gives it a decadent upgrade. Imagine the buttery, golden pineapple topping you love, paired with velvety cheesecake and a hint of brown sugar glaze in every bite.
I first made this recipe on a whim during a summer barbecue, craving something that screamed “sunshine.” Alongside this cheesecake, I served a warm Cornbread Casserole, and the combo was pure comfort food bliss.
To my delight, the cheesecake stole the show, with its layers of tangy pineapple and creamy cheesecake bringing everyone back for seconds.
Bonus: it’s surprisingly easier to make than you’d think, much like a quick Navajo Fry Bread, thanks to simple techniques like layering the fruit directly in the pan before pouring in the batter.
This dessert is trending because it combines two beloved classics in one show-stopping dish, offering the tropical vibes we all crave.
Why You’ll Be Hooked?
- Irresistible Layers of Flavor: The contrast between buttery caramelized pineapple and creamy cheesecake is a match made in dessert heaven.
- Easy Crowd-Pleaser: Whether for a backyard party or a holiday table, this dessert always gets rave reviews.
- Customizable Fun: I’ve swapped out cherries for maraschino raspberries, and the results were just as stunning.
- Summery Vibes Year-Round: Even in the dead of winter, one bite brings back those warm, sunny feelings.
- A Baking Confidence Boost: This recipe is more forgiving than it looks—perfect for both beginners and seasoned bakers.
Pineapple Upside Down Cheesecake Recipe
Equipment
- 9-inch springform pan
- 10-inch skillet
- Mixing Bowls
- Hand
- Spatula
- Saucepan
- Measuring Cups
Ingredients
Pineapple Compote
- 6 cups pineapple rings quartered, with juice drained & reserved This equates to 3 cans of pineapple rings 1074 grams of pineapple
- 1 and 1/4 cups pineapple juice
- 2/3 cup + 1 tbsp dark brown sugar packed 300 grams
- 2 tbsp + 1 tsp corn starch
- 2 tbsp + 1 tsp water
- 2 tsp vanilla extract
- 2-3 tbsp vanilla rum or coconut rum optional
For the Crust:
- 3 cups graham cracker crumbs 276 grams
- 1/2 cup salted butter melted 113 grams
- For the Cheesecake Batter
- 32 ounces full fat cream cheese softened at room temperature 906 grams
- 1 and 1/2 cups brown sugar 330 grams
- 4 large eggs at room temperature
- 3/4 cup full fat sour cream at room temperature 180 grams
- 2 tsp vanilla extract
For the Whipped Cream
- 4 tsp cold water
- 1 tsp plain powdered gelatin This is available in the baking aisle of most grocery stores
- 1 cup heavy whipping cream
- 1/4 cup + 2 tbsp powdered sugar
- 2 tsp vanilla extract
For Decorating:
- maraschino cherries
Instructions
- Make Pineapple Filling: Cook pineapple, brown sugar, and juice until syrupy, then thicken with cornstarch slurry. Cool completely.
- Prepare Crust: Preheat oven to 350°F, mix graham crumbs with melted butter, press into a springform pan, and bake for 10 minutes.
- Make Cheesecake Filling: Beat cream cheese and sugar, add eggs one at a time, then mix in vanilla, sour cream, and optional rum.
- Set Up Water Bath: Boil water and place the springform pan inside a 10-inch pan, then both inside a roasting pan.
- Assemble Cheesecake: Layer half the cheesecake batter, pineapple filling, and remaining batter in the crust.
- Bake Cheesecake: Bake in the water bath for 1 hour 25 minutes to 1 hour 45 minutes, then cool in the oven for 1 hour.
- Chill Cheesecake: Refrigerate for at least 6 hours or overnight.
- Make Stabilized Whipped Cream: Beat cream with sugar and vanilla, adding liquified gelatin until stiff peaks form.
- Serve: Top cheesecake with pineapple, pipe whipped cream, garnish with cherries, and enjoy!
