Pineapple Upside Down Cheesecake

If you love cheesecake and pineapple upside-down cake, then this recipe is a must-try! It starts with my favorite cheesecake, inspired by the famous Junior’s. After allowing the cheesecake to chill completely, I even make it two days ahead because it holds up so well! Then, I prepare the pineapple upside-down cake and let it cool at room temperature before placing it directly on top of the cheesecake. It’s a perfect fit. Chill it overnight and serve straight from the fridge for absolute perfection. This dessert is great because you can prepare it days in advance. Feel free to enjoy just the pineapple upside-down cake without the cheesecake, too!

Why You’ll Love This Recipe

This Pineapple Upside Down Cheesecake combines the rich creaminess of cheesecake with the sweet, fruity flavors of pineapple and cherries. It’s a show-stopping dessert that’s perfect for any occasion. Plus, you can make it ahead of time, so it’s stress-free on the day of your event!

Kitchen Equipment You’ll Need

• 9-inch springform pan
• 9-inch cake pan
• Electric mixer with paddle attachment
• Large shallow pan for water bath
• Wire rack
• Large spatula

Ingredients

Cheesecake Crust:

• 1 1/2 cups graham cracker crumbs
• 1 tablespoon sugar
• 6 tablespoons melted butter

Cheesecake Filling:

• Four 8-ounce packages PHILADELPHIA cream cheese, at room temperature
• 1 ⅔ cups sugar
• ¼ cup cornstarch
• 1 tablespoon pure vanilla extract
• 2 extra-large eggs
• ¾ cup heavy whipping cream

Pineapple Upside Down Cake Topping:

• ¼ cup butter, melted
• ½ cup packed light brown sugar
• 8 canned pineapple slices
• 15-20 maraschino cherries

Pineapple Upside Down Cake:

• 1 and ⅔ cups flour
• ½ teaspoon baking powder
• ¼ teaspoon baking soda
• ½ teaspoon salt
• ½ cup butter, melted
• ¾ cup packed light brown sugar
• ¼ cup granulated sugar
• 1 large egg
• ¾ cup milk
• ½ cup pineapple juice
• 1 tablespoon vanilla

Step-by-Step Instructions

For the Cheesecake Crust:

1. Combine the graham cracker crumbs, sugar, and melted butter. Press into a 9-inch springform pan.

2. Bake at 350°F for 8 minutes and let cool.

For the Cheesecake Filling:

1. In a large bowl, use an electric mixer with the paddle attachment to beat 1 package of cream cheese, ⅓ cup of sugar, and cornstarch on low until creamy, about 3 minutes. Scrape down the bowl several times.

2. Blend in the remaining cream cheese, one package at a time, beating well and scraping down the bowl after each addition.

3. Increase the mixer speed to medium and beat in the remaining sugar and vanilla.

4. Blend in the eggs, one at a time, beating well after each.

5. Beat in the cream until completely blended. The filling should look light and airy.

6. Gently spoon the batter over the crust. Wrap the sides of the pan in aluminum foil.

7. Place the cake pan in a large shallow pan filled with hot water, reaching halfway up the sides of the springform pan. Bake for about 1¼ hours, until the edges are light golden brown and the center barely jiggles.

8. If the edges are still soft, bake for an additional 10 minutes.

9. Remove from the water bath, transfer to a wire rack, and let cool for 2 hours. Chill until cold.

For the Pineapple Upside Down Cake:

1. Preheat oven to 350°F.

2. For the topping, place ¼ cup of melted butter into a 9-inch cake pan. Sprinkle with brown sugar. Arrange pineapple slices and cherries on top.

3. In a microwave-safe bowl, melt the butter for the cake batter. Whisk in both sugars.

4. Whisk in the egg, milk, pineapple juice, and vanilla.

5. Add dry ingredients and whisk to remove lumps. Pour the batter over the pineapple topping in the pan.

6. Bake for 20 minutes, then loosely tent with foil to prevent browning. Bake an additional 20-25 minutes until a toothpick comes out clean.

7. Cool for 10 minutes and invert onto a large plate.

8. Once cool, use a large spatula to transfer the cake on top of the cheesecake. Chill until cold.

Tips for Success

• Use room temperature ingredients for a smoother cheesecake filling.
• Be gentle when mixing the cheesecake batter to avoid overmixing.
• Ensure your springform pan is properly sealed to prevent water from seeping in during the water bath.

Additional Tips and Variations

• Try adding a splash of rum to the pineapple juice for a tropical twist.
• For a nutty flavor, consider adding crushed pecans or walnuts to the crust.

Nutritional Highlights (Per Serving)

Calories: 500 | Fat: 30g | Carbohydrates: 55g | Protein: 8g | Sugar: 38g

Frequently Asked Questions (FAQ)

Can I make this dessert ahead of time?

Yes! This dessert can be made a few days in advance and stored in the refrigerator until ready to serve.

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple will work just as well, although it may alter the sweetness slightly.

What if I don’t have a springform pan?

You can use a regular cake pan, but make sure to line it with parchment paper for easier removal.

Conclusion

This Pineapple Upside Down Cheesecake is a delightful fusion of two classic desserts. Its rich and creamy texture, combined with the sweet and tangy pineapple topping, is sure to impress your guests. I invite you to try this recipe and share your experiences in the comments below. Enjoy every delicious bite!