Pineapple Upside-Down Cheesecake

Pineapple Upside-Down Cheesecake is a delightful twist on two classic desserts: the nostalgic pineapple upside-down cake and the rich, creamy cheesecake. This dessert features a caramelized pineapple and cherry topping, a buttery graham cracker crust, and a smooth, velvety cheesecake filling. Perfect for summer gatherings or special occasions, this recipe will impress your family and friends with its beautiful presentation and delicious flavor.

Ingredients

For the Pineapple Topping:

• 5 tablespoons melted butter
• 2 tablespoons brown sugar
• 2 cans (8 ounces each) pineapple slices, drained
• 7 maraschino cherries, chopped

For the Graham Cracker Crust:

• 1 cup graham cracker crumbs
• 3 tablespoons white sugar
• 5 tablespoons melted butter

For the Cheesecake Filling:

• 3 tubs (8 ounces each) smooth cream cheese, softened
• 3/4 cup white sugar
• 3/4 cup sour cream
• 2 teaspoons vanilla extract

Instructions

Preparing the Pineapple Topping:

1. Preheat Oven: Preheat your oven to 350°F (175°C).
2. Caramelize Pineapple: In a small saucepan, melt 5 tablespoons of butter over medium heat. Stir in 2 tablespoons of brown sugar until dissolved.
3. Arrange Pineapple and Cherries: Pour the caramel mixture into a 9-inch springform pan. Arrange the pineapple slices in a single layer on top of the caramel. Place a chopped maraschino cherry in the center of each pineapple ring. Set aside.

Making the Graham Cracker Crust:

1. Combine Ingredients: In a medium bowl, combine 1 cup of graham cracker crumbs and 3 tablespoons of white sugar. Stir in 5 tablespoons of melted butter until the mixture resembles wet sand.
2. Press Crust: Press the graham cracker mixture evenly over the pineapple slices, ensuring the crust is firmly packed.
3. Bake Crust: Bake the crust for 10 minutes, then remove from the oven and let cool.

Preparing the Cheesecake Filling:

1. Beat Cream Cheese: In a large bowl, beat the softened cream cheese with an electric mixer until smooth and creamy.
2. Add Sugar: Gradually add 3/4 cup of white sugar, beating until well combined.
3. Incorporate Sour Cream and Vanilla: Mix in 3/4 cup of sour cream and 2 teaspoons of vanilla extract until the mixture is smooth.
4. Pour Filling: Pour the cheesecake filling over the cooled graham cracker crust, spreading it evenly.

Baking the Cheesecake:

1. Bake Cheesecake: Place the springform pan in a larger baking pan. Pour hot water into the larger pan to reach halfway up the sides of the springform pan, creating a water bath. This helps prevent cracks in the cheesecake.
2. Bake in Water Bath: Bake at 350°F (175°C) for 50-60 minutes, or until the center is set but still slightly jiggly.
3. Cool: Turn off the oven and let the cheesecake cool in the oven with the door slightly open for about 1 hour. This gradual cooling helps prevent cracks.
4. Refrigerate: Remove the cheesecake from the oven and water bath. Refrigerate for at least 4 hours, or overnight, to set completely.

Serving the Cheesecake:

1. Invert the Cheesecake: Run a knife around the edge of the springform pan to loosen the cheesecake. Carefully invert the cheesecake onto a serving plate so that the pineapple topping is on top.
2. Slice and Serve: Slice the cheesecake into wedges and serve chilled. Enjoy!

Cook’s Notes

• Room Temperature Ingredients: Ensure the cream cheese, sour cream, and eggs are at room temperature before starting. This helps create a smooth, lump-free cheesecake filling.
• Water Bath Tips: To prevent water from leaking into the springform pan, wrap the outside of the pan with aluminum foil before placing it in the water bath.
• Preventing Cracks: Avoid overmixing the cheesecake batter to prevent incorporating too much air, which can cause cracks during baking.

Variations

• Tropical Twist: Add a tablespoon of rum extract or coconut extract to the cheesecake filling for a tropical flavor.
• Nutty Crust: Replace the graham cracker crumbs with crushed nuts such as pecans or almonds for added texture and flavor.
• Mini Cheesecakes: Use a muffin tin to create individual servings. Adjust the baking time to 20-25 minutes.

Keto and Low-Carb Version

For the Pineapple Topping:

• Use a low-carb sweetener like erythritol instead of brown sugar.
• Use fresh pineapple slices and cherries in moderation, as they contain natural sugars.

For the Graham Cracker Crust:

• Replace graham cracker crumbs with a mix of almond flour and coconut flour. Use a low-carb sweetener instead of white sugar.

For the Cheesecake Filling:

• Use a low-carb sweetener instead of white sugar.
• Ensure all other ingredients are low-carb and keto-friendly.

Frequently Asked Questions (FAQs)

1. Can I make this cheesecake ahead of time?
   • Yes, you can make Pineapple Upside-Down Cheesecake a day in advance. It actually tastes better after chilling overnight.
2. How do I store leftovers?
   • Store leftovers in an airtight container in the refrigerator for up to 5 days.
3. Can I freeze this cheesecake?
   • Yes, you can freeze this cheesecake. Wrap it tightly in plastic wrap and aluminum foil, then freeze for up to 2 months. Thaw in the refrigerator overnight before serving.
4. What if I don’t have a springform pan?
   • You can use a regular 9-inch cake pan, but be extra careful when inverting the cheesecake to avoid breaking the crust.
5. Can I use canned pineapple chunks instead of slices?
   • Yes, you can use pineapple chunks, but the presentation will be different. Make sure to drain them well to avoid excess moisture.

Pineapple Upside-Down Cheesecake is a delightful dessert that combines the best of both worlds: the caramelized fruitiness of a pineapple upside-down cake and the rich, creamy texture of a cheesecake. With its stunning presentation and irresistible taste, it’s sure to become a favorite in your dessert repertoire. Enjoy making and savoring this delightful treat, and don’t forget to share it with loved ones. Happy baking!