Delicious Pineapple Upside-Down Cheesecake with a caramelized topping

Pineapple Upside-Down Cheesecake Cake

There’s something truly magical about a Pineapple Upside-Down Cheesecake Cake—it instantly brings sunshine and smiles to the table. This dessert combines a creamy cheesecake base with a luscious pineapple topping, delivering both warmth and sweet nostalgia from the very first bite.

Did you know the original upside-down cake dates back to the early 1920s? This creative recipe takes the timeless charm of a pineapple upside-down cake and elevates it with the rich decadence of cheesecake. The result? A show-stopping treat perfect for any occasion!

Whether you’re celebrating a birthday, hosting a potluck, or simply indulging your sweet tooth, this cake is bound to impress. It’s simple enough for a weeknight bake, yet elegant enough for guests. If you enjoy classics like our Southern Cornmeal Hoecakes, you’ll absolutely adore this unique creation. Ready to make sweet memories? Let’s dive in!

What Is Pineapple Upside-Down Cheesecake Cake?

The name says it all! This dessert is a perfect marriage of two beloved classics: the smooth creaminess of cheesecake and the caramelized sweetness of pineapple rings. Baked “upside-down,” it reveals a gorgeous topping once flipped, making every slice a feast for the eyes as well as the taste buds.

As the saying goes, “The way to the heart is through the stomach.” One bite of this cake will win over everyone at the table. So grab your spatula—it’s time to flip dessert on its head!

Why You’ll Love This Pineapple Upside-Down Cheesecake Cake

This cake is a true flavor celebration:

  1. Creamy & Dreamy: The silky cheesecake layer adds a rich depth that pairs perfectly with sweet, tangy pineapple.

  2. Budget-Friendly Indulgence: Skip the pricey bakery—this recipe delivers gourmet flavor at home for a fraction of the cost.

  3. A Picture-Perfect Topping: Golden pineapple rings and bright maraschino cherries create a vibrant, irresistible finish.

If you love traditional favorites like our Chocolate Lava Cake, this dessert will quickly become a new favorite.

How to Make Pineapple Upside-Down Cheesecake Cake

Quick Overview

You might be surprised by how easy this recipe is! With a buttery crust, creamy cheesecake filling, and caramelized pineapple topping, you’ll have a beautiful cake ready in about an hour.

Key Ingredients

  • 1 (20 oz) can sliced pineapple in heavy syrup

  • 1 cup brown sugar

  • 6 tbsp unsalted butter

  • 1 cup graham cracker crumbs

  • ½ cup sugar

  • 2 (8 oz) packages cream cheese, softened

  • 1 tsp vanilla extract

  • 3 large eggs

  • 1 tbsp all-purpose flour

  • Maraschino cherries (for garnish)

Delicious Pineapple Upside-Down Cheesecake with a caramelized topping

Step-by-Step Instructions

  1. Prepare the Topping: Drain pineapple slices and reserve the syrup. In a skillet, melt butter with brown sugar until bubbling. Arrange pineapple slices and cherries in the bottom of a greased springform pan. Pour the butter mixture over them.

  2. Make the Crust: Combine graham cracker crumbs with sugar. Stir in melted butter until crumbly, then press firmly over the pineapple layer.

  3. Prepare the Filling: Beat softened cream cheese with sugar until smooth. Add vanilla and flour, then mix in eggs one at a time until fully incorporated.

  4. Assemble & Bake: Pour cheesecake batter over the crust. Bake at 325°F (160°C) for 50–60 minutes, or until the center is just set.

  5. Cool & Flip: Let cool completely, then carefully invert onto a serving plate. Drizzle with reserved syrup if desired. Slice, serve, and enjoy!

Serving Suggestions

This cake shines on its own, but you can take it up a notch by pairing it with vanilla ice cream, whipped cream, or a fresh fruit salad. A glass of Southern-style sweet tea also makes the perfect companion.

Tips for Success

  • Room-Temperature Ingredients: Cream cheese and eggs blend best when not cold.

  • Avoid Overmixing: Gentle mixing prevents cracks in your cheesecake.

  • Fresh Twist: For extra zing, try using fresh pineapple instead of canned.

Storage & Freezing

  • Refrigerator: Store leftovers in an airtight container for up to 5 days.

  • Freezer: Wrap slices tightly in plastic wrap and foil, then freeze for up to 2 months. Thaw overnight in the fridge before serving.

To reheat, warm individual slices in the microwave for 15–20 seconds.


Now you’re ready to wow your family and friends with this Pineapple Upside-Down Cheesecake Cake. It’s a delicious twist on a classic that will be remembered long after the last bite!

Pineapple Upside-Down Cheesecake Cake

A delightful twist on the classic dessert featuring creamy cheesecake layered over caramelized pineapple and a buttery crust.
Prep Time 20 minutes
Cook Time 1 hour
Total Time 1 hour 20 minutes
Servings: 8 servings
Course: Dessert, Sweet Treat
Cuisine: American, Souther
Calories: 350

Ingredients
  

For the Topping
  • 1 can sliced pineapple in heavy syrup 20 oz can, drained
  • 1 cup brown sugar
  • 6 tbsp unsalted butter melted
  • Maraschino cherries to taste Maraschino cherries for garnish
For the Crust
  • 1 cup graham cracker crumbs
  • ½ cup sugar
For the Cheesecake Filling
  • 2 packages cream cheese 8 oz packages, softened
  • 1 tsp vanilla extract
  • 3 large eggs
  • 1 tbsp all-purpose flour

Method
 

Preparation
  1. Drain the pineapple slices and reserve the syrup. In a skillet, melt butter and brown sugar over medium heat until bubbling. Layer the pineapple slices and cherries in the bottom of a greased springform pan, pouring the butter mixture over them. Set aside.
  2. In a bowl, combine graham cracker crumbs and sugar. Add melted butter and mix until crumbly. Press this mixture firmly into the bottom over the pineapple layer.
  3. In a large bowl, blend softened cream cheese with sugar until smooth. Mix in the vanilla extract and flour. Add eggs one at a time, blending well after each addition.
  4. Pour the cheesecake filling over the graham cracker crust and smooth the top.
Baking
  1. Bake in a preheated oven at 325°F (160°C) for 50-60 minutes or until the center is set.
Cooling and Serving
  1. Allow the cake to cool completely before inverting onto a serving plate. Drizzle with remaining syrup if desired. Slice and enjoy!

Notes

Make sure cream cheese and eggs are at room temperature for a smoother batter. Avoid overmixing to prevent cracking. Try using fresh pineapple for added flavor.

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