Pineapple Upside-Down Cheesecake

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Description
This stunning dessert combines two all-time favorites: classic pineapple upside-down cake and rich New York-style cheesecake. Sweet caramelized pineapples and cherries crown a moist cake base, while a velvety cheesecake layer sits above it all. It’s buttery, fruity, and luxuriously creamy — the ultimate showstopper.

Origin
Pineapple upside-down cake became popular in the U.S. in the 1920s thanks to canned pineapple. Cheesecake, especially the New York-style, has roots in early 20th-century America. This hybrid dessert has gained traction in bakeries and online communities as a modern fusion.

Ingredients with Quantities

For the Pineapple Topping:

  • ¼ cup unsalted butter, melted
  • ½ cup brown sugar
  • 6–7 canned pineapple rings (drained)
  • 6–7 maraschino cherries

For the Cake Layer:

  • ½ cup unsalted butter, softened
  • ¾ cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1 ¼ cups all-purpose flour
  • 1 ½ tsp baking powder
  • ¼ tsp salt
  • ½ cup whole milk

For the Cheesecake Layer:

  • 3 (8 oz) packages cream cheese, softened
  • 1 cup granulated sugar
  • 3 large eggs
  • ½ cup sour cream
  • 1 tsp vanilla extract

Optional Ingredients

  • ½ tsp coconut extract (for tropical twist)
  • Zest of 1 lime (for brightness in cheesecake)
  • ¼ cup crushed pineapple (folded into cheesecake)
  • Toasted coconut flakes (for garnish)

Instructions

  1. Prep your pan: Grease a 9-inch springform pan. Wrap the outside with foil if using a water bath.
  2. Make pineapple topping: Pour melted butter into the bottom of the pan and sprinkle brown sugar evenly over it. Arrange pineapple rings over the sugar. Place a cherry in the center of each ring.
  3. Make the cake batter: Cream together butter and sugar until fluffy. Add eggs one at a time, then vanilla. In a separate bowl, whisk flour, baking powder, and salt. Alternate adding dry ingredients and milk to the batter. Mix until smooth.
  4. Spread cake layer: Gently spoon and spread the cake batter over the pineapple layer, being careful not to disturb the design.
  5. Bake cake layer: Bake at 350°F (175°C) for 25–30 minutes, until lightly golden and just set. Remove from oven and let cool for 10 minutes.
  6. Make cheesecake filling: In a large bowl, beat cream cheese until smooth. Add sugar and beat again. Mix in eggs one at a time. Add sour cream and vanilla, mix until creamy.
  7. Add cheesecake layer: Pour cheesecake batter gently over the baked (and cooled) cake layer. Smooth the top.
  8. Bake cheesecake: Reduce oven temp to 325°F (160°C). Bake for 50–60 minutes or until the center is just set. Let it cool in the oven with the door cracked for 1 hour.
  9. Chill: Refrigerate the cheesecake for at least 6 hours or overnight before serving.
  10. Flip to reveal: Once fully chilled, carefully invert the cheesecake onto a serving plate to reveal the pineapple topping on top.

Tips for Success
Pat pineapples dry before layering to avoid sogginess. Use room temperature cream cheese for smooth filling. Let the cake layer cool before adding cheesecake to prevent sinking. Chill overnight for the best texture and easiest flipping.

Recommendations
Serve with whipped cream, a drizzle of caramel sauce, or toasted coconut. Pair with a tropical cocktail like a piña colada or a vanilla latte. Want mini versions? Try baking them in jumbo muffin tins!

Nutrition per slice (based on 12 servings, approximate)
Calories: 510
Fat: 32g
Saturated Fat: 19g
Carbohydrates: 47g
Sugar: 33g
Protein: 7g
Fiber: 1g
Sodium: 290mg

Want a shortcut version with boxed cake mix or crushed pineapple? I can give you that too — just say the word!

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