Name: Pineapple Right Side Up Cheesecake
Prep time: 20 min
Cook time: PT-485893H51M36S
Total time: 5 h
Cuisine: American
Ingredients: 1 1/2 cups graham cracker crumbs; 1/4 cup sugar; 1/3 cup melted butter; 1/4 cup butter, melted (for topping); 1/2 cup packed brown sugar (for topping); Pineapple rings (canned or fresh); Maraschino cherries (optional, for center of rings); 3 (8 oz) blocks cream cheese, softened; 1 cup sugar; 1 tsp vanilla extract; 3 eggs; 1/2 cup sour cream; 1/2 cup crushed pineapple (well-drained)

This Pineapple Right Side Up Cheesecake is a luscious blend of creamy cheesecake, sweet pineapple, and a buttery graham cracker crust. The unique twist? The pineapple and brown sugar topping goes on the bottom of the pan before baking, so when flipped, it reveals a beautiful caramelized pineapple top—making it as stunning as it is delicious.

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Crust:

1 1/2 cups graham cracker crumbs

1/4 cup sugar

1/3 cup melted butter

Topping Layer:

1/4 cup butter, melted

1/2 cup packed brown sugar

Pineapple rings (canned or fresh)

Maraschino cherries (optional, for center of rings)

Cheesecake Filling:

3 (8 oz) blocks cream cheese, softened

1 cup sugar

1 tsp vanilla extract

3 eggs

1/2 cup sour cream

1/2 cup crushed pineapple (well-drained)

Directions

Preheat the oven to 325°F (163°C). Grease a 9-inch springform pan. If using a water bath, wrap the bottom of the pan in foil to prevent leaks.

Make the topping: Pour melted butter and brown sugar into the bottom of the pan. Arrange pineapple rings evenly on top. Place a maraschino cherry in the center of each ring if using.

Prepare the crust: Mix graham cracker crumbs, sugar, and melted butter. Press this mixture firmly over the pineapple layer in the pan. Chill the pan while preparing the filling.

For the filling: Beat the softened cream cheese and sugar until smooth and creamy. Add eggs one at a time, mixing well after each addition. Then add vanilla extract, sour cream, and crushed pineapple. Mix until just combined.

Pour the filling evenly over the chilled crust and pineapple layer.

Bake for 50–60 minutes, or until the center is just set but still slightly jiggly. Turn off the oven, crack the oven door, and let the cheesecake sit inside for 30 minutes to prevent cracking.

Remove the cheesecake from the oven and allow it to cool completely at room temperature. Then refrigerate for at least 4 hours or overnight.

To serve, run a knife around the edges of the pan, carefully remove the springform side, and invert the cheesecake onto a serving plate so the pineapple layer is now on top.

Servings and timing

This recipe serves about 10-12 people.

Prep time: 20 minutes

Bake time: 50-60 minutes

Cooling and chilling time: 4+ hours (preferably overnight)

Variations

For a tropical twist, add shredded coconut to the crust mixture.

Substitute the crushed pineapple in the filling with mango or peach for a different fruit flavor.

Use fresh pineapple rings for a more natural taste and texture.

For a dairy-free version, swap cream cheese and sour cream with plant-based alternatives.

Add a splash of rum or coconut extract to the filling for extra depth and island vibes.

Storage/reheating

I store this cheesecake covered tightly with plastic wrap or in an airtight container in the refrigerator for up to 4-5 days. Cheesecake doesn’t freeze well with the pineapple topping, as it can become watery when thawed. When ready to serve, I always let it sit at room temperature for about 15 minutes to soften slightly before slicing.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works wonderfully! Just be sure to slice the rings evenly and drain any excess juice well to avoid a soggy crust.

What if I don’t have a springform pan?

A springform pan is ideal because it makes it easier to invert the cheesecake without damaging it. If you don’t have one, you can use a regular cake pan, but be very careful when flipping the cheesecake and consider lining it with parchment paper for easier removal.

Can I make this cheesecake ahead of time?

Absolutely! I recommend making it a day ahead so it has plenty of time to chill and set, which improves the flavor and texture.

How do I prevent cracks on the cheesecake surface?

Baking at a low temperature, using a water bath, and letting the cheesecake cool gradually inside the oven with the door cracked helps prevent cracks. Also, avoid overmixing the batter once eggs are added.

Can I skip the cherries?

Yes, the cherries are optional and mainly for decoration. The pineapple rings alone make a beautiful and tasty topping.

Conclusion

Making this Pineapple Right Side Up Cheesecake is one of my favorite ways to impress guests and enjoy a tropical dessert that’s both creamy and visually stunning. The combination of caramelized pineapple topping and smooth cheesecake creates a perfect balance of flavors and textures. Whether for a special occasion or a weekend treat, this recipe is one I keep coming back to because it’s reliably delicious and elegant. I hope you enjoy making and sharing it as much as I do!

Recipe: