Description
Listen, somebody looked at a classic pineapple upside-down cake and a creamy cheesecake and said “why choose?” and honestly, that person deserves a medal. This is what happens when two iconic desserts have a love child and that child is PERFECT. You’ve got the caramelized pineapple rings with their glossy, buttery glaze situation happening on top, sitting on the creamiest, tangiest cheesecake layer you’ve ever tasted, all held up by a buttery graham cracker crust. It’s retro. It’s tropical. It’s fancy but also grandma’s-house-in-the-best-way. I made this for a summer potluck and three different people asked if I was secretly a professional baker. I’m not, but this dessert makes you LOOK like one. Someone’s aunt took a bite, closed her eyes, and said “this tastes like vacation.” Another guy had two slices and said he was “emotionally compromised.” These are the reactions you want from dessert.
Ingredients
For the Pineapple Topping:
- 3 tbsp unsalted butter
- 1/2 cup brown sugar, packed (dark or light, your call)
- 1 can (20 oz) pineapple rings, drained and VERY well dried (save about 7–9 rings)
- 7–9 maraschino cherries, drained and dried (the classic red ones for that retro look)
- Optional: 1/4 cup chopped pecans or walnuts if you want some crunch
For the Crust:
- 2 cups graham cracker crumbs (about 16–18 crackers, crushed)
- 1/3 cup granulated sugar
- 6 tbsp unsalted butter, melted
- Pinch of salt
For the Cheesecake:
- 24 oz (three 8-oz blocks) cream cheese, softened to room temp (this is crucial)
- 1 cup granulated sugar
- 3 large eggs, room temperature
- 1 cup sour cream (full-fat, don’t be scared)
- 1/4 cup pineapple juice (from the can you drained)
- 1 tbsp vanilla extract
- 1 tbsp all-purpose flour
- 1/4 tsp salt
Instructions
Grab a 9-inch springform pan. This is non-negotiable—you need that removable bottom.
Wrap the OUTSIDE of the pan (bottom and sides) tightly with heavy-duty aluminum foil. Like, really wrap it. Multiple layers. This prevents water from the water bath getting in.
Have a roasting pan ready that’s large enough to hold your springform pan. We’re doing a water bath situation.
Preheat your oven to 325°F (163°C).
In a small saucepan over medium heat, melt 3 tablespoons of butter. Add the brown sugar and stir until it’s all melty and combined, about 2 minutes. It should look like caramel sauce.
Pour this gorgeous caramel into the bottom of your prepared springform pan. Spread it evenly.
Pat those pineapple rings VERY dry with paper towels. Like, obsessively dry. Arrange them in a single layer over the caramel—you should fit about 7-9 rings depending on how you arrange them. Overlap slightly if needed.
Place a cherry in the center of each pineapple ring (classic move). If you’re using nuts, sprinkle them in the gaps.
Set this aside. Admire how pretty it already looks.
In a medium bowl, mix graham cracker crumbs, 1/3 cup sugar, melted butter, and a pinch of salt until it looks like wet sand.
Press this mixture FIRMLY over the pineapple layer. Use the bottom of a measuring cup to really pack it down. You want it compact.
Get into the edges too. A firm, even crust is key.
In a large bowl (or stand mixer), beat the softened cream cheese on medium speed for 3-4 minutes until it’s completely smooth and fluffy. Scrape down the sides at least twice. Any lumps now = lumps forever.
Add 1 cup sugar and beat for another 2 minutes until light and creamy.
Add eggs ONE AT A TIME, beating on low speed after each addition. Don’t rush this. Each egg should be fully incorporated before adding the next.
Add sour cream, pineapple juice, vanilla, flour, and salt. Mix on low just until combined and smooth. Don’t overmix at this stage.
The batter should be silky, thick, and pourable.
Pour the cheesecake batter over the crust in the springform pan. Smooth the top with a spatula.
Tap the pan gently on the counter a few times to release any air bubbles.
Place the springform pan in your roasting pan. Put them both in the oven.
Carefully pour hot water into the roasting pan until it comes about halfway up the sides of the springform pan. This water bath keeps the cheesecake from cracking.
Bake at 325°F for 60-75 minutes. The cheesecake is done when the edges are set but the center still has a slight wobble (about 3 inches in diameter). It should jiggle like Jell-O, not liquid.
Turn off the oven, crack the door open slightly, and let the cheesecake sit in there for 1 hour. This gradual cooling helps prevent cracks.
After an hour, remove from the oven and water bath. Let it cool on the counter for another hour.
Once cooled to room temperature, cover the pan with plastic wrap (don’t let it touch the surface) and refrigerate for at least 8 hours, preferably overnight.
This chill time is MANDATORY. The cheesecake needs to set completely.
When you’re ready to serve, run a thin knife around the edge of the pan to loosen.
Place a serving plate upside down on top of the springform pan.
Hold them together firmly and flip the whole thing over quickly and confidently. Don’t hesitate—commit to the flip.
Remove the springform pan sides and bottom carefully.
If any pineapple rings stick to the pan, just place them back where they belong. If any caramel is left in the pan, heat it slightly and drizzle it over the top.
Behold your masterpiece.
Notes
This is gorgeous enough to serve on its own, but here are some ideas:
- Dollop of fresh whipped cream on each slice
- Drizzle of extra caramel sauce for the truly decadent
- A sprinkle of toasted coconut for extra tropical vibes
- Serve with vanilla ice cream for full dessert overload
- Garnish with fresh mint leaves for a pop of color
- Pair with coffee or tropical drinks like piña coladas
- Prep Time: 30 minutes
- Cook Time: 70 minutes
Nutrition
- Calories: ~380 kcal
- Fat: ~22g
- Carbohydrates: ~38g
- Protein: ~7g