
This cheesecake flips the script on pineapple upside-down cake by turning it into a smooth, creamy delight. It brings together sweet tropical flavors with rich cheesecake goodness for a dessert that feels both nostalgic and fresh at the same time.
I whipped up this treat when my sister couldn't pick between two favorites for her birthday - cheesecake or pineapple upside-down cake. The combo was such a success that my family now asks for it at practically every get-together.
Ingredients
- Graham cracker crumbs: give that wonderful crunch against the soft filling
- Brown sugar: brings a warm, molasses flavor to the base
- Cream cheese at room temperature: makes sure your filling turns out completely smooth
- Cornstarch: works to keep the top from splitting while it bakes
- Maraschino cherries: add bright spots of color and sweetness throughout
- Canned pineapple pieces: bring a taste of the tropics in every mouthful
- Heavy cream: makes the filling extra lush and velvety
Step-by-Step Instructions
- Prepare the Pan:
- Getting your pan ready is super important for a flawless cheesecake. Give it a good coat of non-stick spray, put down parchment paper, then spray again. This three-layer approach helps your cake come out clean after it chills.
- Create the Crust:
- Combine graham crumbs with both types of sugar, then slowly pour in melted butter until it looks like damp sand. Push firmly into your prepared pan, making sure it's level across the bottom and about an inch up the sides. Bake until it's lightly golden and smells amazing.
- Mix the Filling:
- Whip the cream cheese for a full 4-5 minutes until it's perfectly smooth, making sure to clean the sides of the bowl often. This long beating adds air for a lighter texture and gets rid of any lumps. Mix in other ingredients except eggs until just blended.
- Add Eggs and Fruit:
- Softly mix in the eggs to keep from adding too much air, which might cause cracks. Then carefully stir in cherries and pineapple bits, spreading them evenly through the mix. Pour into your cooled crust.
- Master the Water Bath:
- Set your cheesecake pan on a flat pan or inside a bigger pan with about an inch of hot water. This creates moisture that stops the top from cracking and helps everything cook evenly.
- Follow the Temperature Stages:
- Start baking at 300°F to firm up the edges, then drop to 225°F to slowly cook the middle. This two-step method makes the perfect creamy texture without overcooking.

The maraschino cherries are my special touch in this dish. My grandma always used them in her pineapple upside-down cake, and mixing them all through the cheesecake instead of just on top brings back sweet memories of baking with her in her small kitchen. The bright red spots against the light yellow filling look stunning when you cut a slice.
Storage Tips
This cheesecake stays fresh in the fridge for up to 5 days. Keep it in an airtight container or wrapped tightly with plastic to stop it from picking up other food smells. For the best flavor, add the whipped cream topping right before you serve it, not ahead of time.
Make It Your Own
Don't be afraid to try different fruits based on what you have. You can use fresh pineapple instead of canned, just make sure to dry it well first. For a grown-up twist, soak the pineapple in rum for an hour before adding it to the mix. You might also swap the graham cracker base for vanilla wafers or shortbread cookies.
Serving Suggestions
For a wow factor, put this cheesecake on a pretty cake stand with extra pineapple slices and cherries around the bottom. A spoonful of fresh whipped cream on each piece cuts through the sweetness just right. At a tropical brunch, serve with mimosas made using pineapple juice instead of orange for a fun twist.
Common Questions About This Recipe
- → Can I use fresh pineapple instead of canned?
Absolutely, fresh pineapple works great. Just make sure it's ripe and check if you need extra sugar since fresh fruit isn't always as sweet as canned.
- → What is the purpose of cornstarch in the cheesecake?
Cornstarch makes the cheesecake more stable, helps stop cracks from forming, and gives you that dreamy, silky texture everyone loves.
- → How do I prevent the cheesecake from cracking?
Go with a lower oven temp, don't leave it in too long, and let it cool down slowly to avoid those quick temperature changes that often lead to cracks.
- → Can I omit the cherries or substitute with another fruit?
You can definitely skip the cherries or try something different like chopped strawberries or mango chunks for your own special version.
- → How long does the cheesecake need to chill?
Let it rest in the fridge overnight or at least 6-8 hours so it can firm up properly and taste its best.
- → What's the best way to cut clean slices?
Grab a sharp knife, dip it in hot water before each slice, and wipe the blade clean between cuts for those picture-perfect portions.