Tasty Pineapple Right Side Up

Category: Desserts That Transform Moments

Dive into the sunny flavors of this Pineapple Right Side Up Cheesecake, mixing tangy pineapple and cherries with a silky cream cheese base. The treat begins with a basic graham cracker bottom baked until golden, topped with a rich cheesecake mixture enhanced with vanilla notes and creamy sour cream. Mix in zesty cherries and juicy pineapple pieces for pops of island taste. Once baked until just set, finish with swirls of whipped cream, fresh pineapple cuts, and bright cherries. It's fancy yet doable, striking the perfect mix between exotic charm and homey richness!

Sarah Crisp
Recipe By Sarah Crisp Sarah Crisp
Last updated on Tue, 16 Sep 2025 18:39:59 GMT
A slice of pineapple upside down cake. Pin
A slice of pineapple upside down cake. | cookrisp.com

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.
A slice of pineapple upside down cake.
A slice of pineapple upside down cake. | cookrisp.com

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.

Pineapple Right Side Up Cheesecake

Smooth cheesecake topped with pineapple and cherries on a graham crust.

Prep Time
30 minutes
Time to Cook
107 minutes
Complete Time
137 minutes
Recipe By Sarah Crisp: Sarah Crisp

Recipe Type: Sweet Comfort

Level of Difficulty: Moderate Difficulty

Cuisine Style: American

Makes: 8 Number of Servings

Dietary Categories: Suitable for Vegetarians

Ingredients You’ll Need

→ Graham Cracker Crust

01 1 ¼ cups crushed graham crackers
02 46 grams light brown sugar
03 42 grams white sugar
04 6-7 tbsp melted butter (add gradually, you might not need it all)

→ Cheesecake

05 16 ounces softened cream cheese
06 80 grams sour cream at room temp
07 1 tablespoon heavy cream at room temp
08 1 tablespoon pure vanilla extract
09 140 grams white sugar
10 2 tablespoons cornstarch
11 2 eggs at room temp
12 25 halved maraschino cherries
13 4 canned pineapple rings, chopped into chunks

→ Garnish

14 Fresh whipped cream
15 Leftover canned pineapple slices, cut in half
16 Whole maraschino cherries with stems

How to Make It

Step 01

Heat your oven to 300°F (149°C). Give a 6x3-inch pan with removable bottom a good coat of non-stick spray, put down parchment, then spray again. Combine all your crust stuff and push firmly into the pan bottom. Pop in the oven for 10-12 minutes. Let it cool on a rack sitting over a baking sheet.

Step 02

Whip the cream cheese until it's super smooth, about 4-5 minutes, making sure to scrape the bowl down several times. Stir in your sour cream, heavy cream, vanilla, white sugar, and cornstarch until everything's well mixed. Gently add the eggs, then carefully fold in your halved cherries and pineapple chunks.

Step 03

Pour your mixture into the cooled crust. Bake at 300°F (149°C) for 12 minutes, then drop the temperature to 225°F (107°C) and keep baking for another 95 minutes without peeking. When done, turn the oven off but leave the cake inside for an hour, then prop the door open slightly for one more hour.

Step 04

Let the cheesecake cool completely on a rack, then stick it in the fridge overnight. Take it out of the pan, put it on a nice cake plate, and top with swirls of whipped cream, pineapple pieces, and stemmed cherries.

Things You'll Need

  • 6x3-inch pan with removable bottom
  • Baking sheet
  • Large mixing bowl
  • Electric mixer (hand or stand)
  • Flexible spatula
  • Fridge
  • Serving plate
  • Baking parchment

Allergen Information

Always read labels for allergens and consult your doctor if unsure.
  • Has dairy products (cream cheese, sour cream, heavy cream)
  • Contains wheat from graham crackers
  • Has eggs

Nutritional Breakdown (Per Serving)

This is for general info and isn't a replacement for professional advice.
  • Calories: 500
  • Fat Content: ~
  • Carbohydrates: ~
  • Protein Content: ~