Classic Pineapple Upside-Down Cake

If you’re looking for a dessert that conjures wonderful memories of days gone by, as well as being incredibly delicious. You’ve come to the right place.

This cake is a wonderful yellow butter cake topped with an amazing caramel sauce, pineapples and cherries. It’s as beautiful in presentation as it is in incredible taste.

A pineapple upside-down cake on a white platter next to a glass of orange and a cup of coffee.

HOW TO MAKE A CLASSIC PINEAPPLE UPSIDE-DOWN CAKE

This cake is truly not difficult to eat. We start by making a simple caramel sauce for the bottom of the pan (which will eventually be the top of the cake)!

Add the pineapple slices, cherries, and then the batter…and bake to perfection!

Watch us show you how to make this classic cake! It’s easy and so much fun!

CANNED OR FRESH PINEAPPLES

You know us, we always encourage you to use the freshest ingredients, and by all means, using fresh pineapple is great.  But, we’ve tried it both ways, and fresh can be a bit problematic…there is a lot of water that is released that compromises the cake.

There are adjustments that can be made if you decide to cut up a fresh pineapple, but honestly, getting good quality, canned sliced pineapple, in pineapple juice, yields a wonderful cake, too. (Shhh..maybe even better!).

EXPERT TIP: This classic cake is often made in a 10-inch cast-iron skillet. It’s perfect for melting the butter and then pouring the batter and baking. We find once it’s time to invert the cooked cake, however, it is a little challenging. We’ve tested both cast-iron skillets and a 9-inch round (2-inch tall) cake pan, and they both have excellent results. Only difference? The cake pan version is MUCH easier to invert and release the cake. But if you want to keep it old school, go for it! You’ll probably just need an extra pair of hands to help when it’s time to flip the cake.

A hand placing a cherry in the whole of a pineapple ring in a cake pan.

PINEAPPLE UPSIDE-DOWN CAKE IS DELICIOUS AND IS BEAUTIFUL IN PRESENTATION

The batter for this produces a perfectly moist and flavorful cake for this amazing dessert.

As mentioned, this is a classic yellow butter cake.  Which happens to be the perfect match for the gooey caramel and juicy pineapples.

EXPERT TIP: The batter for this cake is somewhat thick. Use a rubber spatula to help gently spread the batter over the pineapples. As the cake bakes, you may see some of the butter bubbling along the edges of the pan. This is okay and is good. It forms an unbelievably delicious, almost candy-like exterior to the edge of the cake that is sublime.

Yellow butter cake batter being poured into a cake pan with pineapples and cherries.

After 45 minutes of baking, the cake will have risen slightly and turned a golden brown.

You may seem a thin layer of butter shimmering on the surface of the cake, this is normal.

EXPERT TIP: Insert a toothpick into the cake once you have reached 45 minutes. If the toothpick comes out clean, with no wet batter stuck to it, the cake is ready. If there is wet better attached to the toothpick, then the cake needs to go back in for another 5 to 10 minutes.

A toothpick inserted and then removed from a baked pineapple-upside down cake.

PINEAPPLE UPSIDE-DOWN CAKE IS A CLASSIC AMERICAN DESSERT

The pineapple upside-down cake was extremely popular back in the 50s and 60s and has seen a major comeback in recent years.

But actually, the cake dates all the way back to the 1800s and the pineapple upside-down cake is just one of numerous classic American cakes that made their place in so many homes across the country. Learn about more about American Cakes Throughout History from PBS.

And lifting the pan away from the inverted cake will make you feel like a rock star in your own kitchen.

Two hands pulling an inverted cake pan away from a pineapple upside-down cake.

If you’re interested in making another incredible American classic dessert, go with one of our favorites: Carrot Cake.

But in the meantime, if you’re looking to impress with a truly delicious and gorgeous cake, you just gotta try this recipe. Serve by the slice and just watch them go!

EXPERT TIP: Though this cake is wonderful at room temperature, there is something extra special when served still warm from baking. Comfort dessert food at its best.

A slice of pineapple upside-down cake on a white plate next to a mug of coffee.

THIS CAKE IS NOT DIFFICULT TO PREPARE

You will be surprised at how easy it is to make this incredible Classic Pineapple Upside Down Cake from scratch.

Of course, you could go with a box variety…but why no go a little extra distance and make it completely homemade?

You and your loved ones will enjoy this so much, it will probably become part of your regular dessert recipe rotation. It’s that good!

A close up view of a pineapple upside-down cake on a white platter.

Ready to impress with one of the best cakes of all time? Go for it!

And when you do, be sure to take a picture, post if on Instagram, and tag @howtofeedaloon and hashtag #howtofeedaloon!

A pineapple upside-down cake on a white platter next to a glass of orange and a cup of coffee.

Classic Pineapple Upside-Down Cake

This Classic Pineapple Upside-Down Cake was extremely popular in the 1950s and 1960 and has made a huge resurgence in the past few years.  And no wonder, it's so delicious!  You can use a 9 or 10-inch cast iron skillet, or a cake pan with 2-inch sides.  This cake is as beautiful in presentation as it is in taste!
5 from 7 votes
Print Pin Rate
Course: Dessert
Cuisine: American
Keyword: Classic dessert recipe, Dessert, Pineapple Upside-Down Cake
Prep Time: 20 minutes
Cook Time: 50 minutes
Total Time: 1 hour 10 minutes
Servings: 8 people
Calories: 567kcal

Equipment

  • 9-inch cake pan with 2-inch side, or 9 or 10-inch cast-iron skillet

Ingredients

FOR THE PINEAPPLE TOPPING

  • 6 tbsp unsalted butter melted
  • cup light brown sugar
  • 8 pineapple rings canned, or fresh
  • Maraschino cherries

FOR THE CAKE

  • cups all-purpose flour sifted
  • tsp baking powder
  • ¼ tsp Kosher salt
  • ¾ cup unsalted butter 1½ sticks, softened
  • 1 cup sugar
  • 2 large eggs
  • ¼ cup pineapple juice
  • 1 tbsp vanilla extract
  • ½ cup whole milk

Instructions

MAKE THE TOPPING

  • Pour the melted butter into cake pan or skillet.  
  • Sprinkle the brown sugar over the melted butter and then top with the pineapple slices, then place cherries in the centers of the rings and in the open spaces.

MAKE THE CAKE

  • Preheat the oven to 350°F.
  • In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
  • Using a stand mixer, or a hand mixer with a large bowl, cream the sugar with the butter, by mixing on medium until slightly fluffy and pale in color, about 3 to 40 minutes. Scraping down the sides of the bowl a couple of times.
  • Whisk in the eggs, pineapple juice, and vanilla extract.
  • With the mixer running, add half of the flour mixture, once incorporated, add half of the milk. Once incorporated repeat with remaining flour and then milk. Mix until fully combined. The batter will be somewhat thick.
  • Use a spatula to help pour the batter into the prepared pan and gently spread over the pineapples and cherries.
  • Bake for 45 minutes, or until a toothpick comes out clean when stuck into the center of the cake.
  • Let rest for 10 minutes, and then invert the cake on top of a cake stand or serving plate. 
  • Slice and serve warm or at room temperature.  Great with ice cream or whipped cream!

Video

Notes

If using fresh pineapple, you'll need to purchase extra pineapple juice.  Most canned pineapple slices are filled with 100% pineapple juice. 
A cast-iron skillet is traditional, but we find a 9-inch cake pan with 2-inch sides works just as well, and is much easier to invert and release the cake onto a platter.
The batter is fairly thick and will require a spatula or the back of a large spoon to help the batter out of the mixing bowl and to spread evenly over the pineapples and cherries.
Maraschino cherries can be found in the canned fruit section of your grocery store, or in the adult beverage condiment section. 
Insert a toothpick into the cake when the baking time is finished.  If no batter sticks to the toothpick when removed from the cake, it's ready.  If there is wet batter (not cake crumbs), then bake for another 5 to 10 minutes, and re-try the toothpick check.  Once no wet batter is stuck to the toothpick, the cake is ready.
We find the cake is best served warm, soon after baking.  But can also easily be briefly reheated in the microwave when serving the next day.  It's also delicious at room temperature. 

Nutrition

Serving: 1slice | Calories: 567kcal | Carbohydrates: 75g | Protein: 6g | Fat: 21g | Saturated Fat: 12g | Cholesterol: 123mg | Sodium: 110mg | Potassium: 254mg | Fiber: 1g | Sugar: 53g | Vitamin A: 924IU | Vitamin C: 6mg | Calcium: 94mg | Iron: 2mg
Tried this recipe? Take a Picture!Mention @HowToFeedALoon or tag #HowToFeedALoon!

POST UPDATE: This recipe was originally published in June 2018, but was updated with improved tweaks to the recipe, with new tips, photography, and a fabulous new video in February 2020!

13 Comments

  • Oh. My. Gosh! How inviting this pineapple cake looks! If I could give it more than 5 stars I would! I’m definitely saving the recipe for later.
    Thank you so much for sharing this fab idea and all of your precious tips and tricks. Such treasure. I’ll definitely be back for more of your recipes. Your blog is beneficial <3

    Best wishes,
    Ann

    • Hi Ann! Please forgive the delayed response! Thank you so much! We do love this pineapple upside-down cake so much! Been a family favorite for years! You blog is beautiful, by the way! We love it! Thanks so much!!! Kris & Wesley

  • Well it’s in the oven! My friend as been asking me for a while to make her one, so we both have to work midnights tonight, Christmas Eve so I am making to bring to her tonight. Very easy recipe can’t wait to try it.

    • Hi Janice!! So sorry for the very delayed response!!! So glad you made this cake (one of our all-time favs), and we are really excited to hear how it turned out!! Hope you had a wonderful Christmas and Happy New Year!! All the best, Kris & Wesley

  • Hi Kris! I haven’t seen Pineapple upside-down Cake since I was a child. I loved it! I’m going to a BBQ this Saturday with some (don’t tell anyone I said so) pretty stuck-up friends, and I’m going to bring this along. I bet that my friends will turn up their noses at the fancy catered desserts and gobble this down! LOVE< LOVE< LOVE this post! Thank you!

    • We LOVE everything about this, Heather!!! You will be the hit of the BBQ, we have no doubt! Please let us know how it turns out and what those ‘stuck-up’ friends think about your beautiful cake!! Love it! xoxo Kris & Wesley

    • Update on the BBQ: They loved it! I’m thinking in hind site that I probably should have made 2 cakes as some were looking for seconds. I left with a list of email addresses of those who requested that I forward your recipe. You’re a star! Thanks again for posting this; it really was a treat to be able to share it with these people.

      • That is such amazing news! Sounds like you were the star of the BBQ! Way to go!! So glad folks loved it. and thank you so much or letting us know, we really do appreciate it. Keep your eyes peeled for more recipes and let us of any others you have success with. xoxo Kris & Wesley

Leave a Reply

Your email address will not be published. Required fields are marked *