Who Invented the Pineapple Upside Down Cake
The pineapple upside-down cake, as we know it today, doesn’t have a single inventor but rather evolved from a long tradition of skillet cakes made with fruit and sugar.
The concept of “upside-down” cakes predates the pineapple version and goes back centuries—early American cooks made them with apples, cherries, or other seasonal fruits in cast iron skillets.
The modern pineapple upside-down cake likely gained popularity in the early 20th century, around the 1920s, when canned pineapple became widely available. The key player in its rise was the Dole Pineapple Company (then called Hawaiian Pineapple Company).
In 1925, Dole sponsored a recipe contest to promote its canned pineapple, receiving over 2,500 recipes for pineapple upside-down cake alone. This propelled the cake into the American mainstream.
While no single person can be credited with inventing it, the Dole company played a major role in popularizing the version featuring canned pineapple rings, maraschino cherries, and a brown sugar topping. The cake has remained a classic ever since.
Pineapple Upside Down Cake Recipe
Equipment
- 1 Cast Iron Pan
Ingredients
- ⅔ cup butter
- ¾ cup brown sugar
- 1 can pineapple slices
- maraschino cherries
- 1 box yellow cake mix
To Make Yellow Cake from Scratch
- 6.5 ounces sifted cake flour
- 1½ teaspoons baking powder
- ½ teaspoon salt
- 4 ounces butter at cool room temperature
- 1 cup sugar
- 2 large eggs
- 1 teaspoon vanilla
- ½ cup milk for pineapple upside down cake substitute pineapple juice for the milk
Instructions
- I used a large cast iron pan because it is heavy and I can stick it into the oven without having to worry about it burning the bottom of the cake. You can prepare the topping in a sauce pan and transfer it to a cake pan with 2 inch high sides but then you have two pans to clean up.
- Preheat your oven to 350° F degrees.
- Heat your pan over medium heat, add the butter and brown sugar to it and let the brown sugar melt and the mixture start to boil. My daughter asked me how to measure out ⅔ cup of butter and I told her she can let it come to room temperature and use a measuring cup or look at the butter wrapper for the conveniently marked measurements. She opted for the second idea.
- When the butter and brown sugar start boiling, remove from heat and start adding whole pineapple slices to the bottom of the pan. Cut some remaining slices in half and line the edge of the cast iron pan with the half pieces. Add some cherries to the holes in the whole pineapple slices and you are ready for the yellow cake batter.
- Prepare the box of yellow cake mix following the directions on the box. The recipe my daughter followed called for three eggs and for some reason she only added two but the end result was fine. I'm not sure how the third egg would have changed the taste, but her version was delicious.
- When the cake batter is ready, pour the cake mix into the cast iron pan and bake for the amount of time suggested on the cake box. You know it's done when you can stick a toothpick into the cake and it comes out clean. My daughter's cake took a little longer than the recipe said it would which is why the toothpick test is a better indicator.
- When the cake is done, remove it from the oven and immediately loosen the side of the cake from the pan with a dinner knife and let it cool for a few minutes. Once cooled down some, place a plate on top of the pan and flip it over. It should come out easily looking delicious and ready to eat.
- Whip up some homemade whip cream, add some birthday candles and you are ready to blow.
To Make Yellow Cake from Scratch
- This cake is made using The Creaming Method, where fats are mixed with sugar to form a mixture that is either smooth and creamy (cookie dough) or light and fluffy (cakes).
- Whisk the flour, baking powder and salt together really well. Set aside.
- Whisk the vanilla and milk together and set aside.
- In the bowl of a stand mixer fitted with the paddle attachment, cream the butter on medium speed. Add the sugar, and continue to cream until light and fluffy. Scrape the bowl as necessary.
- Add each egg, one at a time, mixing on low to begin with and then increasing the speed to medium or medium-high. Scrape the bowl between additions.
- With the mixer on the lowest speed, add half of the flour mixture. Beat until just incorporated.
- Add half the milk mixture, and mix in on low speed. Scrape the bowl and mix for a few more seconds.
- Add half of the remaining flour mixture, followed by the rest of the milk. Finish by adding the rest of the flour, and beat until just incorporated.
- Spoon the batter evenly over the pineapple layer and smooth gently.
- Follow the directions for baking pineapple upside down cake, above.
Cooking Tips
| Tip | Description | Why It Matters |
|---|---|---|
| Use a cast iron skillet | Prepare and bake the cake in the same skillet. | It distributes heat evenly and helps caramelize the topping. |
| Grease the pan well | Coat the skillet or pan with butter or cooking spray before adding sugar and fruit. | Prevents sticking and helps the cake release cleanly when flipped. |
| Arrange pineapple and cherries carefully | Place pineapple slices and cherries in a neat, even layer before adding batter. | Creates a visually appealing presentation once flipped. |
| Don't overmix the batter | Mix until just combined, whether using a mix or homemade batter. | Overmixing can make the cake tough or dry. |
| Let it cool slightly before flipping | Wait 5–10 minutes after baking before inverting the cake onto a plate. | Allows the caramel to settle and reduces the risk of burning yourself. |
| Use real butter and brown sugar | Melt them together in the skillet or pan before adding fruit. | Enhances flavor and creates a rich, gooey topping. |
| Serve with whipped cream | Top slices with freshly whipped cream or vanilla ice cream. | Adds creaminess and balances the cake’s sweetness. |
Memories
When I was a kid, my mom let me choose the cake she’d make for my birthday. For some reason—I’m still not exactly sure why—I always picked pineapple upside-down cake.
Maybe I loved the sweet pineapple with the yellow cake mix. Or maybe it was the only cake my mom ever made. Either way, it stuck.
Yesterday was my birthday, and my 11-year-old daughter asked what kind of cake I wanted. The moment she asked, I flashed back to my childhood, and just like I did at her age, I said pineapple upside-down cake. And you know what? She made it. Almost entirely on her own.
I only stepped in to help with the hot parts—getting the cast iron skillet in and out of the oven, then flipping it onto a plate. She did the rest herself, with some help from her good friend Duncan. That’s right—Duncan Hines Moist Classic Yellow Cake.
I was blown away.
Sure, you can make the batter from scratch (and I’ll share that recipe too), but when you’re in a rush—or you’re a kid trying this for the first time—a box mix works just fine. It skips a few steps and still delivers great flavor.
When my mom made this cake, she used a rectangular pan and crushed pineapple. This time, my daughter used a big cast-iron skillet and pineapple rings. My mom always topped hers with real whipped cream, so I showed my daughter how to make that from scratch, too.
And while my daughter made most of the cake herself, I stayed close, keeping an eye on things, especially around the hot stove and oven. Safety first, always.
10 Responses
once i have my stove this will be the first cake am going to bake,i love pineapples and the cake makes my mouth watery and it looks yummy!
I was planning on making something today, just not sure what! at midnite last nite hubby asked me if I could make a cake with pineapple slices…lol. So, this morning that is jsut what I did. It is awesome! I used a french vanilla mix tho(too warm to start from scratch today) and I decided to use a bundt pan just to be different. I cut the pineapple rings in half and molded them around the pan the tucked in cherries then the sauce and then cake! It is deeeee lish!!!
Hi Kelly, glad it all worked out for you. It really is a simple recipe and “deeee lish”!
going to make this p.m. first time for me. I love these cakes!
Great, let us know how it turns out for you. RG
I am really excited I just made this with a french Vanilla cake mix I have been craving it for some while it sure smells good! Thanks for the quick recipe.
You are welcome cherie – RG
did you know that there is now a cake mix for pineapple cake – duncan hines makes it! makes for a really great pineapple upside down cake. For added moistness and flavor, drain the pineapple and save the juice, add enough water to make the amount of water the cake mix call for and use this for the liquid. For years I have made the cakes with pineapple rings, but one time, i didn’t have anything but crushed pineapple, so that is what i used – the family loves it that way, you get pineapple in every bite of the cake! That’s the only way i make it now!
Hi Stephanie, sounds good and thanks for sharing this information with us. – RG
i ate one of those before! my family loves them.i was going to make one right now for an occassion,but i forget what the recipe was since it was a long time i had made one (about 2 years or so).anyway,thanks!!! :)lol
I had some time to make the cake so I marinated the pineapple in spicy rum and used the mixture of pineapple juice and rum to add to my cake mix. Used a mixture of dark cherries and marischino (sp) cherries and topped it with whipping cream. So good! Also, I agree that the pineapple upside down cake mix is good. Just make a few adaptations to it for my taste and used Irish Unsalted butter.
Best Pineapple Cake ever…!!!