Skip to main content

Exploring Pineapple Upside-Down Cake (With Recipes)

Linda explores food facts, folklore, and fabulous recipes one ingredient at a time.

exploring-pineapple-upside-down-cake

A Treat for Only the Rich and Famous?

When Christopher Columbus made his second voyage to the New World, he anchored his ship off the island of Guadalupe. It was there that he discovered the fruit that he named “pina de Indes.” Sixty years later, pineapples were being exported from the Western Hemisphere to Europe but they were a food of the elite. The pineapple was and is delicate and perishable and, in the rule of supply and demand, it became a luxury of kings rather than food for the common man. The pineapple became the exotic fruit of the rich, or quasi-rich. Believe it or not, pineapples were “rented” for display on banquet tables, not for consumption, but merely as a symbol of the wealth of the host.

It wasn’t until 1920, when the Dole Pineapple Company began commercial production and canning of pineapple, that the fruit became accessible to everyone. Most food historians agree that it was not until then that the pineapple upside-down cake became a possibility. Although cakes baked with fruit were not a new innovation (consider the French tarte tatin), the use of pineapple in a cake is definitely a 20th-century invention.

While rooting around in old women's magazines I found a Gold Medal Flour ad with a full-page, four-color picture of Pineapple Upside-Down Cake—a round cake with six slices of pineapple, candied red cherries, and a brown sugar glaze. The date: November 1925.

— American Century Cookbook: The Most Popular Recipes of the 20th Century, Jean Anderson (p. 432)

The Original Recipe

It was also in 1925 that the Dole Pineapple Company published an advertisement seeking innovative pineapple recipes. The Food Timeline reports that over 2,500 recipes for pineapple upside-down cake were submitted for consideration.

I found what is purported to be the original recipe at Wikibooks.

Can we do better than this? Can we create an even better cake, and then use that flavor profile to create even more delectable recipes? Yes, we can!

Easy Pineapple Upside-Down Cake From Scratch

Easy Pineapple Upside-Down Cake From Scratch

Easy Pineapple Upside-Down Cake From Scratch

The pineapple upside-down cake is, when you think about it, a gift to anyone who wants to present a "wow" dessert without hours of toil and/or a culinary degree in baking. The cake bakes in one pan. There is no multi-tiered terror of "will it slide apart" drama, no frosting, no filling. There is no whipping of egg whites or concoctions simmered over a double-boiler. It is a simple one-bowl yellow cake, baked atop fruit layered in the bottom of a cake pan—and the end result is absolutely stunning!

Meghan Splawn shares with us a homemade recipe that even the novice baker can achieve with her recipe for pineapple upside-down cake from scratch.

Cast Iron Pineapple Upside-Down Cake

Cast Iron Pineapple Upside-Down Cake

Cast Iron Pineapple Upside-Down Cake

Kat is a mother of three boys; she loves to bake and enjoys all things DIY. She has been blogging since 2010 featuring recipes and home design projects. Some of her home projects have been featured in Country Living and This Old House magazine. This cast-iron skillet pineapple cake is made the way that cooks made cakes years ago. The brown sugar forms a rich caramel-like syrup that your friends and family will love.

Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

What's better than a slice of pineapple upside-down cake? What about a cake that you don't have to share? These baby pineapple upside-down goodies are even easier because they are made with a box of yellow cake mix.

Scroll to Continue

Read More From Delishably

Pineapple and Vanilla Cake

Pineapple and Vanilla Cake

Pineapple and Vanilla Upside-Down Cake

This pineapple and vanilla cake by Donna Hay takes the concept of an upside-down cake in a totally different direction. Fresh pineapple slices are poached so that they become pliable and create this stunning work of art. It's almost too pretty to eat.

Pineapple Upside-Down Dump Cake

Pineapple Upside-Down Dump Cake

Pineapple Upside-Down Dump Cake

Dump cakes are by far the simplest dessert in the world; take just five ingredients and dump them into a cake pan. No mixing or stirring, no separating eggs or beating butter and sugar until fluffy. Dump, bake, done. This pineapple version has all of the flavors of the traditional upside down cake without the fuss.

Serve it warm with a scoop of vanilla ice cream. Yum!

Pineapple Monkey Bread

Pineapple Monkey Bread

Pineapple Monkey Bread

In April 2018 I wrote an article about the history of monkey bread—a quirky name for a seriously delicious sweet bread. Just now I did a Google search on "monkey bread recipe." Would you believe 22,900,000 hits?

This recipe for pineapple monkey bread is made even simpler with the use of canned refrigerated biscuits (if those are not available where you live, I'm pretty confident that you could use your own biscuit recipe). Dessert for breakfast? Why not.

Pineapple Upside-Down Cheesecake

Pineapple Upside-Down Cheesecake

Pineapple Upside-Down Cheesecake

The kitchen wizards at Kraft Foods have developed a cheesecake with pineapple rings and cherries in the graham cracker crust. Some people who rated the recipe reported that they had problems with the pineapple sticking to the bottom of the pan; I'd recommend lining with parchment paper.

Vegan Pineapple Upside-Down Cake

Vegan Pineapple Upside-Down Cake

Vegan Pineapple Upside-Down Cake

I have a friend who is vegan (no butter or eggs used in baking), so I found this vegan upside-down cake for her. It looks perfectly moist and rich and relies on ingredients that you probably already have in your pantry.

Gluten-Free Pineapple Upside-Down Cake

Gluten-Free Pineapple Upside-Down Cake

Gluten-Free Pineapple Upside-Down Cake

Sha is a gluten-free recipe developer and author of The Gluten-Free Quick Bread Cookbook. Her mission in life is to teach us how to make and bake the best gluten-free treats, baked goods, and breads—so good that your gluten-eating friends will be jealous. Her upside-down cake is made with gluten-free all-purpose flour and is adapted from a recipe found at Sally's Baking Addiction.

Pineapple Upside-Down Cake Sugar Cookies

Pineapple Upside-Down Cake Sugar Cookies

Pineapple Upside-Down Cake Sugar Cookies

I hope you've not grown weary of this topic, cuz we're not done yet. Sugar cookie meets pineapple upside-down cake, they fall in love and create this sticky, gooey, finger-licking treat that you can bake any time of year.

Pineapple Upside-Down Doughnuts

Pineapple Upside-Down Doughnuts

Pineapple Upside-Down Doughnuts

Pineapple rings have a hole in the center. Doughnuts have a hole in the center. It just seems logical to put the two of them together, doesn't it? Liren uses a doughnut pan to bake these pineapple upside-down doughnuts (easier and healthier than frying).

Pineapple Upside-Down Cake Fudge

Pineapple Upside-Down Cake Fudge

Pineapple Upside-Down Cake Fudge

I used to avoid candy-making; the prospect of boiling sugar to the proper stage gave me nightmares. Thank goodness someone developed marshmallow creme (aka fluff). Creamy fudge is now a breeze to make and this recipe for pineapple upside-down fudge won't disappoint.

Pineapple Bread Pudding

Pineapple Bread Pudding

Pineapple Bread Pudding

This pineapple bread pudding is absolutely fabulous, but not for the weak of heart. It could kill you, but what a way to go. I mean, any dessert that includes a loaf of brioche, 2 1/2 cups of brown sugar, 4 eggs, a quarter pound of butter, and almost 3 cups of heaving whipping cream certainly gets my attention.

Campfire Upside-Down Cake

Campfire Upside-Down Cake

Campfire Pineapple Upside-Down Cake

Just because you are cooking over a campfire that doesn't mean that dessert has to be s'mores. Step up your game; become the king or queen of the campground with this bake-it-in-a-Dutch-oven pineapple cake that cooks over the coals.

Pinapple Pancakes

Pinapple Pancakes

Pineapple Pancakes

If you have a sweet tooth like my husband and daughter, I'm sure you'll love these pineapple upside-down pancakes. Simply pour the batter; when you see bubbles begin to form and the edges firm up, then top with the pineapple rings and cherries. Flip, cook a minute more and dive in.

Pineapple Upside-Down Bundt Cake

Pineapple Upside-Down Bundt Cake

Pineapple Upside-Down Bundt Cake

Like me, Jen often uses the website Pinterest for inspiration. Her pineapple upside-down cake in a bundt pan is one of those moments of genius. Isn't it pretty? It looks like you fussed for hours and, if no one else but you and I read this post, it will be our secret.

Pineapple Poke Cake

Pineapple Poke Cake

Pineapple Poke Cake

In 1969 the Jello gelatin company invented the first poke cake recipe and since then hundreds of iterations have appeared on the internet. This pineapple poke cake is so easy—it's spongy, moist, sticky, and gooey and fills a 9x13-inch baking pan. That's enough for your next potluck dinner.

Related Articles