Exploring Pineapple Upside-Down Cake (With Recipes)

Updated on April 2, 2020
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Linda explores food facts, folklore, and fabulous recipes, one ingredient at a time.

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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!

Recipes

Easy Pineapple Upside-Down Cake From Scratch
Easy Pineapple Upside-Down Cake From Scratch | Source

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 | Source

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 | Source

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.

Pineapple and Vanilla Cake
Pineapple and Vanilla Cake | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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 | Source

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.

Comments

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    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Mary, I agree the original is great, but . . . there's just so much imagination here. I'm kinda leaning toward the poke cake.

    • Blond Logic profile image

      Mary Wickison 

      7 months ago from Brazil

      I've just changed my tune. I started off thinking, "You don't mess with a good old fashioned Pineapple Upside Down cake.". My mother used to make her's in a cast iron skillet.

      As I kept scrolling down the page, Wow, they didn't just tweak it, they reinvented it . So many clever ways to try it. Thanks

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Sha, you could bake a different one each month and still not be through the list. I had fun compiling this one (and managed to not gain any weight, thank goodness!).

    • bravewarrior profile image

      Shauna L Bowling 

      7 months ago from Central Florida

      Linda, when I was pregnant with my son (many moons ago), I baked all the time. One of my favorites was the pineapple upside down cake, which I baked in a cast iron skillet. Very easy cake to make.

      The other variations in this article look yummy, too. The bundt pan version is beautiful! The pineapple poke cake has my attention. It looks incredibly moist and decadent.

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      My dear Manatita, I think glutton sounds far too harsh. Let's just say that you don't play favorites (you love them all) so there are no hard feelings.

      Happy New Year to you.

    • manatita44 profile image

      manatita44 

      7 months ago from london

      Wow! A lot here! Now we talking! I'll eat them all, gluten or no gluten! Ah, I'm a glutton. Is that how it's spelt?

      These recipes look awesome! Actually, I don't recall seeing the fudge. Happy New Year!! I'm coming 'round for dessert.

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Peggy it's nice to have those memories to hold onto.

    • Peggy W profile image

      Peggy Woods 

      7 months ago from Houston, Texas

      Reading this made me remember my mother's cast iron pan pineapple upside-down cake. It was spectacular! Thanks for the memories as well as other ways of making it.

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Miss Dora, I hope to do more to spread love and joy in 2020.

    • MsDora profile image

      Dora Weithers 

      7 months ago from The Caribbean

      What a treat you have given for a new start in the New Year. Vegan and gluten-free recipes mean that there is a version for everyone. Thank you very much.

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Thank you so much Audrey. We do best what we love. Happy New Year to you.

    • vocalcoach profile image

      Audrey Hunt 

      7 months ago from Idyllwild Ca.

      I'll trade you vocal and piano lessons for a few of your cooking lessons. :) My gosh, these recipes are amazing! f May your New Year bring you much happiness and love.

      Audrey

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Doris, you have just made me smile. I'm trying my best to provide gluten-free and vegan options in my articles. I'm glad this one gives you something to look forward to.

    • MizBejabbers profile image

      Doris James MizBejabbers 

      7 months ago from Beautiful South

      Did I just die and go to heaven? Linda, this article just kept getting better and better, especially when I got to the gluten-free cake and the cheesecake. (I shouldn't eat cheesecake because I'm very sensitive to dairy and find that it gives me body aches, but I'm going to do that one anyway.) I must bookmark this article because both Larry and I love pineapple upside down cakes. My mother made the best ones from scratch, but I can't find her recipe. I'll just try out yours. Thank you so much!

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Bill, pineapple cake is a tad too sweet for me, so believe it or not, we're on the same side of this argument. I'll talk to you next year.

    • billybuc profile image

      Bill Holland 

      7 months ago from Olympia, WA

      There will be no exploration here, thank you very much, but there will be a wish for a Happy New Year, and a big old thank you for your friendship.

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Flourish, even gluten-free or vegan is a no-no? I'm sorry. Yes, I'll add lemon to the list. Lemon meringue was always my Dad's favorite, and Mr. Bill loves lemon bars.

    • FlourishAnyway profile image

      FlourishAnyway 

      7 months ago from USA

      You have me wishing I could eat these (especially that last recipe), but my doctor put me on a very strict diet. I can dream, can't I? My grandmother and parents are fans of pineapple upside down cake, so maybe I'll make it for them and live vicariously. You might consider for a future article a collection of lemony desserts (lemon squares, lemon meringue pie, etc.).

    • Carb Diva profile imageAUTHOR

      Linda Lum 

      7 months ago from Washington State, USA

      Pamela, I had no idea how many wonderful ideas were out there; it was a pleasant surprise for me too. I'm glad you like it.

    • Pamela99 profile image

      Pamela Oglesby 

      7 months ago from Sunny Florida

      I love, love, love pineapple upside down cake. I think you have written about every possible wonderfukl pineapple dessert. I am going to check out a couple of these recipes. So, thank you Linda for this information.

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