I recently received a comment on my blog asking about authentic 1920s desserts for a party. After a quick search, one treat kept appearing—Pineapple Upside-Down Cake. Its rise to popularity has a fascinating history, which I thought would make for a great blog post featuring vintage recipes and advertisements. Plus, this dessert holds a special place in my heart—my mom used to make it all the time, and it was a beloved favorite in our home. So, let’s dig in and have some delicious fun!
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What is Pineapple Upside Down Cake?
Super moist, cake that’s both soft, and perfectly fluffy, a pineapple upside-down cake is a delicious and festive one-layer cake dessert that gets assembled and baked with juicy pineapple slices and sweet cherries on the bottom, and vanilla cake batter on top. Turned upside down after baking, the glistening, now caramelized fruit, magically becomes the impressive cake topping (Source).
Brief History of the Pineapple Upside Down Cake
The earliest record of the term “Upside-Down Cake” appeared in 1923 in several sources, including the March 15, 1923 issue of the Syracuse Herald (p. 15), in a column entitled “Unusual Prune Dishes,” which, as the designation connotes, provided a version made with dried plums (and no mention of pineapple). At this early point, the recipe already featured a common element of classic upside-down cakes — fruit arranged atop a brown sugar syrup in an iron skillet (Source – incls a detail breakdown of the dessert & a recipe).
Around this time a few pineapple upside-down cake recipes were being published in small regional cookbooks. Pineapple consumption was on the rise thanks to cheaper prices and increased imports. The biggest reason for this change was James Drummond Dole’s cannery business in Hawaii, which started in 1901. Pineapple had been grown in Hawaii since the early 1800s, and there were canneries there by the 1880s, but none were on the scale of the Dole operation. Dole had a machine that could peel, core, and cut 100 pineapples per minute. Soon he and other Hawaiian growers were producing so much pineapple that they needed an advertising campaign to convince Americans to buy it all.
Then in 1925, the Dole company sponsored a recipe contest for the best dish using pineapple, and ran ads for it in women’s magazines. The winner was a pineapple upside-down cake from Mrs. Robert Davis of Norfolk, Virginia. Dole received more than 2,500 submissions for pineapple upside-down cake (out of 60,000 recipes total), so clearly some people were making a version of this cake prior to 1925.
In any case, the Dole company promoted Mrs. Davis’s winning recipe widely, and soon pineapple upside-down cake was one of the most popular cakes in North America (especially in the Mid-Century) (Source).
The winning 1925 recipe (FULL Recipe HERE).
Vintage Advertising & Vintage Dessert Recipes
1925 advertisement for GOLD-MEDAL FLOUR featuring the famous winning cake (not the actual cake). It is clear that advertisers were jumping on the band wagon of this win by making this yummy creation, front and center on their advertisements (in fact it’s not even mentioned in this ad).
1954 Bisquick advertisement. Betty Crocker’s team says that Bisquick is the new way to bake when making your Pineapple Upside-Down Cake.
I was gifted many moons ago a first edition 1950 Betty Crocker Cookbook and inside there is a recipe for a few different upside-down cakes. Not sure about the prune one, but the rest sound good.
Comment below with your email if you would like this sent to you (might not be clear on everyone’s screen).
1950s vintage advertisement for “Pineapple upside-down cakes done 3 different ways by DOLE”.
Source: Etsy-PlentifulPages
“For this Hawaiian Pie use Libby’s Peak Flavor Pineapple”. 1947 ad featuring a baking recipe for our pie (not cake) using gelatin.
Source: Pinterest
Here is the 1960s Betty Crocker’s New Picture Cook Book (1961) Upside-down cake recipes.
Source: Reddit
1950s / 1960s vintage advertisement for Dole Hawaiian Pineapple featuring different things you can make with Pineapple. Like Pineapple Upside Down Cake (baked in a ring mold) and Meat Loaf /Ham Loaf.
Source: Pinterest
I’m really excited about finding this next advertisement and recipe because it’s from 1943 and WW2 is in full swing and so is food rationing. This Dole ad talks about the food stamps and coupons everyone had and how this dessert is easy to make using them (recipe below). “Coupon Days Upside-Down Cake“.
While not the traditional cake recipe, this 1953 KRAFT advertisement features a Caramel Surprise Pineapple Upside-Down Cake recipe (with yummy Kraft Caramels).
1955 Karo Corn Syrup advertisement with the cake being in a rectangular shape as opposed to the famous round. Not sure how I feel about it. Do you like it this way?
I don’t know what year this Pillsbury advertisement is, but from the look of the image / ad maybe 1930s or 1940s? That is just a guess though, but I will say that I’m a big fan of the whip cream on this delicious cake.
Would you like the recipe? You can find it here.
Source: Vintage Recipes
1968 Duncan Hines advertisement for various Upside Down Cakes, like deep chocolate and a recipe for Double Pineapple Upside Down Cake (seen in the next image).
A 1950s recipe card (front) from ‘Standard Humpty-Dumpty and Super Markets’.
Source: Etsy-whokeepsthisstuff
“The Pineapple Cookbook- 12 favorite recipes from the Dole Kitchen”.
The key to the success of this cake is a good proper tin to make the magic happen (or so I have been told. Ha!). This 1970’s copper cake mold version was avail at time of posting on Etsy and would be perfect for the job.
Source: Etsy-CopperRestoration
Question time! Are you fan of this cake? Or have any memories around it (like I do)? Share any thoughts on this topic in the comments section below. I love hearing from my readers.
Further Reading: Vintage Food Posts (archived).
Thanks for dropping by!
Liz
