The History of Pineapple Upside-Down Cake
Upside-down cakes have a history dating back to the Middle Ages, when cakes baked in skillets over the fire and inverted were much more reliable than oven technology. But it wasn’t until the 1920s, when canned pineapple became widely available and therefore all the rage, that pineapple upside-down cakes got their chance to shine. It’s unclear who first tried putting pineapple in a skillet cake, but a 1925 pineapple recipe contest sponsored by the Hawaiian Pineapple Company (now Dole) is credited with putting the dish on the national stage. Of over 60,000 recipes received, 2,500 submissions were pineapple upside-down cake. Hawaiian Pineapple Company noticed the trend and made the fruity dessert the center of a national ad campaign. By the 1950s, pineapple upside-down cake was a beloved classic found at potlucks and barbecues across the U.S. So how do you make a pineapple upside-down cake? Well, it obviously starts with pineapple. Traditionally, the cake starts with spreading some kind of caramel sauce in the bottom of a skillet or cake pan. Pineapple slices are arranged in the sauce at the bottom of the pan, then topped with cake batter and baked. After the cake comes out of the oven, it’s flipped out of the pan so that the caramelized pineapples are displayed on top. It’s a beautiful and delicious treat that doesn’t require any frosting or extravagant decorating. For this Cookbook Showdown, I tested four of the best pineapple upside-down cake recipes in popular cookbooks. One is classic, one adds a nutty twist, and two get a boozy boost from added liquors. Ready to find out which upside-down cake came out on top? Appearance: 4/5 — It looks very classic with its pineapple rings and maraschino cherries. The cake stuck a bit to the inside of the pan, but a little parchment paper could have saved it.Taste: 4/5 — This is exactly the flavor I expect from a pineapple upside-down cake, and the sour cream in the cake gave it a delicious texture and taste.Difficulty: Easy — The recipe is accessibly written for experienced bakers and newbies. Rather than modern twists on classics or unexpected flavor combinations, Cheryl Day focuses on sharing tried and true recipes and techniques. Her pineapple upside-down cake recipe is exactly what I imagine when I picture the dessert, with a buttery brown sugar topping, pineapple rings, and maraschino cherries atop a vanilla cake. But did it turn out as pretty as the picture? Appearance: 3/5 — I mean, you can tell what it is, but it’s not particularly pretty! The chunks of pineapple on top simply don’t have the same visual appeal as rings.Taste: 3.5/5 — The tequila flavor could have been more prominent, but it was present. Otherwise, this was very typical of the flavors one would expect.Difficulty: Easy — This is a great place to start if you’re new to pineapple upside down cakes. It’s easy to follow and flipped out of the pan cleanly. For this Cookbook Showdown, I tested Baker’s “Bottoms Up” Pineapple-Tequila Cake. It’s a mostly classic recipe, with the addition of three tablespoons of tequila, one in the brown sugar topping and two in the cake itself, meaning the majority of the alcohol bakes out. How did this boozy twist on a classic turn out? The second concern I had was the instructions for the cake. There’s a certain order of operations that bakers tend to follow when making a cake: cream the butter and sugar together and then add eggs, mix the dry ingredients together in a separate bowl, and slowly incorporate the dry ingredients to the butter, adding milk or another liquid in between. There are many reasons you start with creaming the butter and sugar, partially to control the temperature and texture of the butter. Taylor’s recipe called for mixing the butter with milk and eggs, and adding the sugar to the dry ingredients, then mixing it all together. Against my better judgment, I followed the instructions, and the butter ended up clumpy, making for an inconsistent batter. The recipe also called for a 60 minute bake time at 350 degrees Fahrenheit, which I knew was far too long even for my slow oven. I ended up baking it for about 35 minutes, which was just right. When I saw Taylor’s Pineapple Black Walnut Upside Down Cake, I knew I had to give it a try. The black walnut sauce is a creative way to add complex flavors and a little crunch to a classic cake. Let’s take a look at what happened when I gave this recipe a try. Appearance: 3/5 — It looks fine, but a little rough around the edges.Taste: 2.5/5 — I think these flavors have a lot of potential together, but the black walnut sauce was a difficult texture after the reheating debacle, and the cake could have used some additional flavoring.Difficulty: Moderate — Nothing about this cake is too difficult on its own, but the entire thing would be easier if the instructions followed a more familiar process and included more detail. Appearance: 4.5/5 — The whipped cream, toasted coconut, and cherry toppings are visually appealing, and the bright blue swirl is a great touch.Taste: 4.5/5 — These were absolutely delicious! They were a little sticky from the toppings and rum sauce, but I certainly don’t mind a finger-licking cupcake.Difficulty: Moderate — This recipe requires several different techniques, but they can be simplified by using untoasted coconut and store bought whipped cream. They were also a little tricky to get out of the cupcake pan. The pineapple cake in this cookbook came from the cake shots section: Blue Hawaii Pineapple Upside-Down Cupcakes. It’s a mashup of the classic cake and a Blue Hawaii Cocktail, with blue Curaçao, rum, and sweet and sour mix included. Each cupcake has a swirl of blue cake colored with the Curaçao, a ring of pineapple, rum-spiked whipped cream, toasted coconut, and a cherry on top. They’re colorful and brimming with tropical flavors. Here’s how they turned out.
Fresh vs. Canned Pineapple: Most recipes I tested said either fresh or canned fruit was fine. I opted for fresh in all cases but the cupcakes. Using fresh pineapple takes longer to prep and can be a little tougher to cut with a fork while eating the cake, but also lends a stronger pineapple flavor. In either case, be sure to pat your pineapple slices dry to avoid adding too much liquid to the cake. Getting the Perfect Bake: I found that these cakes fared better — especially over time — if they were cooked a little longer than I would normally prefer. The pineapple retains moisture, so if the cake isn’t thoroughly baked, it will get gooey as it sits out. Wait until your cake starts to turn a light golden brown before taking it out of the oven. Careful with the Caramel: Most pineapple upside-down cakes involve making a brown sugar and butter caramel sauce to spread in the bottom of the dish with the pineapple slices. If you’re nervous about making caramel, this is actually a low-stakes place to practice, since baking it with the cake is pretty forgiving. But it does get VERY HOT, so be careful not to splash yourself in the process! And I recommend spreading the caramel immediately in your baking dish when it comes off the stove, as it might solidify as it cools (like in the recipe from The Up South Cookbook).
Alright, let’s get to the good stuff! The winner of this Cookbook Showdown is…
Winner: Cheryl Day’s Treasury of Southern Baking — Pineapple Upside-Down Cake
This classic recipe has exactly the look and flavors I expect from a pineapple upside-down cake, and its written in an approachable way. This cake is a crowdpleaser with textures and flavors that let the pineapple shine. I whole heartedly love this recipe. But there’s another recipe that I can’t let go…
Honorable Mention: Krystina Castella and Terry Lee Stone’s Booze Cakes — Blue Hawaii Pineapple Upside-Down Cupcakes
These adorable cupcakes earn an honorable mention for best twist on the classic dish. The swirl of blue color, added flavors of rum and blue Curaçao, and multiple toppings made these sweet treats unforgettable. If you’re baking for folks who love a tropical cocktail, these cupcakes are a must-bake. Find out what cookbooks impressed us the most in these past Cookbook Showdowns:
Cookbook Showdown: Chai Cookbook Showdown: Ginger Cookies Cookbook Showdown: Hot Chocolate Cookbook Showdown: Pumpkin Pie
