Cookbook Showdown: The Best Pineapple Upside-Down Cake Recipes

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Susie Dumond

Senior Contributor

Susie (she/her) is a queer writer originally from Little Rock, now living in Washington, DC. She is the author of QUEERLY BELOVED and the forthcoming LOOKING FOR A SIGN from Dial Press/Random House. You can find her on Instagram @susiedoom.

Welcome back to Cookbook Showdown, where we test four recipes for the same dish from different popular cookbooks to find out which recipe comes out on top. Today, we’re testing recipes for a beloved American classic: pineapple upside-down cake. These recipes range from classic takes to creative boozy twists, but which fruity dessert will reign supreme? Read on to find out!

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?

Cookbook Showdown: Pineapple Upside-Down Cake

Cheryl Day's Treasury of Southern Baking cookbook cover

Cheryl Day’s Treasury of Southern Baking by Cheryl Day

Cheryl Day is an acclaimed baker, owner of Back in the Day Bakery in Savannah, Georgia, and co-founder of Southern Restaurants for Racial Justice. She’s also the great-granddaughter of an enslaved pastry chef. Day’s Treasury of Southern Baking is a remarkable cookbook packed cover-to-cover with hundreds of classic Southern recipes, and it pays special homage to the enslaved cooks and bakers who shaped our idea of American cuisine.

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?

The Process

Day’s recipe includes thoughtful, well written instructions and easy to find ingredients. Instead of milk or buttermilk, Day calls for sour cream, which gives the cake a velvety texture and tangy flavor. The cake is baked in a rectangular pan rather than a round cake pan or skillet. I was pleased to find that the process went almost exactly as described in the cookbook, and the result is worthy of any Southern potluck.

The Results

Image of a rectangular pineapple upside-down cake with six pineapple rings and maraschino cherries on top, sitting on a wooden cutting board in front of Cheryl Day's Treasury of Southern Baking cookbook
Pineapple Upside-Down Cake made from Cheryl Day’s Treasury of Southern Baking. Source: Susie Dumond

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.

The Boozy Baker by Lucy Baker book cover

The Boozy Baker: 75 Recipes for Spirited Sweets by Lucy Baker

Written by Serious Eats columnist Lucy Baker, this cookbook has a wide variety of baked goods infused with spirits and liqueurs. Even better, some of the desserts are paired with suggested cocktail recipes. It includes cakes like Southern Comfort Red Velvet Cake, pies and tarts like Margarita Meringue Pie, fruit treats like Boozy Bakes Apples, and more. You may have seen Hard Cider Apple Pie from The Boozy Baker as a serious contender in Book Riot’s Apple Pie Cookbook Showdown.

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 Process

The cake recipe is very standard here, with a little tequila added for flavor. Something I loved about this recipe is that it instructs you to melt down the brown sugar, butter, and tequila on the stove in the cake pan you’ll use to bake the cake. Although I may not traditionally use my cake pans on the stove, it worked out really well and saved me from extra dirty dishes. After melting down the topping, you simply arrange chunks of fresh pineapple in the bottom of the pan and proceed to make the cake.

The Results

Image of a round pineapple upside-down cake with chunks of fresh pineapple on top. The cake is on a rainbow cake plate in front of The Boozy Baker cookbook.
“Bottoms Up” Pineapple-Tequila Cake made from The Boozy Baker. Source: Susie Dumond

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.

The Up South Cookbook cover

The Up South Cookbook: Chasing Dixie in a Brooklyn Kitchen by Nicole A. Taylor

Nicole A. Taylor grew up in Georgia and spent a chunk of her life trying to distance herself from her Southern roots. But after moving to Brooklyn, she was reawakened to the magic of Southern cooking. In this cookbook, she blends family recipes, Southern classics, and her new Brooklyn sensibilities for a deeply personal collection of food. Dishes like Squash and Tomatillo Grits, Smoked Trout Deviled Eggs, and Collard Green Pesto and Pasta put a fresh spin on familiar flavors. It’s also got crucial instructions for staples like chicken stock, pimento cheese, and iced tea.

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.

The Process

Looking at the ingredients for this recipe, I knew it had something going for it. The black walnut sauce sounds delicious, it calls for fresh pineapple, and the rest of the cake recipe looked pretty classic. It wasn’t until I started reading the steps that I grew concerned. The recipe starts with making the black walnut sauce on the stove. Since the sauce is primarily brown sugar and walnuts, I worried it would turn into something like a hard candy if it cooled before going into the cake pan. That’s exactly what happened. By the time I reached the step to add the sauce to the cake pan, it was a brick. I tried softening it on the stove, which resulted in the edges burning, and eventually heated it in the microwave until it broke down enough to spread.

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.

The Results

Image of a round pineapple upside-down cake with a dark walnut sauce on a glass cake plate in front of The Up South Cookbook
Pineapple Black Walnut Upside Down Cake made from The Up South Cookbook. Source: Susie Dumond

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.

Booze Cakes by Krystina Castella and Terry Lee Stone cookbook cover

Booze Cakes: Confections Spiked with Spirits, Wine, and Beer by Krystina Castella and Terry Lee Stone

This spirited little cookbook is full of recipes for delicious cakes with boozy twists. Some of the dishes are classic cakes given an added dose of alcoholic flavor, like a German chocolate cake spiked with Jägermeister. Others are traditionally boozy cakes, like Tipsy Tiramisu. Other cake recipes take their inspiration from beloved cocktails, like Mint Julep Cupcakes. Cake shots, or bite-sized treats perfect for parties, are also included, like Long Island Iced Tea Cakes.

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.

The Process

This recipe has quite a few components for a cupcake. After making the cake batter, it asks you to separate some out and color it with blue Curaçao. It also includes steps to make a rum brown sugar topping to pour over the pineapples and spiked whipped cream. Toasting the coconut is an added step, but well worth it for the flavor and crunch. Although the recipe doesn’t clarify, I used canned pineapple rings to fit more neatly in my cupcake pan. They were a little messy to get out of the pan, but looked pretty cute by the time the toppings were in place.

The Results

Image of twelve cupcakes on a rectangular serving dish. Each cupcake is topped with a pineapple ring, whipped cream, cherry, and toasted coconut. The tray sits in front of Booze Cakes cookbook.
Blue Hawaii Pineapple Upside-Down Cupcakes made from Booze Cakes. Source: Susie Dumond

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.

Final Results

This was a grand adventure in caramel toppings and cake flipping. Here are a few lessons I learned in the process of this Cookbook Showdown:

  • 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.

square piece of pineapple upside-down cake with a maraschino cherry on a blue plate
Slice of Pineapple Upside-Down Cake made from Cheryl Day’s Treasury of Southern Baking. Source: Susie Dumond

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: