We unpack the age-old connection between cast iron and upside-down cake.

We know it well: the glistening rings of canned pineapple, the candy-red maraschino cherries, all placed like a mosaic pattern.

Upside-down cake has been a ubiquitous presence at parties and potlucks since the middle of the last century, and the staying power of this charmingly retro dessert comes as no real surprise: a simple, sweet recipe rooted in little more than butter, brown sugar, and tropical fruit. 

But unbeknownst to many, except those few who continue to cook it like their mothers and grandmothers, upside-down cake has been around for much longer than the 1950s, and it has deep ties to cast iron, too.

Long before Betty Crocker or Duncan Hines, these inverted cakes were a common confection in Europe, dating back to the Middle Ages, and they were carried over to America by early colonists. Well into the 19th century, many of the original versions were cooked using cast-iron spiders, aka cauldrons with legs that stood over an open flame. As home ovens came into vogue in late 1800s, new flat-bottomed cast-iron cookware emerged, thus yielding “skillet cakes,” with their key ingredients ranging from cherries to prunes to apples (see the classic French tarte Tatin).

Up until the end of World War I, pineapple was still a rare, exotic, and expensive fruit in America. But by the 1920s, James Dole and his then-Hawaiian Fruit Company began to hit their stride, and as story has it, they would have a hand in cementing the national-treasure status of this now-iconic cake.

Around 1925, Dole invented the pineapple ring cutter, and to boost popularity of their new product, they kicked off a contest for recipes using the fruit. Some 2,500 pineapple upside-down cake iterations were submitted, and the next year, Dole ran an ad campaign based on the dessert, now dubbed an “upside-down cake.”

By the 1930s, these tropical treats would become one of the most popular dishes in American homes, a staple at bake sales and church luncheons, with red and green cherries even making an appearance at Christmastime. They would reach their peak in the 1950s, when boxed cake mix became widely available at supermarkets.

This was around the time that Barbara Greenwood of Baltimore first fell in love with upside-down cake. “My dad used to bake, and when I was a kid, that was the one cake where we didn’t have to stop what we were doing and run through the kitchen to make it drop for him,” she says today, now 66. “And oh, my goodness, it was so pretty and brown and buttery when it came out."

Eventually, Barbara would learn to bake the cake herself and start making it for her own son, spicing up the classic recipes by adding pineapple juice to the batter. “There’s science, sure, but there’s some magic, too,” she says. “There are some secret ingredients, a little bit of this, a little bit of that, that nobody will ever know.”

Except Carlos. 

“I remember standing in the kitchen, watching her bake, just fascinated by how the whole process came together,” he says today, now 47. For a kid, it was like a magic trick when she flipped the pan to reveal that colorful, caramelized surface, and though his father was a baker by profession, it was with his mother, a home cook and single mom, where he found his love of baking.

In fact, by the time he was 10, Carlos had started saving the tips he earned helping old ladies carry their grocery bags to their cars at the local Food-A-Rama. After his shift, he’d walk the aisles and fill his own cart with familiar ingredients: sugar, butter, pineapple.

“At first, I wanted a cake for myself, to see if I knew how to make it,” he says. “But on that first try, one of my neighbors was in the hallway—Miss Mabel—and she said, ‘Oh, it sure smells good in there, what are you making?’ I gave her a slice, and shortly after, she asked if I could make her a cake, which turned into her telling someone else about it down the street. Before I knew it, I was making cakes from the change I made at the grocery store and selling them around the neighborhood. It was just a matter of time before my mom was wondering why her gas and electric bills were going up. Because while she was at work, I was using the oven to bake.”

By the 1970s, when Carlos was born, cast iron had largely fallen out of fashion, particularly in urban areas, and both he and his mother used the lighter, less expensive option of aluminum to make their version of skillet cake. 

“It was big silver frying pan with a broken handle,” says Barbara. “But my dad used a cast-iron frying pan, and that pan just made everything better. It made chicken better, it made steak better, it made fish better. And I tell you what, those cakes, just the bottom layer, the brownness, the inside, everything about it, was thanks to the cast iron. I wish I still had that pan today.”

In full circle, Carlos, who now owns his own plumbing company, still bakes those cakes, but now, like his grandfather, he uses cast-iron to do so, for the same reasons his mom remembers. “The finish—that golden-brown glaze,” he says. Like with cornbread, that thick black metal affords a slow transfer and even distribution of heat to caramelize the sugars without burning the butter for a tender, golden crust. On top of that, the medium makes the cake easy to remove, as a seasoned cast iron, its porous surface impermeably bonded with oil, is virtually nonstick.

Of course, like for the rest of us, it might have something to do with nostalgia. “Just knowing that it comes from generations of my family, and that my mom taught me how to bake it makes it special,” he says.