Retro Classics: Pineapple Upside-down Cake


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The recent cold snap has had many of us scrambling to the kitchen for any excuse to turn on the oven and daydream of sandy beaches and pineapple palms. So the next time you turn on the oven, why not take a trip in the time machine back to the fifties and sixties, the golden age of pineapple upside-down cake, a retro classic that is great any time of year.

This iconic dessert is a variation of what used to be called “skillet cakes’, cakes that were made in a cast iron pan. Traditionally the topping of the cake-seasonal sliced fruit or berries and or nuts and butter and brown sugar that will form a glaze- is put into the pan first, then the batter is poured over and the cake is baked. After baking, a plate is placed over the pan, and the pan is flipped over. The topping is glorious; the fruit is transformed, shimmering and caramelized, and the glaze from the melted sugar and butter and fruit juices seep into the cake.

Though skillet cakes had been around for ages, it wasn’t until the onset of the twentieth century that the pineapple version came along. A certain Jim Dole, founder of what is now known as the Dole Food Company, started canning pineapples. In the twenties, to drum up sales, the Hawaiian Pineapple Company, as it was called then, sponsored a contest to determine the best pineapple recipes. The contest attracted over 2,500 recipes for pineapple upside-down cake, and a classic was born. The combination of pineapple and maraschino cherries had a real grip on North Americans in the years following WW2, adorning dishes both savory and sweet, and this cake became a standard.


There's a ham under there somewhere....

There’s a ham under there somewhere….


Food fashions come and go. You don’t really see this cake much anymore, likely due to the fact that canned fruits and vegetables are not exactly in vogue. And don’t get me started on maraschino cherries. But it is still a much-loved dessert, and still baked by countless home cooks, many of whom grew up on it. You could make it with real, fresh sliced pineapple, and maybe real cherries, but it is doubtful that it would have the same appeal. And it’s not difficult to find a recipe. We made it the other day using Trisha Yearwood’s recipe. Why Tricia Yearwood? Who knew the country and western warbler was also a whiz in the kitchen? And it just so happens her recipe is made with an 8×8 square pan, which is what we wanted to use, as it was a good size and guaranteed nine perfect little pieces, each with a perfectly glazed pineapple ring, purchased just for this occasion. We didn’t use maraschino cherries though, opting instead to fill the pineapple hole with a blob of raspberry jam.

Whether you consider it retro, or dated, or classic, it doesn’t matter. This cake is amazing. Super simple to make, the crumb is delicate and velvety and moist, and the presentation is guaranteed to bring a smile to your face. Here is Trisha Yearwood’s recipe if you want to have a go at it. But, like most of us, you’ll probably have to add a can of sliced pineapple and a little jar of maraschino cherries to your shopping list first!


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