Best Ever Pineapple Upside Down Cake (and a Bit of History)

April 20th is one of our favorite days of the year. Not because of the common associations, but because it’s National Pineapple Upside Down Cake Day.

Pineapples are known for symbolizing hospitality, friendship, and generosity, so there’s truly no better way to welcome guests into your home (or any excuse, really) than with this delicious treat. We’re sharing a bit on where this cake came from, and the best ever pineapple upside down cake recipe.

A Short History of Pineapple Upside Down Cake

The origins of the pineapple upside down cake date back hundreds of years, when people would cook on cast-iron skillets over open fires. When they wanted a sweet treat, they would line the bottom of the pans with fruit, and pour batter on top. When the cake was ready, the pan was flipped over, revealing the gorgeous pattern of caramelized fruit on the top.

Early Americans used cast-iron skillets with legs on the bottom to make these cakes. The skillets were called, “spiders,” and thus the cakes were called, “spider cakes.” When technology advanced and the home oven became a reality and a mainstay of kitchens, a transition to flat-bottomed cast-iron skillets (the same as what we use today) emerged as the new way to bake cakes. These skillets were used to make the same “spider cakes,” but in an oven.

And in the very early 1900s, James Dole (founder of the Hawaiian Pineapple Company, now known as Dole) created the perfect way to can pineapples, which had not been a reality before this point. Pineapple made its way into more and more American homes this way, and at some point, the pineapple upside down cake was born.

A Unique Twist on an Old Recipe

And with spring and summer here in the DC area, incorporating a bit of a tropical twist to your dessert menu is always an excellent idea. Add to it a very special secret ingredient (shhh… it’s rum!), you’ll be transported to the tropics upon first bite, imagining the warm sea breeze running through your hair and hearing the ocean waves crashing at your feet. Okay, maybe that’s a tall order for a simple cake, but trust us, between the pineapple and the rum, and the ever-so-sweet golden brown caramelized topping, you will be in absolute heaven.

We hope you love this recipe for the best ever pineapple upside down cake as much as we do. If you give it a try, let us know how you like it!

Best Ever Pineapple Upside Down Cake

Recipe via Food Network

Ingredients

1 12-ounce package of frozen cherries, thawed
3/4 cup spiced rum (we’re fans of good old Captain Morgan, but if you really want a tropical twist, try a coconut rum)
2 sticks unsalted butter, room temperature
3/4 cup sugar
5 eggs
2 teaspoons vanilla extract
1 1/2 cups all-purpose flour
1 teaspoon salt
3/4 teaspoon baking powder
1 tablespoon dark brown sugar
1 pint creme fraiche
1 lime, zested
1 orange, zested

Directions

1. In a medium bowl, add the cherries and the spiced rum. In another bowl add
   the pineapple and the 3/4 cup of rum. Cover and refrigerate for 8 hours or
   overnight.
2. Preheat oven to 350 degrees F.
3. In a large bowl, add 1 3/4 sticks butter and the sugar and cream together until
   pale yellow, about 2 minutes. Stir in the eggs 1 at a time. Add the vanilla
   extract and set aside.
4. In a separate bowl, combine the flour, salt, and baking powder. Add the dry
   ingredients into the wet ingredients and stir until a smooth batter forms.
5. In a 10-inch cast iron skillet, over medium heat, add the remaining 1/4 stick
   butter and heat until the butter has just melted. Add the brown sugar and using
   a slotted spoon, add the pineapple pieces, reserving the rum. Saute until they begin
   to caramelize, about 4 minutes. Add the cherries and the rum they soaked in.
6. Remove the skillet from the heat and light the rum with a long kitchen match. When
   the flames subside, return the pan to the heat and cook until most of the alcohol has
   evaporated. Remove the skillet from the heat and set aside to cool 6 to 10 minutes
   before adding the batter. Remove half the fruit back into the reserved rum for
   garnishing later.
7. Add the batter to the skillet and put in the oven. Bake for 30 to 45 minutes or
   until a toothpick inserted into the center comes out clean. Remove from the
   oven and set aside to cool for about 5 minutes before unmolding. To unmold, run a
   small knife around the edge of the cake, take a large serving plate and put it over the
   cast iron skillet. Carefully flip over and let sit for a couple of minutes until it releases
   from the skillet.
8. Put the creme fraiche in a small bowl and stir in the zests. Cut the cake into
   wedges and serve with a dollop of creme fraiche and the reserved fruit.

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