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Pineapple Upside Down Skillet Cake

by Lori on March 21st, 2011

A slice of pineapple cake, take three

If you want a pan that can do just about anything, get a cast iron one. It can fry a steak, sauté veggies, simmer a stew and even bake a cake! It does especially well with pineapple upside down cake. It bakes the cake evenly inside and creates a nice crunchy outside. If it is well-seasoned, the pan will even let the cake slide hassle-free from it. Now if only the pan could clean up after itself.

The Story

Ken’s grandpa (his dad’s dad) came to visit this weekend, which inspired me to make pineapple cake. The recipe I made came from Ken’s grandma (his mom’s mom). It was a huge hit. Both my husband and his grandpa quickly devoured their slices. His grandpa even asked for an extra slice to take home.

It would not have been possible without Ken’s mom. She helped save my cast iron pan from demise.
Cast iron skillet, take one

When I purchased my first set of cast iron pans, I didn’t know what I was doing. The ones I found were not pre-seasoned and still had a steel gray color. They came with instructions for seasoning, which said to coat them in vegetable oil and bake them in the oven. It sounded easy enough. However, when I pulled them out of the oven, I didn’t have beautiful black pans. I had a huge sticky mess. The oil created an uneven sticky film all over them. I thought they were ruined, but didn’t want to admit it. Discouraged and dismayed, I stuffed them in the back of the cupboard – putting them out of sight and mind.

The next time my mother-in-law visited, I pulled out my sticky pans to ask for advice. She has a beautiful set of cast iron pans, so I knew she would know what to do. She inspected them closely and gave her diagnosis. They would be OK. Her prescription to cure them of their stickiness was to just start using them. She recommended cooking lots of greasy things, like bacon. She said it would help to season them properly and over time the stickiness would go away. My husband was excited at the idea of frequent bacon eating. I was relieved there was a cure for my pans. Following her advice, I ended up with a happy husband and beautiful cast iron pans.

Skillet, take four

The Moral of the Story

Don’t believe everything you read – even instructions for seasoning a cast iron pan. If you have a seasoned cook in your family, ask them for advice instead.

Pineapple cake, take six

About the Recipe

This recipe was passed down to me from Ken’s grandmother. I’m not sure where she got the recipe originally, but it works like a charm every time. The dough reminds me more of a sugar cookie than a cake. The only change I made was adding a teaspoon of the cherry juice from the maraschinos to the  batter for a little extra cherry flavor.

The Cast of Characters

Pineapples take center stage

Pineapple and maraschino cherries are tops in this recipe.

The Play-by-Play

In an iron skillet over medium heat, melt the butter and shortening.
Melting butter and shortening, take one

Mix in the brown sugar until dissolved.
Brown sugar melted

Take off the heat. Arrange the pineapple slices in the mixture.
Adding the pineapple, take two

Now add the cherries, and let stand while mixing the dough.
Adding the cherries, take four

Sift together the flour, sugar, baking powder and salt.
Sifting the flour and sugar

In the stand mixer, add the flour mixture, shortening, milk, vanilla and egg.
Add eggs, cherry syrup and vanilla

Mix until well combined.
The batter comes together

Spread the dough over the pineapple slices and cherries.
Topping with batter, take one

Put the skillet in the oven.
Skillet cake in the oven

Bake for 10 to 15 minutes or until a toothpick inserted in the center of the cake comes out clean.
Skillet cake before the flip, take one

Place a large round plate on top of the skillet and turn upside down.
Pineapple cake, take one

Recipe: Grandma’s Pineapple Upside Down Skillet Cake

Summary: An old-fashioned skillet cake with pineapples and cherries

Ingredients

2 tablespoons shortening
2 tablespoons unsalted butter
1 cup brown sugar
7 slices of pineapple
12-15 maraschino cherries
1 ¾ cups flour
¾ cups white sugar
2 teaspoon baking powder
½ teaspoon salt
1/3 cup shortening
½ cup milk
¾ teaspoon vanilla
1 teaspoon maraschino cherry juice
1 egg

Instructions

  1. Preheat oven to 425 degrees. In an iron skillet over medium heat, melt the 2 tablespoons of butter and 2 tablespoons of shortening.
  2. Mix in the brown sugar until dissolved.
  3. Take off the heat. Arrange the pineapple slices and cherries in the mixture. Let stand while mixing the dough.
  4. Sift together the flour, sugar, baking powder and salt.
  5. In the stand mixer, add the flour mixture, shortening, milk, vanilla and egg. Mix until well combined.
  6. Spread the dough over the pineapple slices and cherries.
  7. Bake for 10 to 15 minutes or until a toothpick inserted in the center of the cake comes out clean.
  8. Place a large round plate on top of the skillet and turn upside down.

The Footnotes

  • About the cherries: I added a teaspoon of the maraschino juice to the cake batter for extra cherry flavor. Next time I may add more juice. It was hard to tell I added any to the batter.
  • About removing from the pan: To make it easier to remove the cake from the pan, run a knife along the edges before turning over onto a plate. I can’t say I perfected the method. As you can tell by my picture, my cake is still a little rough around the edges. However, I definitely think the knife trick helps.

Cooking time (duration): 15

Number of servings (yield): 6

Meal type: dessert

My rating: 5 stars:  ★★★★★ 1 review(s)

Additional Resources

If pineapple is not your thing, here are a few other skillet cake recipes using other yummy fruits.

What’s your favorite thing to make in a cast iron skillet?

4 Comments
  1. That is how I season my skillet as well with the bacon and other good greasy things. Cannot beat that flavor! I love making breakfast dishes in mine, so anything with peppers, eggs, a little meat.

    This looks just gorgeous.

    • Thanks so much! Love your idea of doing breakfast dishes in cast iron too. Now I’m hungry for eggs and sausage. :)

  2. I am completely with you on the cast iron skillet. I LOVE mine, its probably used more than anything else in my kitchen.
    And the skillet upside down cake sounds delicius!

    • Thanks! I can’t imagine cooking or baking without my cast iron skillet now.

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