Easy as 1-2-3… 4! Pineapple Upside Down Cake

If man could only have one pan, it would probably have to be an iron skillet. You can fry, bake, sear and roast with these workhorses of the kitchen. Baking, as in cornbread, is most often thought of when using these pans for non-frying purposes, but there is a class of cakes that take the cake when it comes to iron skillet cooking, and the Pineapple Upside Down Cake is one of them.  


I actually made this cake for Mama and Mimi’s birthday. They share the same birthday and don’t always want the same cake for their special day, but, this one is a great neutral for our family – everyone likes it! Mimi makes hers in an iron skillet as did Mema, her mother. This is one of those desserts with one arm reaching back to the “Ol’ South” via an iron skillet and another broadly stepping into the mid-twentieth century with the Baby Boomers and the craze for canned fruit! It seems that by the 1980’s and 90’s fresh fruit was hard to come by in Suburbia, USA, but thankfully those days are waning and fresh, seasonal produce is here to stay!

Yet, one canned fruit this Farmer relies heavily on is canned pineapple. It tastes great, bakes marvelously, and is consistently good throughout the year. I’ve tried this recipe with freshly cored pineapple (I can’t core it prettily, so I rely on the grocer) but there is still some toughness that the fresh pineapple retains. The canned has marinated in juice for a while so it must be good! Plus, it is in perfect rings which makes a lovely presentation. As for the cherries, fresh or canned work just fine… if you like a bar cherry, go with canned. If you like a fresh one, then go with those… comes down to personal preference my dears, personal preference.

As to how this cake is easy as 1-2-3-4 comes from the cake itself. An old standby in the cake world, the 1-2-3-4 Cake derives its name from the amounts in its ingredients list. If you memorize this cake or have it on hand, you’ll always have a super cake to bake for your friends and family. This cake is cake at is simplest and its best. I don’t know how to describe it other than as a cake; that’s what it is! If you are boxed cake mix kind of folks, then it’s somewhat akin to a yellow cake mix; and, since this cake is so deliciously neutral, it is the perfect candidate for Pineapple Upside Down Cake.

The next trick to the trade that makes this Farmer’s Pineapple Upside Down Cake so yummy is the “frying” of the pineapple. Get your griddle hot, your butter melted and place the rings in the pan. A generous sprinkling of brown sugar and a cherry in the center of each ring makes the pineapple brown and crisp up a bit, thus creating a crunchy, tangy, ab fab layer to the top of your cake. The molasses in the brown sugar (that’s what makes it brown, ps) and the sugar caramelize…need I go on?

Once the pineapple has browned and is showing some golden goodness, remove it from the heat and pour your batter over the “fried” pineapple and bake at 350 until a toothpick inserted in the center comes out clean – about 20-25 minutes. Allow the cake to cool for about 10 minutes and then skillfully flip your upside down cake right side up! Slice and enjoy! A scoop of vanilla bean ice cream never hurts! Easy as 1-2-3-4 from this Farmer’s kitchen to yours!

Pineapple Upside Down Cake and 1-2-3-4 Cake
1 can of cored pineapple rings, about 8 rings
8 cherries
½ a cup of light brown sugar
½ a stick of butter

  • Melt butter in an iron skillet on medium low heat and “fry” pineapple in butter. Sprinkle pineapple with brown sugar. Add a cherry to the center of each pineapple ring. Lightly lift pineapple to check for browning and remove from heat once edges are browned and sugar dissolved…about 5 minutes max.
1 cup of whole milk
1 teaspoon of vanilla
2 sticks of unsalted butter
2 cups of sugar
3 cups of sifted cake flour (Swan’s  Down) *** NOTE: the back of the Swan’s Down box has this recipe!
3 teaspoons of baking powder
4 eggs
½ teaspoon of salt

  • Preheat oven to 350. Butter and lightly flour three 9”layer cake pans. Sift cake flour then lightly spoon 3 cups of cake flour into measuring cup.
  • Cream butter in a large bowl. Gradually add sugar, creaming until light and fluffy.
  • Sift the already sifted cake flour with baking powder and salt. Add eggs one at a time to creamed mixture, beating well after each addition.
  • Add flour mixture alternately with milk and vanilla, blending after each addition until smooth. Don’t overbeat, for this makes a dry cake. Pour into prepared cake pans. For the Pineapple Upside Down Cake, pour batter into iron skillet on top of pineapple and sugar mixture to just about halfway up the skillet. Bake remaining cake in separate pans or make additional Pineapple Upside Down Cakes!
  • Bake for 20-25 minutes or until toothpick inserted in the center comes out clean. Cool in the pans or skillet for 10 minutes and then remove cakes.
  • Flip the cake from the iron skillet onto a cake plate or wax paper. Serve warm with ice cream! Enjoy!