It is funny how we are captured by tastes from our past. They seem to never leave us, even when we push them aside.
Pineapple upside down cake is one of those ghosts from my past. Long past.
In my test kitchen days, pineapple upside down cake was the popular rage. I saw the buttery rich cake often at potlucks and church dinners and it was always a hit. In the test kitchen, it was a great way to test an electric skillet to see if the heat was even so we made them frequently. It was a favorite of my parents so I remember special dinners with the occasional pineapple upside down cake. The thing is, it was always made with canned pineapple and a cake mix. It also always had a few of those bright Maraschino cherries scatted about. (Not that I am against cherries, mind you, but I don’t know if they added a lot to the classic cake.)
I hadn’t thought much about that cake for years. I could not tell you the last time I had a piece.
Then I was reading One Big Table by Molly O’Neill, and there it was. A pineapple upside down cake made from fresh pineapple. Without cherries! Suddenly, I was obsessed and had to make a version of it. Now I keep making it.
Homey, buttery, sweet and gooey. But the fresh pineapple shines through!
Pineapple Upside Down Cake
1/2 fresh pineapple
14 tablespoons unsalted butter, softened, divided
1 cup light brown sugar
3 tablespoons orange or pineapple juice
1 cup plus 6 tablespoons all-purpose flour
1 teaspoon baking powder
1/4 teaspoon salt
1 cup sugar
2 large eggs
2 teaspoons pure vanilla extract
1 cup milk
Preheat the oven to 350⁰F. Lightly oil a 10-inch cast iron skillet about 2 inches deep.
Peel the pineapple, then cut the pineapple half in half lengthwise. You will have two long spears. Cut out the core. Cut the spears crosswise into slices about 1/2 – inch thick. You will have about 16 to 20 slices. Set aside. (Use the remaining half of the pineapple in other recipes or slice and just enjoy!)
Heat the skillet over medium heat. Cut 8 tablespoons butter into 1-tablespoon slices and place in the skillet to melt. Once the butter is melted, sprinkle with brown sugar and cook, stirring frequently for 2 to 3 minutes or until the sugar is melted. Stir in the juice and cook, stirring, for 1 minute. The syrup will be boiling. Remove from the heat.
Carefully arrange the pineapple slices in the syrup in the skillet.
In a small bowl, whisk together flour, baking powder and salt; set aside.
In a medium bowl, using an electric mixer at medium speed, beat together the remaining 6 tablespoons of butter and the sugar, beating until light and fluffy. Beat in eggs, one at a time, beating well after each. Beat in vanilla. Beat in the flour mixture, alternately with the milk, making three additions of flour and two of milk and blending until moistened.
Pour the batter over the pineapple in the skillet.
Carefully place the skillet in the oven. Bake, uncovered, for 35 to 40 minutes or until a toothpick inserted into the cake comes out clean. Carefully remove from the oven and allow to stand 15 minutes. Cut into wedges and serve from the skillet.
Makes 6 to 8 servings.
Tip
It is much safer to serve the pineapple upside down cake from the skillet. It takes a lot of strength and is quite dangerous to turn it out. The syrup is boiling hot and could make a nasty burn. It is easy to turn the slices over on the plate you serve them.
*Inspired by Sylvie Rowland’s Pineapple Upside Down Cake in One Big Table: A Portrait of American Cooking, by Molly O’Neill.
You are right, for me at least I have very definitive memories tied to certain foods. My grandma made the most lovely pineapple upside down cake in a cast iron skillet. It was always a highly coveted position to be asked by her to help make it. I was really high strung, hyper, and didn’t always follow directions, so my older sister got asked to help more often than me. I’ve never had a pineapple upsidedown cake with fresh pineapple, my interest is certainly piqued!