Old Fashioned Pineapple Upside Down Cake
Submitted by hilliard
Old fashioned pineapple upside down cake baked in a cast iron skillet with a caramelized brown sugar and butter base, pineapple rings, and pecan halves. Served warm with whipped cream.
YIELD
1 cakePREP
10 minCOOK
50 minREADY
60 minA 10-inch cast iron skillet is the only pan for this job. The heavy iron holds heat evenly, caramelizes the brown sugar and butter base perfectly, and goes straight from stovetop to oven without missing a beat. This is how pineapple upside down cake was always meant to be made.
Melt butter directly in the skillet, stir in packed light brown sugar until it dissolves into a bubbling caramel, then arrange pineapple rings in overlapping circles with pecan (or walnut) halves tucked into each center. The batter goes gently over the top. Be careful not to disturb the pineapple pattern, because whatever you see on the bottom becomes the top of the finished cake.
The reserved pineapple syrup goes right into the cake batter, adding moisture and extra fruit flavor. Beat the batter a full 2 minutes at high speed after adding the egg and syrup. That extended beating develops enough structure to support the heavy fruit topping when you flip.
Pro Tips
- Let the cake cool in the skillet for exactly 5 minutes. Less and the caramel is too hot and runny. More and it hardens and sticks.
- Loosen the edges with a spatula before flipping. One smooth, confident inversion onto a platter. Don’t hesitate.
- If a pineapple ring sticks, just peel it off the skillet and place it back on the cake. The caramel hides any imperfections.
- Serve warm with freshly whipped cream, not canned. The contrast of warm cake and cold cream is everything.
Variations
- Cherry centers: Place a maraschino cherry in the center of each pineapple ring instead of (or alongside) the nuts.
- Bourbon caramel: Add 2 tablespoons of bourbon to the butter-brown sugar mixture for a deeper, smokier caramel.
- Individual cakes: Use a muffin tin for personal-sized upside down cakes. Reduce bake time to 20-25 minutes.
Ingredients
Directions
Preheat oven to 350℉ (180℃).
Drain the pineapple slices, reserving 2 tablespoon syrup.
In a heavy cast iron frying pan (10"), melt the butter over medium heat.
Add brown sugar, stirring until the sugar is melted.
Remove from heat, and arrange 8 of the pineapple slices on the sugar mixture, overlapping the slices slightly around the edge of the pan.
Put one slice in the center.
Place the walnut or pecan halves in the center of each slice of pineapple.
Arrange around the inside edge of the skillet the remaining pineapple, cut in halves.
Put pecans or walnuts in the center.
In a medium bowl, mix the flour, sugar, baking powder, and salt.
Add shortening and milk.
Beat 2 minutes at high speed or until mixture is smooth.
Add egg and reserved 2 tablespoon of syrup. Beat 2 minutes longer. Gently pour cake batter over pineapple in skillet. Spread evenly being careful not to disarrange the pineapple. Place on center rack of oven and bake 40 to 45 minutes, or until cake springs back to light touch. After the cake is done, let the skillet stand on a wire rack 5 minutes to cool just slightly, and then loosen edges with a small spatula. Place serving platter over the cake, and turn upside down. Shake gently, and lift off skillet. Serve with 1 cup heavy cream whipped.
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