

Don’t expect a big, bouncy sponge. The pineapple upside down is quite a flat cake. But what you can expect is a beautifully moist cake with a heavenly syrup.
I wrote about the history of the pineapple here, and how it was nicknamed King Pine by Charles II. But what about the history of the pineapple upside-down cake?
My initial guess was it originated in America, and it kind of was. This website makes the point that baking fruit and sugar under a cake layer was around in Europe for hundreds of years before (think tarte Tatin).
But the idea of using canned pineapple in the topping stems from the US in the mid 1920s. Canning technology had considerably improved by then, so sliced pineapple was more readily available, and more acceptable. There were some recipes around in the early 1920s. But the popularity exploded after the Hawaiian Pineapple Company sponsored a contest for canned pineapple recipes in 1925. It was flooded with upside-down cakes, presumably a lot of canny home cooks (see what I did there?). The pineapple upside-down cake subsequently won, and a lot of marketing surrounded the contest. At the time, it was considered quite fancy and elegant, but by the 1950s was thought of as more homey.
What I love is that it’s still terrific.
This recipe is a little different from other pineapple upside-down cake recipes I see, in that it contains buttermilk, but it was given to me many, many years ago by a lovely American. So that 100% counts.
“The sight our foolish heart inflames,
-william cowper (1731-1800), extract from The Pine-Apple And the Bee, Poem in Public domain
We long for pine-apples in frames;
With hopeless wish one looks and lingers;
One breaks the glass, and cuts his fingers;
But they whom truth and wisdom lead
Can gather honey from a weed.”

Pineapple Upside Down Cake
Ingredients
Topping
- 60 g unsalted butter (¼ cup)
- ½ cup brown sugar, moderately packed
- 430 g tin pineapple rings (a lot of people say get the rings in juice because they add the juice to the batter, but I think in syrup is ok too)
- optional – maraschino cherries, pecan halves, or dried cranberries as seen in photos above
Batter
- 2 eggs
- ⅓ cup vegetable oil
- 1 cup sugar – white or brown or a combination
- 2 tsp vanilla extract
- ½ cup buttermilk
- 1½ cups plain flour
- ½ tsp salt
- 2 tsp baking powder
Instructions
- Preheat oven to 180℃/350℉.
Topping
- Melt butter in saucepan over low heat, add brown sugar and stir until dissolved.
- Pour topping into 23cm/10" cake pan.
- Place pineapple rings in the topping ensuring sides touch. Either use whole rings, or a single whole in the centre, surrounded by half rings. Add cherries and nuts if using.
Batter
- Sift flour, salt and baking powder together.
- Beat eggs until light. Add vegetable oil. Add in sugar, milk and vanilla.
- Add in the flour mixture and beat on medium for a few minutes.
- Spoon batter over topping. Bake for 30 minutes or until skewer is clean.
- After taking cake out of the oven, invert onto a plate. Leave the cake in the pan upside down for five minutes to make sure all the topping drops out of it before removing.
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