I have never made upside down anything before. I actually didn't really understand what "upside down" part of it was til quite recently. Basically it's caramelizing fruit in a skillet then pouring cake batter on top. Then flip it and tada! A fancy looking cake.
History digression: Pineapple upside down cake (aka pineapple glacé and pineapple skillet cake) was thought to have first appeared in the 1920s. Coincidentally, that's when canned pineapple became huge, thanks to Jim Dole's Hawaiian Pineapple Company (yep the same Dole canned fruits you see today). He canned 95% of the crop which led to a huge expansion of the canned pineapple market (source).
Fun fact: The term "maraschino cherries" refers to the method of preservation. It's kinda scary how they make them - first bleach in a brine solution with sulfur dioxide and calcium chloride then soak in sugar and red food coloring/FD&C Red 40 (yikes!) And I always thought maraschino was a just type of cherry like Bing or Ranier...
I double batched the original recipe from Gourmet so it serves a lot of people, around 16-18. I cut the sugar and the topping by half (the original had way too much butter/sugar topping for me) and used a springform pan lined with foil for easier release rather than a skillet. It's a fairly dense cake, like pound cake, and the pineapple and orange combo was prefect. Alas I didn't have any rum.
This was addictingly good...I ate a lot...probably more than the first year med students whom I baked it baked for.
1 can pineapple rings in pineapple juice
1/2 stick (1/4 cup) unsalted butter
1/2 cup light brown sugar
3 cups all-purpose flour
1 1/3 tablepoons baking powder
1/2 teaspoon salt
1 1/2 sticks (3/4 cup) unsalted butter, softened
1 cup granulated sugar
4 large eggs
1 tablespoon vanilla extract
1 tablespoon orange or rum extract
1 orange zested
1 cup unsweetened pineapple juice
1 springform pan, lined with foil (The foil prevents leaking while baking and makes it easier to invert the cake)
Preheat oven to 350°F.
Melt butter in skillet. Add sugar and simmer over moderate heat, stirring, until browned (~5 min). Pour caramelized sugar into a springform pan lined with foil. Arrange pineapple rings on top of sugar mixture.
Sift together flour, baking powder, and salt in one bowl.
Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, 1 at a time, beating well after each addition. Beat in extracts, zest, and rum.
Add half of flour mixture and stir until just blended. Add pineapple juice, then stir in remaining flour mixture, until just blended (batter may appear slightly curdled).
Pour batter carefully over pineapple topping. Bake cake until golden and a tester comes out clean, about 45 minutes. Let cool. Remove the springform sides, invert cake onto plate, and peel off the foil. Serve cake just warm or at room temperature.