I'm not sure if this is a contested fact, but the Pineapple Upside-Down cake just screams "American," which is strange because pineapples aren't a fruit associated with mainland America. I'll have to check what event in the sixties prompted thousands of homemakers to take notice of this treat, with its unfrosted face, gleaming with slick buttered pineapples and sometimes dotted with cherries. I am not even sure what about pineapple lends itself to adorning a humble butter cake instead of the less-popular but still delicious alternatives of stone fruits, cranberries, and apples. Maybe it's because it pairs with brown sugar so remarkably well that they can cut through plain cake and make no apologies for not having frosting. Whatever the reason, it perpetuates its existence through our cravings-- which is what happened with my mom when she saw it on display and wanted to buy one; I told her not to bother as it is much cheaper (and often more delicious) to make at home. (Recipe follows)
The problem was, many recipes call for fresh pineapple, which is really a bother as its ripeness is never guaranteed, and there's the business of peeling, coring, and slicing it, which are great skills but I'm not really up to at this time. Unfortunately, I miscalculated the amount of pineapple tidbits I'd need and opened a 450g can, which left a lot of gaps on top-- I wanted there to be no space so the surface would open up and be all porcupine-y. Oh well, a lesson for next time. Alternatively, you can use sliced pineapple and make the classic "target" patterns on top, or arrange them concentrically to form a giant flower. The choice is yours!
At least a few hours before baking, place the pineapple tidbits between thicknesses of paper towels and weigh down in the refrigerator. Alternatively, you could pat the pineapple very dry with paper towels. Stir together the melted butter and brown sugar, then spread on the bottom of a 9-inch cake pan (that is at least 2 inches tall) that has been greased on the sides. Arrange the pineapple on the sugar mixture.
Ingredient preparations: in a triple-sifter or a strainer, add the flour, baking powder, salt, and cinnamon, and sift over a bowl or some waxed paper. Add the vanilla extract to the milk and stir to combine.
Place a rack in the center of the oven and preheat the oven to 350°F (175°C). In a large bowl, cream the butter and sugar together using an electric mixer on high speed until light and fluffy (you can do this by hand but it will take a while). Add the eggs one at a time, beating on high speed after each until well-combined. Sprinkle 1/3 of the flour mixture and fold in. Add half the milk and beat until just combined. Repeat with another third of the flour and the rest of the milk, then fold in the last of the flour until just combined. Pour into the pan and spread evenly. Bake for 45 to 55 minutes, until a round toothpick inserted into the center comes out with only a few fine moist crumbs. Cool the cake in its pan on a rack for 15 minutes, then run a thin knife around the edge and lay the serving plate on top. Flip the set-up in a quick motion and cool the cake completely (or you may serve it slightly warm, with ice cream).