Prior to making this recipe, I had never had a pineapple upside-down cake. To me they’ve always seemed sort of old school—the kind of thing made by a grandmother who keeps dishes of butterscotch hard candy on her coffee table and collectible porcelain figurines on her bookshelves. Yet somehow I got it into my head that this would be the perfect dessert to take to a LOST finale party last weekend, probably because it is vaguely tropical and as ‘70s as the Dharma initiative itself.
Now that I have made a pineapple upside-down cake, I’m kind of wondering where it’s been all my life. A perfectly moist vanilla cake topped with a layer of caramelized fruit—what’s not to love? I found the recipe, appropriately enough, not on some swanky food blog or website but in my copy of The Joy of Cooking, that classic American cookbook that so much resembles an antique I find it hard to believe the recipes still work. Consider my mind changed on that one.
This recipe calls for maraschino cherries, pecan halves, or prunes as fillers for the holes in the pineapple rings. If you want to go full-out retro, then by all means use the cherries. I used blackberries because they were what I had in my fridge and maraschino cherries make me want to barf. Also because I like to think that the presence of fresh berries helps downplay the kitsch factor and brings pineapple upside down cake—in all its golden, buttery glory—into the 21st century.
Pineapple Upside-Down Cake
7 slices canned unsweetened pineapple rings
9 tablespoons butter, divided
Scant ¾ cup packed brown sugar
Maraschino cherries, pecan halves, prunes, or fresh berries
2 large eggs
8 tablespoons buttermilk, divided
½ teaspoon vanilla
1 cup flour
¾ cup sugar
¾ teaspoon baking powder
¼ teaspoon baking soda
¼ teaspoon salt
1) Drain pineapple and place on paper towel to absorb the excess juice.
2) Melt 3 tablespoons of the butter in a 9 inch cake pan (either in the oven or on the stovetop).
3) When the butter is melted, tilt the pan so that the melted butter coats all sides. The excess will settle in the bottom.
4) Sprinkle brown sugar evenly in the bottom of the pan.
5) Top with pineapple rings and “filler” of choice (if using).
6) Whisk together eggs, 2 tablespoons buttermilk, and vanilla.
7) Mix flour, sugar, baking powder, baking soda, and salt in the bowl of an electric mixer for a few seconds to combine.
8) Add 6 tablespoons softened butter and 6 tablespoons buttermilk and beat on low just until flour is moistened.
9) Increase speed to medium (or high if using a hand-held mixer) and beat for 1 ½ minutes.
10) Add egg mixture a third at a time, beating for 20 seconds and scraping the bowl after each addition.
11) Pour batter over pineapple in pan and bake at 350 for 35-40 minutes, or until a toothpick inserted into center of cake comes out clean.
12) Shake the cake lightly to loosen sides from the pan (I just went around the edges with a butter knife). Let cake cool for at least five minutes before inverting onto serving plate. Serve with loosely whipped, lightly sweetened cream.
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