Heat the oven to 350ยบ. Place the butter and milk for the batter in a small saucepan over medium heat. Warm the mixture, stirring occasionally, until the butter melts, then transfer the mixture to a small bowl to cool.
Meanwhile, prepare the pine-apple topping. Into each cup of a 12-cup muffin pan, add 1/2 tablespoon of unmelted butter, then evenly sprinkle 1 tablespoon of brown sugar over the bottom. Place the pan in the oven until the butter melts, about 3 minutes.
Halve each maraschino cherry, then cut the pineapple rings into quarters. Place a cherry half, sliced side up, in the center of each cup and lay a pineapple quarter on each side. Press the fruit gently down into the butter-sugar mixture, then set the prepared pan aside.
Finish making the batter. In a medium-size bowl, combine the flour, baking powder, and salt, and stir the ingredients with a fork until they're evenly blended. In a large bowl, whisk together the eggs, sugar, and vanilla extract until smooth. Add the flour mixture to the egg mixture and stir until the flour is fully incorporated. Add the milk-butter mixture and stir well to combine the ingredients into a smooth batter.
Pour the batter into the muffin pan, dividing it evenly among all the cups. Bake the cupcakes until they're lightly browned, dry around the edges, and pulling away from the pan a little, about 25 minutes.
Transfer the pan to a rack to cool for 5 minutes. Use a butter knife to carefully loosen each cupcake from the edges and bottom of the pan, then place a cookie sheet over the top. Invert the pan, turning the cupcakes out onto the cookie sheet, then transfer them back to the rack to cool completely. Serve the cupcakes at room temperature. Makes 12 cupcakes.
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