Preheat oven to 350 degrees Fahrenheit and lightly spray a 12-count cupcake tin with non-stick baking spray.
Evenly divide the 6 tablespoons melted butter into the bottom of each cupcake well. sprinkle the bottom of each cup with 1 tablespoon of the ¾ cup brown sugar.
Lay 4 of the 1 (20-ounce) can +1 (8-ounce) can pineapple chunks in pineapple juice, in a flower pattern over butter and brown sugar in each cup. Press one of the 12 maraschino cherries into the center of each "flower". Set aside.
Cupcakes
Using a hand mixer, whisk the ½ cup softened unsalted butter and ¾ cup granulated sugar in a medium-sized bowl until creamy and well combined.
Add the 2 eggs, whisking one at a time until combined. Stir in the 1 teaspoon vanilla extract.
In a separate bowl, whisk together 1 ½ cups all-purpose flour, 1 ½ teaspoons baking powder, and ¼ teaspoon salt.
Alternate adding flour mixture and ½ cup buttermilk to the butter mixture, starting and ending with flour, using a spatula and mixing until just combined after each addition
Evenly divide the cupcake batter into the prepared pan. The batter will be thick, so use a spoon to spread it evenly into each cupcake well. Fill each cupcake well to the top.
Bake for 22-25 minutes. Remove, allow to cool for 5 minutes, and then place a wire cooling rack over the cupcake tin, covering each cupcake.
Carefully, use oven mitts as the tin will be very hot, keep the cooling rack pressed against the tin flip it over. Lift the muffin tin off the cooling rack and the cupcakes should release easily.
Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!
Notes
*This recipe can easily be doubled for 24 cupcakes