Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F (175 degrees C).
Spray 24 muffin cups with cooking spray.
Spoon 1 teaspoon melted butter and 1/2 teaspoon bourbon into the bottom of each sprayed muffin cup.
Spoon 1 tablespoon brown sugar in each muffin cup.
Press a maraschino cherry into the center of the brown sugar in each muffin cup.
Drain pineapple, saving the juice (there should be about a cup). Cut each chunk in half and surround cherry with four pieces, one on each side, covering the bottom of the muffin cup.
Mix yellow cake mix, eggs, pineapple juice, bourbon and vegetable oil in a large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
Pour cake batter into the muffin cups, filling them to the top; do not overfill.
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
Allow cupcakes to cool at least 5 minutes on a rack. Then run a small sharp knife around each cake to loosen before inverting muffin cups forcefully (with a bang!) over a large piece of waxed paper on your counter to release. Some pineapple pieces may stick to bottom, just put them back on the cakes. Serve with pineapple/cherry side up.