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1
Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F (175 degrees C).
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2
Spray 24 muffin cups with cooking spray.
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3
Spoon 1 teaspoon melted butter and 1/2 teaspoon bourbon into the bottom of each sprayed muffin cup.
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4
Spoon 1 tablespoon brown sugar in each muffin cup.
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5
Press a maraschino cherry into the center of the brown sugar in each muffin cup.
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6
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.
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7
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.
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8
Pour cake batter into the muffin cups, filling them to the top; do not overfill.
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9
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
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10
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.
