Preheat the oven to 350°F (325°F for a dark or nonstick pan).
Place 1/4 cup butter in a 9x13-inch baking pan and place the pan in the oven until the butter is melted.
Remove the pan from the oven and sprinkle 1 cup packed brown sugar evenly over the melted butter.
Arrange the drained 20-ounce can of pineapple slices over the brown sugar. Place 1 drained maraschino cherry in the center of each pineapple slice, then arrange the remaining drained cherries around the pineapple slices, pressing them gently into the brown sugar.
Pour the reserved pineapple juice into a measuring cup and add enough water to equal 1 cup of liquid.
Prepare 1 box yellow cake mix according to the package directions, using the 1 cup pineapple juice mixture in place of the water and adding the amount of vegetable oil and eggs called for on the cake mix box.
Pour the prepared cake batter evenly over the pineapple and cherry layer.
Prepare 1 box yellow cake mix according to the package directions, using the 1 cup pineapple juice mixture in place of the water and adding the amount of vegetable oil and eggs called for on the cake mix box.
Bake for 40 to 50 minutes, or until a toothpick inserted into the center comes out clean.
Immediately run a knife around the edge of the pan to loosen the cake.
Place a heatproof serving platter upside down over the baking pan. Carefully invert the pan and platter together.
Leave the pan on top of the cake for 5 minutes to allow the brown sugar topping to drizzle over the cake, then carefully remove the pan.
Cool the cake for 30 minutes before serving. Enjoy warm or at room temperature.
Store any leftovers covered in the refrigerator.