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Spray a standard 9-inch cake pan with non-stick cooking spray.
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In a small saucepan, melt 4 tbsp butter and 1/2 cup brown sugar over low heat until fully dissolved and smooth. Pour into the cake pan, tilting to cover the bottom evenly.
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Pat drained pineapple slices and cherry halves dry with paper towels. Arrange the fruit decoratively over the caramel layer (if using cherry halves, place them cut-side up).
Make the Cake Batter:
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In a large bowl, whisk 5 tbsp melted butter with 2/3 cup granulated sugar.
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Add the eggs one at a time, whisking well.
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Stir in buttermilk, baking powder, baking soda, salt, and vanilla extract.
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Fold in the flour until just combined (do not overmix).
Bake & Invert:
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Gently spread the batter evenly over the fruit layer.
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Bake at 350°F (175°C) for 30 minutes or until a toothpick inserted in the center comes out clean.
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Let cool in the pan for 1 minute. Place a rimless baking sheet upside down over the pan, and carefully invert the cake onto it. Allow to cool completely.
Final Assembly
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Remove the chilled cheesecake from the fridge and release the outer ring of the springform pan.
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Place the cheesecake (on its springform base) onto your serving platter.
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Using a large spatula, carefully slide the cooled Pineapple Upside-Down Cake off the rimless baking sheet and slide it directly onto the top of the cheesecake layer.
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Slice and serve immediately. Optionally, top with warm caramel drizzle and extra maraschino cherries!
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