Prepare the Pineapple Layer:
Preheat the oven to 350°F (175°C). Grease a 9-inch springform pan and line the bottom with parchment paper.
Pour the melted butter into the pan and sprinkle the brown sugar evenly over it. Arrange the pineapple slices in a single layer on top of the sugar, placing cherries in the centers of the slices.
Make the Cheesecake Layer:
In a large bowl, beat the cream cheese and sugar until smooth. Add the eggs, one at a time, mixing after each addition. Stir in the vanilla, sour cream, and heavy cream until well combined.
Pour the cheesecake batter over the pineapple layer and smooth the top with a spatula. Bake for 45–50 minutes, or until the center is set. Let cool completely.
Prepare the Cake Layer:
In a medium bowl, cream together the butter and sugar until light and fluffy. Beat in the eggs, one at a time, followed by the vanilla extract.
In another bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, alternating with the milk, starting and ending with the dry ingredients.
Pour the cake batter over the cooled cheesecake layer.
Bake the Combined Cake:
Bake for an additional 25–30 minutes, or until a toothpick inserted into the cake layer comes out clean. Allow the cake to cool in the pan for 15 minutes before running a knife around the edges to loosen.
Invert and Serve:
Carefully invert the cake onto a serving platter. Remove the springform pan and parchment paper. Chill in the refrigerator for at least 2 hours before serving.
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