In a saucepan over medium heat, melt ¼ cup of butter and stir in ½ cup of brown sugar until combined.

Add the drained pineapple slices, letting them caramelize for about 5 minutes.

Arrange the caramelized pineapple slices in a single layer on the bottom of a greased 9-inch round cake pan. Place a cherry in the center of each pineapple slice for that classic look!

In a mixing bowl, combine the softened cream cheese, ½ cup granulated sugar, vanilla extract, and egg. Beat until smooth and creamy.

Set aside the cheesecake filling.

Preheat your oven to 350°F (175°C).

In a separate large bowl, whisk together the flour, baking powder, and salt.

Cream together ¾ cup of softened butter and 1 cup of granulated sugar until fluffy (about 3-5 minutes).

Beat in three eggs, one at a time, and add the vanilla.

Gradually mix in the flour mixture followed by the milk until well combined.

Pour half of the cake batter over the caramelized pineapple in the cake pan. Spread the cheesecake filling evenly on top, and then pour the remaining cake batter over the filling.

Bake for 45-50 minutes or until a toothpick comes out clean from the center.

Let it cool in the pan for about 20 minutes, then gently invert it onto a serving plate.