Preheat your oven to 325°F (160°C). Grease a springform pan thoroughly.

Drain the pineapple slices and reserve the syrup for later.

In a skillet over medium heat, combine melted butter and brown sugar. Stir until bubbling and smooth.

Arrange pineapple slices and maraschino cherries in the bottom of the prepared pan. Pour the brown sugar mixture evenly over the fruit.

In a medium bowl, combine graham cracker crumbs, sugar, and melted butter until crumbly.

Press the crust mixture gently over the pineapple layer to create an even base.

In a large bowl, beat softened cream cheese and sugar until creamy and smooth.

Add vanilla extract and flour, mixing until fully combined.

Add eggs one at a time, mixing well after each addition.

Pour the cheesecake filling over the crust and smooth the top with a spatula.

Bake the Pineapple Upside Down Cheesecake Cake for 50–60 minutes or until the center is mostly set.

Remove from the oven and cool completely at room temperature.

Refrigerate for at least 4 hours before carefully inverting onto a serving plate.

Drizzle reserved pineapple syrup over the top if desired. Slice and serve chilled.