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

Drain the pineapple slices and reserve the syrup for later use if desired.

In a skillet over medium heat, melt the butter and brown sugar together until bubbling and smooth.

Arrange the pineapple slices in the bottom of the prepared pan. Place maraschino cherries in the centers and any open spaces.

Pour the brown sugar mixture evenly over the pineapple and cherries.

In a mixing bowl, combine graham cracker crumbs, sugar, and melted butter until the mixture resembles wet sand.

Press the crust mixture evenly over the pineapple layer.

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

Add vanilla extract and flour, mixing until incorporated.

Add eggs one at a time, beating gently after each addition.

Pour the cheesecake mixture over the crust and smooth the surface.

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

Remove from the oven and allow the cheesecake to cool completely.

Refrigerate for at least 4 hours or overnight for best results.

Carefully invert onto a serving plate before slicing.

Drizzle with reserved pineapple syrup if desired and serve.