Preheat your oven to 325°F (163°C). Grease a 9-inch springform pan with non-stick spray or butter and sprinkle an even layer of brown sugar over the bottom.

Arrange pineapple rings on top of the brown sugar layer in the springform pan, placing a maraschino cherry in the center of each pineapple ring.

Combine graham cracker crumbs with melted unsalted butter until mixed. Press the mixture into the bottom of the springform pan over the pineapple layer. Freeze for 10-15 minutes.

Beat softened cream cheese and granulated sugar until smooth and creamy. Scrape down the sides for an even mixture.

Gradually add eggs, one at a time, mixing slowly on low speed. Avoid over-mixing to prevent cracks.

Stir in sour cream and vanilla extract until well-combined. The filling should be creamy and luscious.

Pour the cheesecake mixture over the crust in the springform pan and smooth the top with a spatula.

Place the springform pan into a larger dish and fill it with hot water halfway up the sides. Bake for 60-70 minutes.

Turn off the oven, crack the door, and let the cheesecake cool slowly in the oven for about 1 hour.

Chill the cheesecake in the refrigerator for at least 4 hours or ideally overnight before serving.

Run a knife around the edge of the cheesecake to loosen it, release the springform, and invert onto a serving plate.