Preheat your oven to 325°F (163°C) and grease a 9-inch springform pan. Sprinkle ½ cup of brown sugar at the bottom, arrange the pineapple rings on top, and place a maraschino cherry in the center of each ring. Drizzle melted butter over the layer.

In a mixing bowl, combine 1 ½ cups of graham cracker crumbs with ½ cup of melted unsalted butter. Press this mixture over the pineapple layer in the springform pan and freeze for 10 to 15 minutes.

In a large bowl, beat 16 ounces of softened cream cheese with ½ cup of granulated sugar until smooth. Gradually add in three eggs, mixing on low. Incorporate ¾ cup of sour cream and 1 teaspoon of vanilla extract until blended.

Pour the cheesecake filling over the chilled crust and pineapple layer, smoothing the top.

Place the springform pan into a larger baking dish and pour hot water into the outer dish until it reaches halfway up the sides. Bake for 60–70 minutes, or until the center is set but slightly jiggly.

Turn off the oven and leave the cheesecake inside with the door slightly ajar for an hour to cool.

Allow the cheesecake to cool at room temperature for 30 minutes before refrigerating for at least 4 hours or overnight.

Run a knife around the edges to loosen and release the sides of the springform pan. Invert onto a serving plate and slice to enjoy.