Preheat & Prep: Preheat your oven to 325°F (160°C). Line the bottom of a 9-inch springform pan with parchment paper and grease the sides of the pan with a little butter or cooking spray to prevent sticking.
Make the Crust: In a medium bowl, mix together 1½ cups of graham cracker crumbs, ¼ cup of brown sugar, and 6 tablespoons of melted butter. Stir until the mixture is fully combined and resembles wet sand. Press the mixture firmly into the bottom of the prepared springform pan to form the crust. Bake the crust in the preheated oven for 10 minutes, then remove it and let it cool completely while you prepare the filling.
Make the Cheesecake Filling: In a large bowl, beat the 24 oz of softened cream cheese until smooth and creamy. Add ¾ cup of granulated sugar and mix until fully combined. Add the 3 eggs one at a time, mixing on low speed after each addition to avoid over-beating. Stir in 1 teaspoon of vanilla extract, ½ cup of sour cream, and ½ cup of pineapple juice. Continue mixing until the batter is smooth and well-combined. Pour the cheesecake filling over the cooled graham crust, smoothing the top with a spatula.
Bake the Cheesecake: To prevent cracks in the cheesecake, wrap the bottom of the springform pan in foil and place the pan in a large roasting pan. Pour hot water into the roasting pan until it reaches about halfway up the sides of the springform pan, creating a water bath. Bake the cheesecake in the preheated oven for 50–60 minutes, or until the center is just set but slightly wobbly when gently shaken. Turn off the oven, crack the oven door slightly, and let the cheesecake sit in the oven for an additional hour. This gentle cooling process helps prevent cracks. After an hour, remove the cheesecake from the water bath and allow it to cool to room temperature. Once cooled, refrigerate the cheesecake for at least 4 hours or overnight for the best results.
Make the Pineapple Topping: While the cheesecake is cooling, prepare the caramelized pineapple topping. In a skillet, melt 1 tablespoon of butter over medium heat. Add 2 cups of fresh pineapple chunks, 2 tablespoons of brown sugar, and 1 tablespoon of pineapple juice. Cook the mixture for 5–7 minutes, stirring occasionally, until the pineapple becomes golden brown and caramelized. Remove from heat and let it cool completely.
Assemble & Serve: Once the cheesecake is fully chilled, carefully remove it from the springform pan and transfer it to a serving platter. Top the chilled cheesecake with the cooled caramelized pineapple. Slice the cheesecake into wedges, serve, and enjoy the tropical flavor explosion!
