Preheat the oven to 325 degrees F (165 degrees C).
Mix 2 tablespoons butter and brown sugar together in a 9-inch round cake pan until blended; spread mixture to evenly cover the bottom of the pan. Top with pineapple slices, then place one cherry into the center of each slice.
Mix graham cracker crumbs, 3 tablespoons white sugar, and remaining 3 tablespoons melted butter together in a small bowl until well combined. Press mixture over pineapple slices.
Beat cream cheese and 3/4 cup white sugar in a bowl until blended. Add sour cream and vanilla; mix well. Add eggs, one at a time, mixing on low speed after each addition until blended. Pour batter into the cake pan.
Bake in the preheated oven until the center is almost set, 55 minutes to 1 hour. Remove from the oven.
Run a knife around the inside edge of the pan to loosen. Allow to cool completely, about 30 minutes. Invert onto a serving plate and refrigerate for at least 3 hours before serving.
Nutritional Facts
Per 8 servings
Calories: 599
Carbohydrate: 45g
Fat: 44g
Fiber: 1g
Protein: 9g
Sugar: 37g
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