Homemade Pineapple Upside down Cheesecake


For the topping:

  • 1/4 cup unsalted butter
  • 3/4 cup packed brown sugar
  • 1 can (20 oz) pineapple slices in juice, drained and juice reserved
  • Maraschino cherries, for decoration

For the crust:

  • 1 1/2 cups graham cracker crumbs
  • 1/4 cup granulated sugar
  • 1/2 cup unsalted butter, melted

For the cheesecake:

  • 3 packages (8 oz each) cream cheese, softened
  • 1 cup granulated sugar
  • 3 large eggs
  • 1 tablespoon vanilla extract
  • 1/4 cup reserved pineapple juice


  1. Preheat the oven to 325°F (160°C).
  2. In a 9-inch springform pan, melt the butter over low heat. Add the brown sugar and stir until the mixture is smooth and bubbly.
  3. Arrange the pineapple slices on top of the brown sugar mixture, and place a maraschino cherry in the center of each slice.
  4. In a medium mixing bowl, combine the graham cracker crumbs, granulated sugar, and melted butter. Mix until the mixture is moistened and crumbly.
  5. Press the graham cracker mixture into the bottom of the springform pan, on top of the pineapple and brown sugar mixture.
  6. In a large mixing bowl, beat the cream cheese and granulated sugar until creamy and smooth. Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract and reserved pineapple juice.
  7. Pour the cheesecake mixture into the springform pan, on top of the graham cracker crust.
  8. Bake the cheesecake in the preheated oven for 1 hour or until the center is almost set.
  9. Remove the cheesecake from the oven and let it cool to room temperature.
  10. Once the cheesecake has cooled, cover it and refrigerate it for at least 4 hours, or until completely chilled.
  11. When ready to serve, run a knife around the edges of the cheesecake to loosen it from the pan. Carefully remove the sides of the pan and invert the cheesecake onto a serving plate.
  12. Slice and serve the homemade pineapple upside-down cheesecake, and enjoy!

Note: You can also use fresh pineapple slices instead of canned if desired. If using fresh, be sure to remove the core and slice the pineapple thinly.

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