1. Crafting the Creamy Cheesecake Layer:

• First things first, let’s get your oven preheated to 325°F (160°C). Grease your 9-inch springform pan and wrap the outside bottom and sides securely in heavy-duty foil (this is for our water bath later!).
• In a large bowl, grab your electric hand mixer and whip the room temperature cream cheese with the granulated sugar until it’s beautifully smooth.
• Beat in the eggs one at a time, just until each is combined. Don’t forget to scrape down the sides of the bowl!
• Gently mix in the sour cream, pineapple juice, and vanilla extract until everything is silky smooth.
• Pour this lovely batter into your prepared springform pan. Now, place this pan into a larger roasting dish.
• Reduce your oven temperature to 300°F (150°C). Carefully place the roasting dish (with the cheesecake pan inside) into the oven.
• Pour hot water into the roasting pan, letting it come about halfway up the sides of your cheesecake pan. This water bath is the secret to a crack-free, perfectly moist cheesecake!
• Bake for 45 minutes. Then, turn off the oven heat and let the cheesecake sit in the warm oven for another 20 minutes to set up.
• Take the cheesecake out of the oven and lift it from the water bath. Let it cool completely on a wire rack to room temperature. Once cooled, cover it with plastic wrap and pop it into the fridge to chill for at least 8 hours – overnight is even better for the ultimate texture!

2. Preparing the Pineapple-Cherry Topping (for the Cakes):

• Grab two 9-inch round cake pans. Divide the 1/2 cup of melted unsalted butter evenly between them.
• Sprinkle 1/2 cup of packed light brown sugar into each pan, right over the butter.
• Now for the fun part! Arrange your pineapple slices and maraschino cherries in a pretty pattern at the bottom of each pan. Set these aside while we make the cake batter.

3. Mixing the Pineapple Cake Batter:

• Preheat your oven to 350°F (175°C).
• In a large bowl, whisk together your sifted all-purpose flour, baking powder, baking soda, and salt.
• In a separate medium-sized bowl, whisk the 1/2 cup melted unsalted butter with the 3/4 cup light brown sugar and 1/4 cup granulated sugar until smooth.
• To this sweet mixture, whisk in the egg, sour cream, milk, pineapple juice, and vanilla extract until everything is just combined.
• Time to bring it all together! Add the wet ingredients to the dry ingredients and stir gently until just combined. Try not to overmix – we want a tender cake! Make sure there are no dry floury bits left.
• Carefully divide this batter evenly between your two cake pans with the pineapple topping, smoothing the top gently so you don’t disturb your beautiful fruit arrangement.
• Bake for 25-30 minutes. The cakes are ready when they’re golden brown and a toothpick inserted into the center comes out clean.
• Let the cakes cool in their pans on a wire rack for about 10 minutes before you invert them.

4. Assembling Your Masterpiece:

• Carefully invert one cake layer onto a cutting board or flat surface (this will be your middle layer). Invert the second cake layer onto your final serving plate (this is your base).
• Gently release your chilled cheesecake from its springform pan. You might need a thin offset spatula to help lift it from the pan bottom.
• Carefully place the cheesecake layer on top of the cake layer that’s on your serving plate.
• Finally, gently place the second cake layer (pineapple side up!) on top of the cheesecake.
• Voilà! You can serve your Pineapple Upside Down Cheesecake immediately, or pop it back in the fridge to keep it cool until you’re ready to dazzle your guests.