01 -
Preheat your oven to 325°F (165°C). Grab a standard 12-cup muffin tin and either spray each cup with non-stick cooking spray or line with paper cupcake liners. If using liners, spray them lightly with cooking spray too - this helps with the unmolding later.
02 -
In a small bowl, stir together the 1/4 cup melted butter and brown sugar until well combined. The mixture should look like a thick caramel sauce. Spoon about 1 teaspoon of this sweet mixture into the bottom of each muffin cup. Make sure it covers the entire bottom. Now place a few small pieces of pineapple and half a cherry in each cup, pressing them gently into the brown sugar mixture. This will become the beautiful top of your upside-down cheesecakes!
03 -
In another bowl, combine the graham cracker crumbs, 3 tablespoons melted butter, and 2 tablespoons sugar. Mix until the crumbs are evenly moistened and look like wet sand. Spoon about 1 tablespoon of the crumb mixture over the pineapple layer in each muffin cup. Use the back of a spoon or the bottom of a small glass to press the crumbs down firmly over the fruit. The more compact your crust, the better it will hold together.
04 -
In a medium bowl, beat the softened cream cheese and 1/4 cup sugar with an electric mixer until smooth and creamy, about 2 minutes. Scrape down the sides of the bowl to make sure everything is well mixed. Add the egg and vanilla extract, then beat again until fully incorporated and silky smooth. Don't overmix once the egg is added - just beat until combined.
05 -
Using a spoon or a small cookie scoop, divide the cheesecake filling evenly among the muffin cups, filling each one almost to the top. The filling should come just below the rim of each cup. If you have a bit extra, distribute it evenly among all the cups.
06 -
Bake in your preheated oven for 18-22 minutes. The cheesecakes should be just set and very slightly puffed in the center, but not cracked. They'll continue to set as they cool. Don't overbake, or your cheesecakes might become dry and crack on top.
07 -
Once baked, remove the muffin tin from the oven and let the cheesecakes cool in the pan for about 10 minutes. Then, carefully run a thin knife or small offset spatula around the edges of each cheesecake to loosen it from the pan. This step is crucial for easy removal later!
08 -
Place the entire muffin tin in the refrigerator and chill for at least 2 hours, or until the cheesecakes are completely cold and firm. This chilling time is important - it helps the cheesecakes set properly and makes them easier to remove from the pan.
09 -
When you're ready to serve, place a large platter or baking sheet over the top of the muffin tin. Holding them firmly together, quickly flip everything over so the muffin tin is on top. Gently tap or shake the muffin tin to release the cheesecakes. If some stick, gently insert a knife along the edge to help release them. Once unmolded, you'll see the beautiful caramelized pineapple and cherry topping! Serve chilled, with a dollop of whipped cream if desired.