Prepare the Crust: In a medium bowl, mix the graham cracker crumbs, melted butter, and granulated sugar until well combined. Press this mixture firmly into the bottoms of your mini cheesecake molds or cupcake liners.
Cook the Pineapple: In a skillet over medium heat, melt the brown sugar, stirring until it begins to bubble. Add the drained pineapple slices and cook for 3-5 minutes per side, until they are nicely caramelized. Remove the skillet from the heat and let the pineapple cool slightly.
Make the Filling: In a large bowl, using an electric mixer, beat the softened cream cheese and powdered sugar together until smooth and creamy. Gently fold in the whipped cream until the mixture is light and well combined.
Assemble the Cheesecakes: Place one caramelized pineapple slice at the bottom of each prepared mold or liner.For surrounding the cheesecake (optional): You can cut additional caramelized pineapple slices into smaller pieces and arrange them around the inside edges of the molds/liners before adding the filling. This will create a pineapple border when unmolded or when eating. Spoon the cream cheese filling evenly over the pineapple (and around the edges, if you chose to line them), smoothing the top. Chill: Refrigerate the mini cheesecakes for at least 4 hours, or preferably overnight, until they are firm and set.
Serve: If using molds, you can carefully invert them before serving (though with the mini size, enjoying them as is is perfectly fine!). Garnish with a maraschino cherry, if desired.