Step 1: Prepare the cheesecake filling. In a large mixing bowl, beat the softened cream cheese, powdered sugar, and vanilla extract with an electric mixer until completely smooth and creamy.
Step 2: In a separate, chilled bowl, whip the cold heavy cream to stiff peaks. Be careful not to over-whip, which can make it grainy.
Step 3: Gently fold the whipped cream into the cream cheese mixture using a spatula until just combined and uniform. Avoid overmixing to maintain the light, airy texture.
Step 4: Assemble the cups. Divide about half of the crumbled brownies and layer them evenly at the bottom of 6-8 individual dessert cups or jars.
Step 5: Spoon or pipe a generous layer of the cheesecake filling over the brownie crumbs. If using a piping bag, this will create cleaner layers.
Step 6: Drizzle a small amount of chocolate ganache and caramel sauce over the cheesecake layer.
Step 7: Repeat the layers, adding more crumbled brownies, followed by cheesecake filling, until the cups are nearly full.
Step 8: Finish with a final layer of cheesecake filling and top with extra brownie crumbs, a generous drizzle of chocolate ganache, and caramel sauce. Add any other desired garnishes like chocolate chips or sprinkles.
Step 9: Chill and serve. Refrigerate the assembled brownie cheesecake cups for at least 2 hours to allow them to firm up and flavors to meld before serving. Enjoy!