In a large bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until smooth and creamy.
In a separate bowl, whip the heavy whipping cream until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture with a spatula until just incorporated.
Distribute a layer of crumbled brownies at the bottom of each serving cup, using about 2–3 tablespoons per cup.
Pipe or spoon a layer of cheesecake filling over the brownie base in each cup.
Drizzle a thin layer of chocolate ganache and caramel sauce over the cheesecake filling.
Continue layering brownie crumbs, cheesecake filling, and drizzle until each cup is full.
Top each cup with extra brownie crumbs and additional ganache or caramel for garnish.
Cover the assembled cups and refrigerate for at least 1 hour to allow the layers to set.