Begin by crushing the Oreo cookies into fine crumbs.
In a mixing bowl, combine the softened cream cheese and powdered sugar until smooth.
Add vanilla extract and mix well.
In a separate bowl, whip the heavy cream until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture.
Layer half of the crushed Oreos at the bottom of a serving dish.
Spread half of the cream mixture over the Oreos.
Pour half of the chocolate pudding over the cream layer.
Drizzle caramel sauce over the pudding layer.
Repeat the layers with the remaining ingredients, finishing with whipped cream and extra Oreos on top.