Place the chocolate cookies in a resealable plastic bag and crush them into fine crumbs using a rolling pin or the bottom of a glass; set aside.
Spoon the crushed cookies evenly into the bottoms of your serving cups or glasses, pressing gently to form a firm base.
In a mixing bowl, beat the softened cream cheese with powdered sugar and vanilla extract until smooth and creamy, about 2 minutes.
In a separate bowl, whip the heavy cream until soft peaks form, then fold it gently into the cream cheese mixture to create a light and fluffy filling.
Spoon or pipe the creamy filling over the cookie crust in each serving cup, filling almost to the top.
Optionally, garnish with extra cookie crumbs or chocolate shavings for decoration.
refrigerate the cups for at least 30 minutes to allow the flavors to meld and the filling to set, then serve chilled and enjoy.
