Place the crushed cookies in a mixing bowl and set aside.
Microwave the chocolate in short bursts until melted and smooth, then let it cool slightly.
In a separate bowl, beat the softened cream cheese and powdered sugar together until creamy and smooth, about 1-2 minutes.
Pour the melted chocolate into the cream cheese mixture and fold until well combined, creating a silky base.
In a chilled bowl, whip the heavy cream until stiff peaks form, about 3-4 minutes.
Gently fold the whipped cream into the chocolate-cream cheese mixture, retaining as much air as possible for fluffiness.
Spoon the creamy mixture into individual serving cups or glasses, filling them about three-quarters full.
Sprinkle the crushed cookies evenly over the top of each cup, creating a crunchy topping.
Refrigerate the cups for at least 30 minutes to allow them to set and chill thoroughly.
Remove from the fridge, garnish with additional crushed cookies if desired, and serve chilled.