Place a medium mixing bowl and beaters in the freezer to chill while preparing the crust and filling.
To prepare the crust:
Preheat the oven to 350°F. Pour the cookies and powdered sugar into the bowl of a food processor. Pulse until the mixture is fine even crumbs. Add the melted butter and process again until the mixture is evenly moistened and resembles wet sand.
Transfer the crust mixture to a 9-inch pie pan. Using the bottom of a dry measuring cup firmly press the crumbs into the bottom and up the sides of the pan. Bake until set and fragrant, about 10 minutes. Remove to a wire rack to cool completely before filling. The crust can be made 24 in advance and refrigerated until needed.
To prepare the filling:
Using a stand mixer fitted with the whisk attachment combine the powdered sugar, cream cheese, 3 tablespoons of heavy cream (reserve remainder for the next step), creme de menthe and creme de cacao on low speed until combined. Increase speed to medium-high and whip until fluffy, about 1 minute.
In a chilled mixing bowl whip the remaining heavy cream on medium-low until foamy. Increase the speed to high and whip the cream until stiff peaks form. Gently fold half the whipped cream into the cream cheese taking care not to deflate the airy mixture. Add all remaining whipped cream and fold until no white streaks remain. Spoon the filling into the prepared, cool crust and spread to an even layer. Refrigerate until set, about 2 hours.
Prepare the topping:
In a chilled medium mixing bowl combine the powdered sugar, vanilla and heavy cream. Using an electric mixer blend on medium-low speed until foamy. Increase the speed to high and whip until silky stiff peaks form. Spread, pipe or dollop the whipped cream over the pie filling. Sprinkle crushed cookies over the top to decorate. Refrigerate or serve immediately.
Notes
Refrigerate leftovers.
The pie can also be frozen for up to two months
Nutritional information is calculated using an ingredient database and should be considered as an estimate. When multiple ingredient alternatives are given, the first listed is calculated for nutrition. Garnishes and optional ingredients are not included.