Place 36 chocolate sandwich cookies in a food processor and pulse until they become fine crumbs. Transfer the crumbs to a mixing bowl, pour in the melted butter, and stir thoroughly until the mixture resembles wet sand and holds together when pressed. Press the mixture evenly into a 9-inch pie dish, making sure to go slightly up the sides to form a sturdy crust. Place the crust in the freezer while you prepare the filling.

In a clean mixing bowl, combine 1 cup heavy cream, 1 teaspoon peppermint extract, and ½ cup powdered sugar. Using an electric mixer on medium speed, beat the mixture until stiff peaks form (this takes about 3-4 minutes). The whipped cream should hold its shape when you lift the beaters. Set this aside in the refrigerator.

In a separate bowl, mix the instant vanilla pudding mix with ¾ cup whole milk. Whisk vigorously for about 2 minutes until the mixture becomes smooth and starts to thicken. The pudding will continue to set as it sits.

In a small cup, combine the unflavored gelatin with 1 tablespoon of hot water. Stir until the gelatin is completely dissolved with no granules remaining. This helps stabilize the filling so it sets properly when frozen.

In a large bowl, beat together the softened cream cheese, 6 tablespoons softened butter, and ½ cup powdered sugar using an electric mixer. Beat on medium-high speed for 2-3 minutes until the mixture is light, fluffy, and completely smooth with no lumps.

Add the prepared pudding mixture and dissolved gelatin to the cream cheese mixture. Mix on low speed until everything is smoothly incorporated and the filling has a uniform consistency.

Gently fold in half of the prepared peppermint whipped cream (save the other half for another use or enjoy it separately). Add the mini chocolate chips and crushed candy canes, folding carefully with a rubber spatula until everything is evenly distributed and the filling remains light and airy.

Remove the chocolate crust from the freezer. Spread the peppermint filling evenly into the prepared crust, smoothing the top with a spatula. Cover the pie with plastic wrap or a pie dish cover. Place in the freezer for at least 6 hours or overnight until the filling is completely set and firm.

Just before serving, prepare the whipped cream topping by beating 2 cups heavy cream with ¼ cup powdered sugar until stiff peaks form. Spread this whipped cream evenly over the frozen pie, creating swirls or peaks for a beautiful presentation.