Preheat oven to 350 degrees and grease a 9-inch pie pan or springform pan.

Stir together the Oreo crumbs and melted butter until well combined. Press the crust mixture into the prepared pan, smoothing into a uniform layer. Bake in the preheated oven for 10 minutes, then allow to cool at room temperature for 15 minutes. Place in the fridge while you make the filling.

In a medium bowl, stir together the pudding mix with the cold milk, espresso powder, and peppermint extract, whisking for 1-2 minutes until the mixture is smooth. Set in the fridge to set for at least 5 minutes.

While the pudding is setting, add the cold whipping cream to a stand mixture fitted with the whisk attachment, and whip the cream until stiff peaks form.

Fold the chocolate pudding into the whipped cream until well combined, be careful not to deflate the whipped cream too much.

Pour the mixture into the cooled pie crust, smoothing as you go. Cover and refrigerate for another 4 hours or overnight. Garnish with whipped cream and crushed candy canes, then serve.