Crush the Oreo cookies in a food processor or by placing them in a ziplock bag and crushing them with a rolling pin until they are finely ground.
In a mixing bowl, combine the Oreo crumbs with the melted butter. Mix until the crumbs are fully coated with the butter.
Press the Oreo mixture into the bottom of a 9-inch springform pan. Use a flat-bottomed glass or measuring cup to press the crumbs firmly and evenly into the bottom of the pan. Chill the crust in the fridge while you make the filling.
In a large mixing bowl, beat the softened cream cheese until it is smooth and creamy.
Add the granulated sugar and cocoa powder to the cream cheese and continue to beat until the mixture is well combined and smooth.
Mix in the sour cream until everything is well combined.
Fold in the thawed Cool Whip until the mixture is light and fluffy.
Pour the filling into the prepared Oreo crust and spread it evenly with a spatula.
Chill the cheesecake in the fridge for at least 8 hours or overnight.
Once the cheesecake is fully chilled, remove it from the springform pan and place it on a serving plate.
In a large mixing bowl, whisk the heavy cream and powdered sugar together until soft peaks form.
Pipe or spoon the whipped cream around the edges of the cheesecake.
Spoon the cherry pie filling on top of the cheesecake and spread it evenly to cover the surface.
Sprinkle chocolate shavings on top of the whipped cream and cherry pie filling.
Slice the cheesecake into servings and serve chilled.