Step 1: Prepare the Crust: In a medium bowl, mix the chocolate cookie crumbs and melted butter until the mixture resembles wet sand. Press the mixture firmly into the bottom of a 9x13-inch baking dish to form an even crust. Place in the refrigerator and chill for 10–15 minutes to set.
Step 2: Make the Cream Cheese Layer: In a separate bowl, beat the softened cream cheese and powdered sugar until smooth and creamy. Gently fold in 1½ cups of whipped topping until well combined. Spread this mixture evenly over the chilled crust, making sure to cover edge to edge for a solid base.
Step 3: Add the Cherry Pie Filling: Carefully spoon the cherry pie filling over the cream cheese layer. Use the back of the spoon to gently spread it across the surface, taking care to keep the layers distinct.
Step 4: Mix and Spread the Chocolate Pudding Layer: In a clean bowl, whisk together the instant chocolate pudding mix and 1½ cups of cold milk for about 2 minutes, or until thickened. Let it sit for a minute or two if it needs to firm up more. Once ready, spread it evenly over the cherry layer.
Step 5: Add the Final Layer of Whipped Topping: Spread the remaining 1½ cups of whipped topping evenly over the chocolate pudding layer.
Step 6: Garnish (Optional but Recommended): If desired, add some chocolate shavings, mini chocolate chips, or a few extra cherries on top for garnish.