In a food processor, pulse 6 Cheryl's Pumpkin Chocolate Chip cookies until they are crumbs. Transfer the crumbs to a bowl. Add the sugar (omit if you like a less sweet crust) and melted butter. Mix until incorporated. Press the cookie dough into a 9- or 10-inch deep-dish pie pan and put it in the refrigerator to set while you make the rest of the ingredients. (This can be made 1 to 2 days in advance and kept covered in the refrigerator.)
In a food processor (or standing mixer), mix a packet of instant chocolate pudding with the heavy cream on high for 1 to 2 minutes or until very thick. Add pumpkin puree, cream cheese, frozen whipped topping, vanilla, and pumpkin spice. Mix on low until all ingredients are incorporated.
Remove the pie crust from the refrigerator and fill it with the pumpkin-chocolate mixture. Cover lightly and return to the refrigerator to set for at least 4 hours or overnight.
In a food processor, pulse one Cheryl's Pumpkin Chocolate Chip cookie. Place the crumbs in a plastic baggie and snip off the corner with scissors.
Remove the pie from the refrigerator. Ice it with the remaining frozen whipped topping. Place one Cheryl's Pumpkin Chocolate Chip cookie decoratively in the center of the pie. Holding the plastic baggie of crumbs with the hole facing downward, make a concentric ring with the cookie crumbs at the outer edge of the pie.
Use a sharp knife to cut the pieces before using a pie server to remove slices.