In food processor, pulse cookies until mostly crumbled. Add butter and pulse until completely blended (fine crumbs).
Using a small spoon, gently pack about 2 tsp of the crumbled cookie/butter mixture into the bottom of each shot glass (30 shot glasses total). Reserve any extra crumbs to sprinkle on top of finished product.
In KitchenAid or with an electric mixer, cream together cream cheese, pumpkin puree, and brown sugar until well-combined.
Add in pumpkin spice and stir well.
Stir in vanilla extract.
With mixer on low speed, slowly add in powdered sugar, pausing to scrape down the sides of the bowl as needed.
With mixer on low speed, gently mix in 12 oz Cool Whip. Use a spatula to scrape down the sides and complete the mixing by hand.
Using either a large piping bag with a 1" tip or a Ziploc bag with a 1" hole cut in a corner, pipe filling into the prepared shot glasses on top of the gingersnap crust, evenly dividing mixture among all shot glasses.
Pipe the remaining 8 oz Cool Whip on top of the pumpkin pie cheesecake filling, evenly dividing between shot glasses. This can be done with either a Ziploc bag with a hole cut in a corner of it or with an icing bag and a star-tip (which was used for the topping in these pictures).
Sprinkle remaining cookie crumbs over tops of dessert shooters before serving (be sure to keep refrigerated if not eating immediately).