In a food processor blend your Oreos to fine crumbs.
10 Golden Oreo Cookies
Transfer to a medium-sized bowl. Add the melted butter and use a fork to combine.
2 Tbsp butter
Set out 22 2-oz plastic shot glasses and use a small spoon or teaspoon to press about 1 ½ - 2 tsp of cookie crumbs into the bottom of each shot glass.
oz I use these 2 plastic shotglasses from Amazon.
Prepare your filling.
Filling
In a stand mixer or with an electric mixer stir together cream cheese and vanilla extract. Gradually add cake mix and powdered sugar until completely combined. Scrape down sides and bottom of bowl periodically to ensure ingredients are well-combined.
16 oz cream cheese, 1 tsp vanilla extract, 1 cup + 2 Tbsp white cake mix, ½ cup powdered sugar
With mixer on low-speed, add cool whip and stir to combine. You will need to pause frequently and use a spatula to scrape the sides and bottom of the bowl to make sure it is well-combined. You want the filling to be creamy and smooth -- not lumpy.
12 oz thawed Cool Whip
Transfer the filling to a piping bag fitted with a large tip (I used an Ateco 846 closed-star tip--if you do not have this tip you can simply transfer the filling to a large Ziploc bag, snip a corner off, and pipe the frosting in that way).
Top with sprinkles and cherries, if using, and serve.
Sprinkles and cherries for topping
Keep any uneaten dessert shooters refrigerated in an airtight container.
Notes
*If you don't pipe the frosting in using the specified tip and instead fill the shooters completely you will get fewer dessert shooters