2 small boxes instant vanilla pudding
1 8 oz. package cream cheese, softened
1 c. confectioner's sugar
1 3/4 c. + 1 Tbsp. milk (I used 2%)
1 tub whipped topping (I used Cool-Whip)
1 package chocolate sandwich cookies (I used a store brand cookie. Seriously, it's fine.)
Using a stand mixer fitted with a whisk attachment (or a handheld mixer with wire beaters), beat SOFTENED cream cheese and sugar until smooth. Add in one box of pudding, beat until incorporated, then add in second box and beat until incorporated. SLOWLY add milk with mixer running, blending well to avoid lumps. Beat until the mixture is smooth and thickened (about 30-60 seconds on medium speed). Carefully fold in whipped topping.
Empty contents of cookie package into a large plastic freezer bag (or use a food processor). Using a meat mallet, beat cookies into "dirt." Sprinkle a little less than 1/4 of the cookie crumbs on the bottom of your chosen vessel in an even, then add about 1/3 of the filling. Repeat process, finishing with a slightly thicker layer of crumbs on top. Adorn as desired, then chill until ready to serve.
My mom always served her dirt cake in a plastic novelty coffin for Halloween parties. I have made this dessert for the Superbowl, topping it with dyed coconut shreds for "grass." The coconut grass would also be a cute topping for dirt cake layered inside an Easter basket, topped with plastic, candy-filled eggs. For my niece's autumn-themed Welcome Home party this weekend, I used a flowerpot lined with foil and wrapped in fall ribbon to create an autumn-themed dirt cake, complete with silk flowers. Just be sure to remove the flowers and stick a spoon in before serving or people will not even realize it's dessert (I speak from experience). Be creative and enjoy!