Crush the cookies. Place the chocolate sandwich cookies in a zip-top bag and crush with a rolling pin until you have fine crumbs with a few small chunks. You can also pulse in a food processor. Reserve 1/2 cup of the crumbs for the final topping.
Make the pudding. In a large bowl, whisk the instant pudding mix with cold milk according to package instructions. Let it thicken for 5 minutes.
Optional mousse upgrade. If using cream cheese, beat the softened cream cheese with powdered sugar and vanilla until smooth.
Fold in the whipped topping.
Combine. Gently fold the whipped topping (or the cream cheese mixture with whipped topping) into the set chocolate pudding until smooth and airy. This creates a light, mousse-like texture.
Assemble the base layer. Spoon 1–2 tablespoons of cookie “dirt” into the bottom of each cup. This prevents sticking and adds crunch.
Fill the cups. Divide the pudding mixture among the cups, leaving about 1/2 inch at the top for the cookie layer.
Tap cups lightly to settle.
Add the dirt topping. Sprinkle the remaining cookie crumbs over each cup to fully cover the pudding. You want a nice, even “soil” layer.
Create the footballs. If you have gummy footballs, place one on each cup. If not, use chocolate-covered almonds and draw laces with white gel.
Let the laces set for a few minutes.
Optional grass detail. Toss shredded coconut with a few drops of green food coloring until you get a turf-like color. Sprinkle a small pinch around the “football” for a field effect.
Chill and serve. Cover and refrigerate for at least 1 hour to set the layers and enhance flavor. Serve chilled with spoons.