Crush the Oreo cookies using a food processor or by placing them in a resealable plastic bag and using a rolling pin until you achieve fine crumbs.
In a large mixing bowl, combine the instant chocolate pudding mix with the cold milk. Whisk until smooth and let it sit in the refrigerator for 5-10 minutes to thicken.
Once the pudding has thickened, gently fold in the thawed Cool Whip until fully combined and fluffy.
In clear cups or bowls, layer the crushed Oreo cookies at the bottom, followed by a generous scoop of the pudding mixture. Repeat the layers until you reach the top, ending with crushed Oreos.
Sprinkle chocolate sprinkles over the top layer and decorate with Halloween cookies, gummy worms, M&M's, and candy corn for a spooky appearance.
Place the cups in the refrigerator for at least 1 hour to chill before serving.
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Notes
Store in an airtight container in the refrigerator for up to 3 days.