Crush the Oreos: Begin by placing the Oreo cookies in a food processor or a durable plastic bag. Crush them until they resemble fine crumbs, perfect for layering. This should take just 2-3 minutes.

Prepare the Cream Cheese Mixture: In a mixing bowl, combine the softened butter, powdered sugar, and cream cheese. Beat with a mixer on medium speed until the mixture is smooth and creamy, which should take about 3-5 minutes.

Make the Chocolate Pudding: In a separate bowl, whisk together the instant chocolate pudding mix and milk until thickened. This usually takes 2-3 minutes. Once thick, gently fold in the Cool Whip until fully combined, creating a luscious filling.

Combine the Mixtures: Carefully stir the prepared chocolate pudding mixture into the cream cheese mixture, combining until completely smooth. Ensure there are no lumps; this creates a perfect creamy texture for the cups.

Layer the Cups: Begin layering your dessert in clear cups. Start with a generous layer of the chocolate pudding mixture followed by a layer of crushed Oreos. Repeat these layers, finishing with a layer of crushed Oreos on top for that classic "dirt" look.

Add Fun Garnishes: For that whimsical touch, decorate each cup with gummy worms and a sprinkling of additional Oreo crumbs. This adds a playful flair that both kids and adults will enjoy!

Chill Before Serving: Cover the cups and refrigerate them for at least 1 hour. This allows the flavors to meld beautifully and the layers to set, ensuring a delightful bite every time.