Place the Oreo cookies in a food processor and pulse until they are finely crushed, resembling dirt. Set aside.
Make the Pudding Layer:
In a large mixing bowl, whisk together the instant chocolate pudding mix and cold milk for about 2 minutes, or until thickened. Refrigerate for 5 minutes to set.
Create the Cream Cheese Layer:
In another mixing bowl, beat the softened cream cheese, unsalted butter, powdered sugar, and vanilla extract until smooth and creamy. Set aside.
Prepare the Whipped Cream Layer:
In a chilled bowl, beat the heavy whipping cream and granulated sugar with an electric mixer on high speed until stiff peaks form.
Assemble the Dirt Cake:
In your clean flower pot or serving dish, start by spreading a layer of the crushed Oreos at the bottom.
Next, spread half of the pudding mixture over the Oreos.
Follow with a layer of the cream cheese mixture.
Spread a layer of whipped cream on top of the cream cheese layer.
Repeat the layers, starting with the crushed Oreos, then pudding, cream cheese mixture, and finishing with whipped cream.
Sprinkle the remaining crushed Oreos on top to resemble dirt.
Decorate:
Insert gummy worms or candy insects into the “dirt” to create a fun and playful look. If desired, add plastic flowers or garden-themed decorations to enhance the appearance.
Chill and Serve:
Refrigerate the Dirt Cake for at least 2 hours or overnight to allow the flavors to meld and the layers to set.
When ready to serve, use a garden trowel or a large spoon to scoop out portions, ensuring each serving has a bit of each layer.