Place vanilla wafers or chocolate cookies in a food processor or inside a plastic bag and crush into fine crumbs using a rolling pin or the bottom of a heavy object.
In a large mixing bowl, beat the softened cream cheese with powdered sugar until smooth and fluffy.
Whip the chilled heavy cream and vanilla extract in a separate bowl until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture until fully combined and smooth.
Mix in the melted and cooled chocolate chips into the creamy filling for a rich chocolate flavor.
Spread a layer of crushed cookies evenly in the bottom of the serving dish to resemble dirt.
Pour half of the creamy filling over the cookie layer, smoothing it out with a spatula.
Add gummy worms randomly on top of the filling, pressing them slightly into the layer so they stay hidden beneath the surface.
Repeat the process with another layer of crushed cookies, followed by the remaining filling, creating a layered effect.
Finish with a generous sprinkle of crushed cookies on top to resemble fresh dirt.
Chill the assembled dirt cake in the refrigerator for at least 2 hours before serving to allow flavors to meld and for the dessert to set.
Serve slices with extra gummy worms or spooky decorations if desired, and enjoy the chaotic, creepy treat!