Crush the Oreos: Add cookies to a zip-top bag and crush with a rolling pin, or pulse in a food processor. Aim for a mix of fine crumbs and small chunks. Set aside.

Make the pudding: In a large bowl, whisk instant pudding mix with cold milk for 2 minutes until thick. Let it sit while you make the cream layer.

Beat the cream cheese mixture: In another bowl, beat softened cream cheese and butter until smooth. Add powdered sugar and vanilla, and beat until fluffy with no lumps.

Combine the layers: Fold the cream cheese mixture into the pudding until smooth. Gently fold in whipped topping until fully blended and airy.

Set up an assembly line: Arrange cups, crumbs, and filling. It goes quickly once you start.

Layer the cups: Spoon 1–2 tablespoons of Oreo crumbs into the bottom of each cup. Add a layer of the creamy filling (about 1/4 cup). Repeat with another layer of crumbs and another layer of filling.

Top with “dirt”: Finish each cup with a generous sprinkle of Oreo crumbs. Press a gummy worm or two into the top if using.

Chill: Refrigerate at least 1–2 hours before serving. This helps the flavors meld and the layers set.

Serve cold: Keep the cups chilled until guests arrive. Hand out spoons and watch them vanish.