Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
- Cream the butter, brown sugar, and granulated sugar on medium speed for 3-4 minutes until light and fluffy.
- Add eggs one at a time, beating well after each addition. Mix in vanilla extract.
- In a separate bowl, whisk together flour, black cocoa powder, 2½ cups Oreo crumbs, baking soda, baking powder, and salt. Gradually add to the wet ingredients, mixing until just combined.
- Scoop out approximately 3 tablespoons of dough, roll into balls, and roll in the remaining Oreo crumbs. Place the dough balls on the prepared baking sheet.
- Refrigerate dough for 2 hours. Then, bake for 12 minutes or until edges are set. Cool on the baking sheet for 10 minutes before transferring to a wire rack.
- Prepare the frosting by whisking together instant chocolate pudding mix, heavy cream, milk, powdered sugar, cocoa powder, and vanilla extract until smooth and thickened. Refrigerate until ready to use.
- Once cookies have cooled, spread chocolate pudding frosting over each cookie, sprinkle with Oreo crumbs, and top with a gummy worm.