Begin by decorating the Milano Double Chocolate Cookies to create spooky tombstones. Use black frosting or an edible marker to write 'RIP' on each cookie. Set them aside to allow the frosting to set while you move on to the pudding layers.

In a large mixing bowl, whisk together the chocolate instant pudding mix and 2 cups of cold milk for about 2 minutes until it thickens. Gently fold in 1 cup of Cool Whip until fluffy, creating a light and creamy pudding.

Using a food processor or a zip-lock bag and a rolling pin, crush the Oreo cookies into fine crumbs. Ensure there are no large pieces remaining.

Grab clear drinking cups to showcase the layers. Start with a layer of crushed Oreos, press some googly eyes against the sides, then spoon in a layer of the creamy pudding. Repeat until the cups are nearly full, finishing with an Oreo layer on top.

Insert the decorated Milano cookies into the pudding to stand up as tombstones. Scatter the candy pumpkins on top for color, and add gummy worms if desired.

Place the assembled cups into the refrigerator for at least 30 minutes to allow the pudding to set and flavors to meld.