With black frosting (with a small frosting top) or with an edible marker, write RIP on each of the Milano cookies creating a tombstone. Set aside.
In a stand mixer, whisk together pudding mix and milk together on medium speed for 2 minutes.
Fold in cool whip until well blended.
Crush Oreos until they are fine crumbs using a food processor.
Sprinkle 3-4 TBSP of crumbs into the bottom of 6 clear 9 oz. clear plastic cups.
Press a few googley eyes around the edges between the crumbs and the cup so it looks like they are peaking out.
Spoon in a layer of pudding on evenly on top.
Repeat the last three step one more time.
End the layers by sprinkling more crumbs on top until they almost reach the lip of the cup.
Firmly insert one cookie tombstone into the center of each pudding cup.
Gently press in a candy pumpkin beside each tombstone.
Embellish with gummy worms if desired.