Microwave 1/4 cup chocolate chips at 50% power and transfer to a heavy-duty resealable plastic bag. Snip 1/4 inch off a corner and squeeze bag to write R.I.P. on Milano cookies. Refrigerate to set. Divide pudding among 12 dessert cups. Stand 1 cookie in each. Sprinkle cookie crumbs on top of pudding around tombstones.