So, during our last session for that ToD campaign I’m running a few days ago, the Glass Breakers were up against some more undead not long after taking on a bunch of ghouls and ghasts last session. The undead they were fighting this time around consisted of shadows, specters, a poltergeist, and a flameskull.

At one point, Jameson (gnome barbarian/ranger) walked away from the Flameskull, so I had it make an opportunity attack by bashing itself onto the barbarian, which technically counted as an unarmed strike. The chances of even hitting were literally 1 out of 20, as the flameskull had a -5 Strength modifier, meaning I had to roll a Natural 20 for it to even hit.

I ended up rolling a Natural 20, so Jameson ended up taking like a point of fire damage or two (since the flameskull was, as the name implies, covered in flames).

It was easily the dumbest thing I’ve ever rolled a Natural 20 on.