It's the
DM who wears this cap, of course!!
(don't all of you dress like this when you're running the game??)
I took the close-up from the Dungeon Master's Design Kit. NetRodent, if this same piece of art appears on the back of the 1st Ed Forgotten Realms box that is news to me. It doesn't entirely surprise though, as TSR did re-use art from time-to-time.
thanks,
bonk!