Bosses are the butt of our jokes and bear the brunt of our frustration — but there are some good ones out there, and we celebrate them every October 16, on National Boss’s Day. Our term for the person who sends out memos and signs our paychecks first entered American English around 1640, where it referred to a ship’s captain. In both the 1880s and then again in the 1950s, “boss” was also used slangily to describe something cool or excellent, so if you are blessed with a (metaphorically) bitchin’ boss, you could call ‘em a boss boss.