The noun rigmarole (referring to long, convoluted stories or procedures) is a Kentish colloquial alteration of the Middle English phrase ragman roll, which was a type of parchment with character descriptions written on it that was used in a gambling game where the scroll was unrolled and the passage read out loud. People in the Middle Ages did weird things for fun. The game, which was earlier called Rageman or Raggeman, has debated origins, but was most likely a name from one of the descriptions (that's ultimately French in origin). The current definition arose from a sense of rambling something off, which was eventually extended to time-consuming things in general later on. According to Google NGrams, rigmarole was popularized in the 1820s and 1830s and has recently experienced a resurgence in usage.
Hello! I'm Adam Aleksic, a sophomore studying linguistics and government at Harvard University, where I founded the Harvard Undergraduate Linguistics Society. I also have disturbing interests in politics, vexillology, geography, board games, conlanging, and law.