Well, it probably started with a ragman, that is, a man who collected rags to sell to...well, anyone who wanted rags. A paper maker, perhaps.
This ragman was a good ragman, but nothing else is known about him except his character is thought to have been used in Mediaeval times in a sort of fortune-telling game. The idea was that you had a long piece of paper or parchment on which were written a list of descriptions of various characters, each description literally having a string attached beside it. The idea was that you rolled up the list into a scroll that had the strings dangling from it, and then everyone chose a random string. The scroll would then be unrolled, thus revealing everyone's true character. Or something equally hilarious.
The list was traditionally headed by the description of Ragemon the Good, and it looks as though a rigmarole was originally a ragemon roll.
Was the game so boring that it became a byword for long complicated recitals of instructions or of nonsense?
Well, probably not, especially as the unrolling of the scroll must have been quite fun as everyone would have had to have kept hold of their string.
What seems to have happened with the word rigmarole is that the sight of legal documents, also written on scrolls and with the seals of all sorts of important people dangling from it on ribbons, reminded people irresistibly of good old times playing with ragman rolls. And so the term was tranferred to legal documents - and, sadly, a name for a good game turned into a term for a long boring or ridiculous list.
Word To Use Today: rigmarole. An easy word to use these days, when we have so many computers to help us do things.