Yo Dawg, I Heard You Like RPGs...

This is an idea that could be either a lot of fun, or incredibly stupid. It's probably both.

Recently, I was reading a very interesting article on the history of roleplaying games, one that discussed how, although RPGs as we know them - with codified mechanics for conflict resolution, character stats, randomized mechanics using dice or cards, and such - are a recent innovation, we have evidence that people engaged in structured forms of roleplaying for hundreds of years. Rather poetically, much of the surviving records of these traditions date back to medieval Europe, in which roleplaying was a popular diversion among noble courts to pass the time when there was nothing more important going on.

We have to go deeper!

Many of these games involved the use of a ragman's roll - a scroll with a series of ribbons attached to it, each of which could be traced back to a particular passage. Each participant would pick one of these ribbons and follow it back to the passage it corresponded to, which would describe a character or scenario. Then, they would have to take the role of that character, talking and acting as they would do so, while interacting with other players doing the same. (Incidentally, this is where the term "rigmarole" comes from).

It's a fascinating bit of history, and one of the many, many examples of interesting medieval trivia that popular culture is woefully unaware of. But it also means something that carries a lot more potential. There is a nonzero chance that the people in your medieval fantasy RPG world play RPGs.

I think that, when approached with the right mindset and the right players, a session in which the party takes part in a game of Ragman's Roll could be a lot of fun. For the session, the PCs would be tasked with stepping into new roles and personas, acting as they would interpret the roles from within the context of their character traits. Essentially, the players would end up playing characters who are themselves playing characters. Instead of making decisions that they feel their characters would, they would have to make decisions they feel that their characters would feel their characters would.

There's a number of different ways to do it, too. It could simply be used as a framing device for a one-shot session in the middle of an existing campaign, such as if one of the players can't make it to the table - the players would be using new PCs in a self-contained story, but that story could also exist within the context of the greater campaign as a scenario played out by the original PCs. It could be an opportunity for players to experiment with new PC ideas they've been developing, or to reuse a PC from a previous game, perhaps with some tweaks due to being filtered through the PC taking their role. Such a one-shot wouldn't even need to use the same system, and it could be a way to try out a different game without committing to a full campaign.

It's not like we don't enjoy
playing old games anyway

Alternatively, a game of Ragman's Roll could be a part of an adventure, or a plan by the PCs - perhaps they need to infiltrate a noble court in order to gain intelligence, and in order to blend in or to get closer to potential informants, they need to partake in the game. Since these games usually took place among courts, and most interactions between players appear to have been settled through in-character debates and discussion, this could present a unique spin on a social encounter, offering the PCs with different challenges and encouraging some interesting roleplay. Integrating oneself with nobles, knowing the right things to say and the right people to cozy up to, can be a challenge already - now, imagine doing all that while you're expected to pretend you're someone you aren't!

Obviously, a scenario like this wouldn't be for everyone. Roleplaying as someone roleplaying as someone else would no doubt be a challenging task, and it could easily get confusing for some players to keep track of balancing both how their character would behave and how their character's character would behave, to say nothing of the code-switching between three different roles. It can already be difficult to distinguish in-character from out-of-character talk at the table; now there's another layer beyond that. All these challenges would be present even if Ragman's Roll is used as a low-stakes diversion - if the PCs are actually trying to gain something through the game, that could make things even trickier. Some people might find the whole exercise a bit meta, too, but that's where you can bust out that this is all historically accurate.

But I do think, when approached with the right mindset, it could make for a very memorable and enjoyable session. A lot of roleplayers might enjoy the challenge of roleplaying someone roleplaying, and such an opportunity to get deeper into their characters' heads (or maybe that's just my theater kid self talking). At the very least, it'd probably create some amusing chaos if combined with alcohol, which I'm sure was what medieval people got out of it anyway.