So im pretty new to being a DM but i had this interesting idea for a small d&d game where a bartender is telling people a story about either a special item he has hung up on a wall or something.

Its a little complicated but i wanted to try something where the players had to make two characters. The first character is the normal hero like character but the second character is just a normal person, maybe even classless characters or just average people. Basically the average people are listening to the bartenders story and time to time the bartender breaks away from the story to either do a bit of work or maybe mess with the people listening by making them play a small game or something. Every time he does this tho it could change the output of the story.

The story he is telling tho has the other set of characters the players made, fighting and doing what they can to achieve the goal in front of them while also adjusting themselves as the story goes on.

I feel like i might be just making this overly complicated but that's the idea at the least and i was wondering if this would even work at all.

A story within a story within a story.  If you can tell me how I got three stories, you should be capable of doing it right.