I agree, Dylan would be a great choice. In fact, he'd be a great choice for multi-denomination chips.

AS for a second issue, I don't know of anyone other than Petty. I think the Stones would be a good choice for an LE, since they already have a $25 "house chip" (if it's limited, it's limited to about a billion). I think Petty has an LE $5 and a House $100 (I'm sure someone will correct me if I'm wrong).

The very ideal of the Stone playing The Joint (or any of the other clubs they're doing on the tour) is incredible. The Joint capacity for that show will be a mere 1500 people.