re: What would it take to make a great jukebox musical?
One artist that could probably have a very nice jukebox musical would be Meatloaf. That's probably because almost every Jim Steinman song ever written was done so in some sort of theatrical context. I've heard Meat (Mr. Loaf) talk about a musical that Steinman always wanted to do called "Neverland" A lot of his stuff is written with a thought as to how it might work in that.