Captain Russ....
I have read and re-read your post regarding jazzing up the Tennesee Waltz and your interaction with the young trumpet player from Stan Kenton's band. Wow! Great story with a moral many of us have had to learn the hard way.
Living in an area of the country that has a large retirement population (Florida) I am torn between playing the generic versions of the same old songs that are expected and trying to present something fresh - such as 1) Jazzing up a song they know, or 2) slipping in a more contemporary, less familiar song once in awhile. I will try either of the two occasionally and watch the reaction. 90% of the time it doesn't get the desired reaction and I move back into the Safe Zone. But, every once in awhile I get a "Wow" reaction and they will request it at my next visit.
I guess all of us want to stand out, in some way, from our counterparts in the biz, if nothing more than to create our own identity and avoid the boredom of repetition. The only time I do any Jazz is during a cocktail or dinner hour, where the volume is light and the song is light and breezy. Once the dancing starts, its the old familiar that sells and gets me re-booked.
I think that is also true of the Jazz guys. Once Take Five was a hit, Dave Brubeck could not do a concert without the fans screaming for it. Anything less met with great audience disapointment.
Eddie