Rick
"I'd give five years of my life to have five minutes with him and play one of his 'requests.'"

Me too. My dad always requested Jerry Jeff Walker's Mr. Beaujangles. After awhile I got rather bored with it. Now I wish I had been a little more creative and imaginative with arrangements to keep me interested in the song.

Therein, I think, lies the answer, partially. While on the one hand as a performer you want to include some familiar material, there must be a way to make an old chestnut interesting to you as a performer, and at the same time satisfy your audience.
Jim