Hey Bernie,
Many of us face this issue. I have places I play weekly with the same people every time and I have other places I play monthly, again with most of the same people. Over the years I have established more songs I play than I have time to even go through to find the most popular. What I have done is setup over 50 play lists with songs from the era my audiences understand and request. There are always some tunes in any play list that can be found in several other lists because they are the ones most often requested or are known to everyone. I have an added problem in that I play very few songs from memory so I have to also setup leadsheets for each playlist and have them organized for good flow. It takes time and things change for various reasons. I am constantly changing my lists and, like you, it often is because I get tired of the same old songs day after day. However, I always keep in mind who I play for when I make changes. During a gig I let folks know to let me know if there is a song they want to hear and I always make sure I play any of those requests.

This brings to mind my early days playing with several very well nationally known big bands. We ALWAYS played the same songs, in the same order, and exactly the way they were recorded note for note. The audiences expected to hear these big hits from these bands and were there to hear just that. From a band member's point of view it got real old fast - but that was the business - giving them what they came for.

Perhaps each of us is hired today because we have a flare for playing certain songs or genres that rings true with the people who hire us. If that is true then playing the same songs might not be a bad thing - at least from a business point of view.

Deane