Since I play the same place five nights a week, four hours a night, the real challenge is keeping it fresh and interesting for repeat customers. Some of these people have been coming to hear me for many years, and that presents a set of problems. They all expect me to remember and play "their" songs, but they also start tuning out if I do the same old stuff every time they come.
I try to learn a new song or two at least every week (used to be every day), but it is often hard to work them in easily.
Let's say I have four tables of regulars. Each has a couple of songs they want to hear. That makes about half a set of songs that I have to do for certain. Then if there are people in cowboy hats, I will do a couple of country songs. There are some older couples that come in expecting to dance to Sinatra or Tony Bennett songs. Younger people respond to newer songs...add a couple of blues or R&B songs if called for...well it keeps you on your toes trying to please them. MUST to do some Elvis. . . then if people from out of town are there, you have to do some Louisiana music, Jambalaya, Toot Toot, Jole Blon, etc., so they get some local "flavor".
Then, the early crowd leaves and another wave takes their place, and the process repeats. I sometimes play Wonderful Tonight three times a night. I know the staff gets tired of it, but it always pleases almost everyone, and I'm not there to play for the staff, or myself for that matter. Then the Boss may come out of the kitchen and expect a Jimmy Swaggart song!
But, every situation is unique. If I play a nursing home, I have a pretty set list of songs in my head that I know for certain will go over and get them at least rocking their chairs a litte. Easy as pie!
Sometimes I wish I were in a Country/Western club and just play that for a couple hours, but of course it would get old too and before you know it a cowboy would come up and ask why I'm playing that Eric Clapton stuff!