I play a mix of "songs I know many people like" (based on requests and response over many years), and "songs they might not have heard as much, but might like". I often good good response and comments on the less-often-heard ones, but not always. Sometimes I'm surprised by what song(s) someone says they particularly liked!

I also actively take requests at nearly every gig ... I can't always play ALL of them, but I tend to be able to handle ~80-90% of them. Asking for requests, I think, involves them a bit more actively than not taking requests, and gives me some input on what they want to hear. At some gigs, that are for a "special theme", I will more likely not take as many requests, but play "to the theme" (such as Italian Night or 50's Sock Hop Dance, or Classical Concert, or other specific themes requested for an event by the client).

I have a lot of set lists I have made (from about 1000 songs in my repertoire), and I rotate through them a lot, i.e. try to play different set lists each time at a venue. I keep a little "log" (a file on my computer) where I type in a quick summary of "what I played" at a given place on a given date ... to help me vary the music for them each time I play at that particular venue. So I don't play the same songs at the same place too much, except certain favorites they always request. . .

Jim