There is more than one way to do this. What's right for one isn't necessarily right for the other.
Unlike Eddie, I actually enjoy playing Mustang Sally and the others.
To me, simple songs are like potato chips or Cheetos, junk food for the ears. Not a lot of nutritional value, but a lot of fun to play.
I enjoy nutritious 'art songs' too, and play some of those as well.
I enjoy playing WITH the audience. It's a dialog, it's give and take, and they enjoy what I do, even when I add something for myself. I'm rewarded with love from the audience and enough money to meet my needs.
I don't consider entertaining a sell-out. Other's do. To me, the ultimate sell-out is to take a day job, so I can play 'art music' one day a week for drinks and tips or very low wages. Other's disagree, but that makes us both right.
I had two 'day jobs' in my life while testing what it was to be normal, and to me a bad day at playing music is better than a good day at any other job I can think of.
And I don't agree that the average audience would like whatever you played, as long as you do it well. If I decided to play a set consisting of "Four", "Moonlight Sonata", "Marzy Dotes", "Camptown Races", "Brandenburg Concerto", "Bemsha Swing", and "Night In Tunisia" 90% of the people in the USA wouldn't like it. None of these are considered pop music to me.
During one of my day jobs, I played Sunday afternoons in a jazz band. The guitarist taught at the University of Miami and was in Ira Sullivan's group for a while. Real heavyweights in the industry came to sit in with us because they knew him well. I enjoyed that gig.
For a few years, I played in a top40 band, and ended up being the opening act for top stars of the day. Enjoyed that one too. Plus, I've gigged in a blues band, Salsa band, punk band, sonic-wallpaper band, disco band, psychedelic acid-rock band, show band, symphonic band, and an oldies band. I enjoyed them all.
I just like playing music, and I like entertaining an audience. It's the most fun I can have with my clothes on. YMMV
Insights and incites by Notes ♫