Hits are hits for a reason. Just play them. Trying to "educate" or "enlighten" your audience will almost always end in failure. Sure, sprinkle a curveball in every now and then. But playing B sides and deep album cuts all night will get your phone to stop ringing faster than anything else. The "moment" when this dawned on me is unclear. I do a lot of fill-in gigs. I can't tell you how many times I hear "Yeah, we play classic rock and blues and stuff....but we're...like....totally different. We don't play the same old tired songs everybody else plays." Yeah, those gigs are usually sparsely attended and there are crickets between some songs.
If you are a cover band, play almost all smash hits. Your audience didn't come out to be educated or have their horizons broadened. They came out to hook up, party, and forget their troubles for a few hours.
Be drama free.
It really hit me when we were playing a wedding at a fancy country club outside Winston Salem some years ago. The wedding organizer was a stress bucket. She was worried to death about every little thing. She kept asking me all kinds of questions about when we went on, how loud we are during dinner, who will announce the wedding party, etc. I simply said to her "We do what we do as often as you do what you do. I promise, we know what to do. Our goal is to make everyone happy and stay out of the way. If you want us to start during dinner, we will play dinner music. If you want us to wait, we'll wait and them hit them with a party. If you want me to announce the wedding party, I got it. All I need is phonetic spellings of any names that aren't pronounced how they are spelled. If somebody in the wedding party needs to say something, send them to me. If you need anything announced, hand it to me and I will handle it. Now, go relax and make sure the wedding party is where they need to be."
About a week later I got an email from her. She said she would use us every time she could. She told me that being able to scratch all things band related off of her to do list made her life so much easier. She said it was the most stress free wedding she had ever done.
When you arrive at any even (party, club date, whatever) FIND whomever is in charge. Assure them that you got this. Tell them to let you know if there's anything you can do to help. Let them know that you know we are all rowing the same boat tonight. Take any band drama outside. Be on time. Have backup plans and spare everything (within reason). You are WORKING when you play. Sure, it's fun. But it's also a BUSINESS. If you ONLY want to have fun, stay in your garage. Make life EASIER for whomever is paying you. Your phone will catch on fire from ringing so much. Turning down several gigs a week is a good feeling. When we ended the last pro band I was in, that's where we were. We turned down more gigs than we took. Our calendar was full right until the end. We were known as the drama free band everywhere we played.