The most crowd-disappointing show I witnessed as a youth was in the early '70s. John Mayall (a man who changed band members as frequently as most people change underwear) was fronting his new Jazz-Blues Fusion organization. Musically they were exceptional, tight and played off each other well, improvising. However, the crowd was 'rock 'n roll' oriented, and like that Dire Straights song, they really didn't give a damn about a trumpet playing band (in this case, Blue Mitchell).
A year or two earlier, John had had a 'big' hit (LOL) with his Turning Point band, and that's what the crowd wanted to hear. They wanted John to play Room to Move. At the end of the show, the crowd was shouting for it, asking him to play it as an encore. John stopped the music, lecturing the audience (I remember his words to this day) that that was 'old', he'd moved on, and wasn't going to play it. The crowd booed him.
I get what John was saying, but at the same time the audience was paying their salary, and would it have hurt him and the band to spend three or four minutes on that tune? I don't think anyone left happy that night. John, his band, and certainly not the audience.
I've watched a few of John's 'recent' YT shows, and he is now happy to play the tune everyone recognizes as his signature piece. Go figure.
Of note, in a case of weird programming, the 'supporting' act was a band called Poco. A southern country-rock oriented combo. Talk about a mismatched lineup. Final note--I think tickets were three or four dollars. But you could buy a gallon of gasoline for a quarter back then, on a good day.