It’s just a case that music tastes have changed in the last 20 years and they are booking different acts to reflect that. All I can say is I’m thankful I was in my late teens/early 20s in the late 90s/early 00!
Basically if you listen to an artist repeatedly on the run up to seeing them they are typically in the top 5. I generally just let the algorithm do its thing and auto play relevant songs so most of my listening time is just that.