To focus on only the recent past: we only know about radio plays (determined by cronyist industry dealings) and about record/8track/cassette/CD/iTunes sales (where a record sale could represent a purchase due to virality—i.e. a purchase for status-signalling/watercooler-conversation/joining-a-subculture reasons, but where nobody actually listens to their purchase more than a few times; or it could represent a song everyone loves and puts on repeat all day every day. And a purchase could represent a fad that fizzles out; or a classic in the making.)
We can talk about what the top40 billboard charts were doing back then, but what people were “most listening to” is very likely a wholly different list with little intersection to the billboard chart. Just like this Spotify most-played list is actually an almost-entirely-distinct list from the current radio top40!
https://en.m.wikipedia.org/wiki/List_of_Billboard_number-one...
I’d say the quality of “most listened to” music peaked in the 80’s, with each decade that followed being the worst ever.
Most of my favorite artists are from the 90’s-2010’s, with a few exceptions scattered in the 40’s, 70’s and 80’s.
It could be that music got more diverse in the 90’s, and the billboard chart stopped being broadly relevant.