I’m not sure Prince and Lady Gaga belong on there because their intent was always popular demographic sales. U2 may be the single most over-rated band of all time and Bono is extremely self important, but I don’t think they’ve made records specifically to target a demographic … i.e. let pop trends determine song format.
I have to go back a ways … but lets take Journey. They were a very jam oriented band, but were searching for popular acceptance and hired a singer “Steve Perry”, and moved closer to pop song structures. Infinity was the first result. That album worked in both directions. Accessible, but still interesting/creative songs. However, the drummer and keyboard player were totally hating on it as they went through the process for the next pop fest album, and quit. Even Neal Shon hated it, but was digging the response from the audience, so he continued to slug out the pop dribble.
That’s a sell-out. However, I’d gladly sell out for those pay checks.