It's not confusing. People just act like it is. Simon Cowell was extremely popular for humbling people on American Idol. Diddy's having Da Band walk for his cheesecake was joked about for a long time. "That's a one hot album every 10 year average, and that's so lame", "That's why I fucked your bitch you fat mother fucker", the whole Story of Adidon. Corey Holcomb's comments on Lizzo.
Everyone gets the entertainment aspect all those times. Then KS comes up, and people can't understand.
People also say Diddy was as asshole and talk shit about him not really being a good person til this day for that and many other things. Trust when he passes there's gonna be plenty people with not so nice shit to say about him too because they're saying it now. Corey Holcomb...really? The dude who just got in some shit for rape jokes? 2Pac is also seen as having gone over the top for Hit Em Up and shit like that is what led many to say he played a hand in his own demise. You're picking some really bad examples where its clear there was actual backlash to the things in real time.
And even if you want to talk about the translation of those things to real life influence, nobody likes the brash boss who berates their employees like Diddy does. Some people won't like the guy who thinks joking about fucking underage girls is a thing ie Corey Holcomb...and with Kevin Samuels people aren't too fond of someone whose influence has led to dudes thinking they've got a license to go around calling women all sorts of fat bitches and worthless just because he did it on youtube.