Because the service they give to the Status Quo, to the Global Elites, to the Empire is very valuable.
All entertainers ain’t paid. I know many working class artist, entertainers, and athletes, poor ones too.
If you are willing to promote the American Way (and yes, gangsterism/thugism/anti-womanism is the American way) you can get them big dollas; if you are a principled individual you will not, if you get to the top and you wake up the System will begin to systematically break you down, isolate you, ignore you, demonize you, etc.
So, distraction the masses, feeding the masses a false sense of belonging, offer an empty narrative of opportunity or a chance to go from Rags to Riches if you got dope rhymes, or if you really good at “sling(ing) crack rock, or got a wicked jump shot” will get you P.A.I.D!
Since the first Industrial Revolution the Elites have progressively chosen to move away from brute force and open cohesion to keep the masses in check to using propaganda and mass indoctrination to maintain the Status Quo.
You will find that the prominence and wealth of entertainers grew along side this change in elite methodology.
So, Jay & Bey, Jordan, Oprah, Kayne are more than just talented and gifted individuals, they are well-paid propagandist for the Global Elites and the Systems of White Domination.
There is so much more to say, but this is a basic overview of this issue.
One of the authors and philosophers who break this shit down is Jacques Ellue, check out his famous text: Propaganda: The Formation of Men’s Attitudes.