A couple of things:
First, you're absolutely dead-on when you reference the "phony sayings that let you know someone is virtue signalling." That was sort of my point...to demonstrate how these comedians who claim they are being "oppressed" now sound like a bunch of whiny babies. They simply don't want to acknowledge how they benefit from iconism. In real life, I don't go around telling people to "Be better" / "Do better" / "Check your privilege" -- those references were a mocking of the Hyperwoke Left, on my part.
Secondly, as I specified in the article, the privilege that comedians have is a variation of the privilege that celebrities and famouns people in general have. Not every comedian abuses that privilege. Many comedians understand that there are real people in their audiences whose lives are very much affected by the bigotry and resentment generated when society fails to take these problems seriously. The comedians who don't care aren't going to change...but then, they themselves have no standing to whine about how they are being "oppressed" for their roles as comedians.
Now, you make a valid point about the slippery slope argument -- especially when you point out how Chris Rock's joke was fairly mild compared to what raunchier comedians spew. Jada may not have cared all that much about Chris taking a verbal jab at her; and, if she did, she has sure been publicly silent about it. And that's why it's ridiculous that people are commending/praising Will for his behavior -- if we let people slap comedians for offending them, where does it end? A punch? A kick in the groin? Homocide?
But, like with anything in life, the slippery slope works both ways. If we demand 100% artistic freedom -- and zero consequences -- for comedians when their targets feel their material crosses a line, where will it end? How egregious will the "court jesters'" insensitivity become? And will other public figures be demanding the same leeway? How long before entertainment pundits or civil servants argue: "Well, if comedians are allowed to say it, why can't *I* say it, too?"