Richard Pryor was early to mid 80s, not 90s-00s; and certainly you couldn't do the same material today. Without doing a deep dive IASIP is very different in many ways to Pryor's and Chapelle's material - tone, content, format, delivery, context... in almost every way.

What also a lot of people don't want to countenance is that Pryor and Chapplle are African-American, McElhenney and Howerton are not. Who are the edgy black american comedians that are being "cancelled" today? And more crucially - some of the issues that formed Pryors stand up - ghettos, brothels and kids drug use - are much less prevalent today

Pryor's first special was released by the same publisher as Hard Days Night by the Beatles (MPI), so absolutely there was money involved there.

Chappelle's first TV appearance was on Def Comedy Jam, owned by $100MM record company Def Jam (it would sell for 150 mil a few years later - so that's a guess but I think a fair one)