Being a fan of Chappelle, someone who can identify with quite a bit of his thinking, this is my takeaway from The Bird Revelation, when it comes to him bringing up “Pimp” by Iceberg Slim to explain his Departure from Comedy Central.
For Comedy Central, essentially, yes – Chappelle was their bottom b—-. One who reached the end of his mileage for he felt he was no longer in on the joke. However, rather than them setting him up to trap him, they instead used the name recognition for a season without Chappelle and, based off his feelings on Key and Peele, Mind of Mencia, and Amy Schumer’s show, arguably that is how they extended his mileage. All the while, arguably, they kept him trapped by being part of this narrative of him being some crazy negro who walked away from 50 million. Which, in the words of Wendy Williams: “When you tell people—particularly white people—that they can keep their money, […] because you muthafuckas think that we’re all slaves to somebody, white people, people in general, almost lose their minds.” And so, while they perhaps did not blackball or blacklisted him, there is a chance they made it hard for him to bounce back after all was said and done. Like a pimp who uglies up a ho to make it so no one else would want them. Much less, it would be hard for them to survive without the pimp. Hence him also noting the part on how to break a strong-willed ho, You had to beat the hell out of them. Which, perhaps, he felt Comedy Central was trying to do to him. Perhaps w/ that 50 mill. Alongside the idea of we made you famous and we can make you unfamous, if not infamous. Something I believe Chappelle talked about in Inside the Actor’s Studio or in another interview.