September to October, 2004
On September 18, Chappelle signs a deal for $55 million, plus half of all the revenue from DVD sales, which might have pushed the deal into nine figures. He tells Entertainment Weekly, "What this money really purchased me was a certain peace of mind. It was an affirmation, just to be confident in your intuition.'' In October, Comedy Central announces that Chappelle's Show: Season One: Uncensored has sold more DVD's than any television show in history, topping The Simpsons. But Chappelle and show co-creator Neal Brennan are at odds and drifting further apart. Brennan would later say that Comedy Central "poisoned" their relationship by separating the two and negotiating with Chappelle first.