Between 2005 and 2007 Dave Chappelle was on the cusp of being one of the most successful comedians in America. Then just like that… he wasn’t. He became a figure of fun and it had nothing to do with his performances. For the most part, people considered Chappelle to be off the deep end and it was hard to prove otherwise. It appears that Chappelle may regret some decisions he made in the past, decisions that cost him around $50 million.
Now seven years later, Chappelle, looking drastically different than the comedian we’re use to seeing, appeared on ‘Letterman’ to discuss his life, career and choices he made. The ‘choice’ we’re talking about is walking away from Comedy Central’s $50 million contract to continue ‘Chappelle’s Show’. The rumors after Chappelle made that decision were all over the place – some said he went crazy, other’s said he couldn’t handle the pressure and my favorite is that Oprah and a secret society were behind it.
Chappelle doesn’t openly admit that he ‘regret’ leaving the show, but there’s every indication that he knows he made the wrong decision. Chappelle was on the path to being the most dominant comedian in the game. It’s highly unlikely that he recovers from this disaster, but we certainly don’t believe he can’t make a comeback.
Photo by Chad Buchanan/Getty Images