Ben Thompson’s Stratechery has a nice article about Dave Chappelle. Go read it, and watch the embedded instagram video from Dave’s profile. As an unrelated aside, Dave is one hell of a story teller even when he’s not trying to be funny. I watched all 18 minutes and I was fully engaged despite there being only a few chuckles.
Based on watching the video and knowing that Dave is doing just fine with his current Netflix deals I would give Dave the following advice.
Ignore Sunk Costs: You feel you signed a bad contract and you quit the show. You’ve paid the price with an exile from the industry, whether that was self imposed or not. The fact of the matter is you can not change the past. Comedy Central has zero incentive to work with you in the future unless it would be a net positive outcome for them, and that seems unlikely given you are working with Netflix. It’s time to move on from this.
Appreciate the Business Side: In my experience many artists struggle with understanding the business world. Of course Comedy Central would want as much of the upside as possible when they underwrote the risk to get the show off the ground.
Don’t Expect The Average Joe To Care: In a world where piracy and counterfeits run rampant, it’s a big ask to your fans to get them to abstain from watching The Chappelle Show on streaming platforms. The entire youtube platform was built on the fact that consumers just want to watch, they don’t care who gets paid.
Think of the Benefits: Dave makes $20 million per comedy special on Netflix. Without the notoriety he received from The Chappelle Show it’s unlikely he is as popular as he is without the show.
Don’t Let Them Beat You Twice: It’s disconcerting to hear that Dave was completely clean of drugs, alcohol, and cigarettes at the time of the Chappelle show and to watch him chain smoke while he performs.
Update: It seems Dave won concessions from Time Warner and he’s now being compensated in some way. I hope to learn if he had to give anything up to get that.