When Dave Chappelle Left Chappelle's Show He Made An Heroic Choice
A resurfaced 2005 interview shows how badly we misunderstood Dave
In 30 years of interviewing only one person has ever walked out on me. Like, I was in the midst of talking to them, the interview was not over, and they got up and left. Dave Chappelle.
He abruptly left our 2005 BET interview in Silver Springs, Ohio, but, to his credit, he did it smoothly and with a smile. I wasn’t even mad at him. I was pushing into territory he didn’t want to go into, asking why he abruptly walked off the set of Chappelle’s Show and abandoned the whole iconic thing. He was answering but you could tell this was hard stuff for him to talk about. He wanted to be real and he was but it was emotionally tricky for him to do it. And then, in the midst of getting a series of very real answers, one of the three cameramen shooting the interview said he had to stop to change the batteries in his camera. This is normal in a long interview, but he could have said this quietly, but I think he did not realize what an incredibly sensitive situation we were in. As soon as he said that, Chappelle eased up out of his chair and grabbed his coffee and politely said, “I’m going outside for a cigarette.” He never came back. But I did get an answer to the big question: what had happened to Dave?
Thank you to my friends at Paramount/Viacom for giving me permission to rerun parts of this 2005 interview because it’s important to see. When you see the key section toward the end you’ll understand the true reasons why Chappelle abandoned Chappelle’s Show. And you may agree that Chappelle made an heroic choice that put him way ahead of his time. I just recently reacquired this interview and rewatched it for the first time in 20 years and now, in the context of all that’s happened with Chappelle and a lot that’s happened in society, this interview looks a lot different than it did back then.
At the same time, I hope you’ll also see how you can work your way into asking someone about something they don’t really want to talk about. Being a journalist means sometimes asking questions that the subject doesn’t really want to answer. Journalists are very ‘I’m not one of your little friends.’ We’re supposed to ask tough questions or at least, we’re supposed to ask the most relevant and important questions whether or not you want to answer them. How did I get Chappelle to talk about the end of Chappelle’s Show when he didn’t really want to? Let’s talk about that, too.
Chappelle’s Show was a monster. It was insanely popular. So popular that after its 2nd season Comedy Central gave Chappelle $50 million to produce more. But months after signing that deal, as Chappelle was on set shooting the show, he heard someone on set laugh in the wrong way. That caused him to rethink everything and he walked off and never returned. At least, that’s what he has said. Many people dismissed him as crazy—they said, who would run away from $50 million? People laughed at him. A year later I talked to him for BET.
It was a half hour special to promote The Block Party but all I cared about was getting into why he left Chappelle’s Show. But I had to be careful. He didn’t want to talk about that. I had to be stealthy. Throughout our time together I crept slowly toward the topic. We started talking about the Block Party, his most recent project, the one he was there to promote. In time I shifted to discussing how brilliant Chappelle’s Show was. I wanted that topic to start in really a positive way.
I let him know how much I personally loved the show. It’s always great when you can give an artist a genuine compliment during an interview. To be able to say ‘Your album is so great,’ or ‘Your TV show is really engrossing,’ when you really believe that is powerful. It boosts the ego and it relaxes them. It makes them feel like they’re talking with someone who understands them. That makes them open up. I wanted to make Dave feel good about the conversation. Then, when I thought his ego had been sufficiently stroked, I quickly turned the corner. I asked why he left. I hate a long, pointless build up to a question which really communicates ‘I’m nervous to ask this.’ If you ask with conviction that alone helps suggest that they should answer. Don’t tell people that they don’t have to answer this if they don’t want to. They always have that option whether you say it or not. If you’re in media, act like they should answer our damn questions.
Also, I love short, direct questions. It feels more like a friend asking a friend when you can get into the topic swiftly.
Once I got into the question of why he left, after first establishing myself as one of the show’s fans, so I had more standing to ask than most reporters. This was personal for me. After that, he felt like he had to answer. I kept the convo flowing with short quick follow ups to keep us going deeper and deeper into the topic. These are natural follow-ups, things that come up as we’re talking, so we really stay in the moment.
We got to the heart of the matter near the end of our time. This is the all important last three minutes when we got into the reasons why he left. Watch this":
What he’s saying there is that he removed himself from an environment that he considered toxic. He prioritized his emotional needs—and his own mental health—over economic gain. He chose to center his needs over a corporation’s needs. He chose to listen to his spirit instead of following the carrots and the sticks of the company that was paying him. If this happened today, when we have a greater appreciation for work/life balance and the realities of mental health, he would be hailed as a hero. Instead, he was pilloried as a loon. But he was right.
Chappelle left the show not because he was crazy but because he was an extremely sane It’s heroic for him to turn away big money when his work life became too corrosive. Chappelle was, in 2005, talking about a lot of the things that Simone Biles and Naomi Osaka and millions of millennials are talking about now. He was ahead of his time and considered crazy but in truth he was really smart.
It's easy to call someone crazy for screwing up a multi-million dollar deal but what if they value sanity over money? That’s not crazy. There was a time when people thought he would never work again and now he’s one of the biggest stand ups in the world. He left one $50 million deal with Comedy Central and later got a Netflix deal that gives him $20 million for each stand up special he does. At a critical moment in his life he did what everyone told him not to do—he chose his sanity over generational wealth—and not only has he survived, Dave has thrived.