It’s been more than ten years since the final regular episode of “Chappelle’s Show” aired. Dave Chappelle famously left his show during production of the third season in 2005. And while he’s talked about it over the years, even opening up to Oprah Winfrey about his reasons for leaving, it doesn’t seem to matter.
People are still fascinated by the notion that he would walk away from a deal worth millions of dollars. During his appearance on “Late Show,” Chappelle was once again asked by David Letterman about the whole thing.
“Are you tired of talking about it?” Letterman asked, after bringing it up. Chappelle said that he doesn’t talk about it, but then explained his perspective of things.
“Listen. Here it is,” he said. “Technically, I never quit. I’m seven years late for work.”
He walked off of his hit show months after signing a $50 million deal with Comedy Central for a third and fourth season. At the time, “Chappelle’s Show” was a juggernaut hit, with many of its comedy sketches becoming viral sensations in the early years of social media.
After he left the show, Chappelle wound up in Africa for two weeks, leading to wild speculation about why he’d left, including drug abuse, writer’s block, and a mental breakdown.
In February 2006, he sat down with Winfrey and told her that it was more about creative control, feeling exploited, and wanting an improved working environment. He also admitted to stress overload, and trust issues – especially after signing such a lucrative contract.
At that time, he was still talking about a willingness to return to the show, should his demands be met. Once he returned to the states, though, Chappelle continued with his stand-up comedy schedule, but he never returned to “Chappelle’s Show.” Ultimately, the truncated third season was compiled and released as a “Lost Season” of the show, with cast members Charlie Murphy and Donnell Rawlings taking over the host position between sketches from Chappelle.
When asked about regrets, he told Letterman, “I look at it like this. I’m at a restaurant with my wife. It’s a nice restaurant, we’re eating dinner. I look across the room, I say, ‘You see this guy over here, across the room? He has $100 million. And we’re eating the same entree.
“So okay, fine. I don’t have $50 million or whatever it was,” Chappelle continued. “But say I have $10 million in the bank. The difference in lifestyle is miniscule.”
Ultimately, though, Chappelle reaffirmed that it wasn’t about the money. “Money gives me choices,” he conceded. “So that’s not nothing. It’s something. I can choose where I want my kids to go to school. I can choose where I want to eat any given day. It’s not the end all, be all. There are other things in my life that I did not purchase with money that are very valuable.”
He did admit that he’d like to have the additional $40 million, though, joking, “I think I might be a happier person.”