Dave Chappelle was awarded the Mark Twain Prize in 2019, a testament to the decades he’s spent working as a creative and comedian. With Chappelle’s Show, he was responsible for introducing the world to characters such as Clayton Bixby, Tyrone Biggums, and Ashy Larry.

The TV show kept the laughs coming with Charlie Murphy’s “True Hollywood Stories” and Chappelle’s impersonations of celebrities like Prince and Lil Jon. It’s something he hasn’t taken for granted, and Chappelle still recalls the moment he knew the series was something major.

Dave Chappelle cut his show short

Dave Chappelle famously walked away from his deal with Comedy Central in 2005, but not before giving two seasons of Chappelle’s Show classics that are now part of pop culture history. Already a seasoned stand-up comedian and writer, he was 30 years old when the show was at its peak.

Leaving $50 million on the table, Chappelle later admitted to feeling stressed and like his integrity was being compromised. He chose not to renew his show for two more seasons, but that doesn’t mean he didn’t realize its impact.

Dave Chappelle overheard reactions to ‘Chappelle’s Show’ on a subway

Naomi Campbell visited Chappelle at his studio in Ohio to interview him for her vlog, No Filter With Naomi. The old friends discussed his career and family, and whether he knew that Chappelle’s Show was about to take off way back in 2003. He caught an inkling when the series had people buzzing about it on the train.

“I was riding the subway up to the production office, and the night before, the Rick James sketch had come on,” he said. Chappelle noted it felt like a scene from a movie where someone first hears their song on the radio.

“The whole way, all anybody on the car was talking about was my show. They didn’t know I was sitting there … And I was hearing them laughing, talking about the show that was on last night. I said, ‘Wow, that’s a big one.’ And the DVD for Chappelle’s Show came out that day,” he recalled.

Chappelle added that DVD sales were nearly 1 million on that first day and on that same day, his contract was up with the network. He realized several things in that moment as everything played out.

“My relationship with the network had changed. My relationship with the industry had changed. And my relationship with the fans had changed. I made something that people really, really liked, and that was a great feeling,” Chappelle said.

Chappelle still had negative feelings attached to the show

Because of how things soured with Comedy Channel, Chappelle never had the opportunity to bask in his show’s success and celebrate. He told Campbell that he didn’t get to enjoy it because of how things ended. But Chappelle is reflective about his career and believes it’s bigger than one show.

He has plans to do more work that goes beyond the scope of “writing a joke and taking it to market.” Chappelle has a handful of live shows scheduled for 2021, but fans can watch his specials and Chappelle’s Show on Netflix.

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