Dave Chappelle sat down with David Letterman on Tuesday and touched on his shocking exit from Chappelle’s Show in 2005, saying he’s just “seven years late for work.”

Dave Chappelle Returns To The Stage

Chappelle shocked the world when he abruptly left his hit show on Comedy Central in 2005. Chappelle had just signed a reported $50 million contract with the network, only to leave in the middle of Chappelle’s Show’s third season, and many speculated that he had a nervous breakdown. Following his disappearance from the industry, Chappelle has kept to himself, becoming known as somewhat of a recluse.

In 2013, Chappelle returned to the stage, headlining the Funny or Die Oddball Comedy & Curiosity Tour. This year, Chappelle is performing a string of sold-out stand-up shows at Radio City Music Hall in June, followed by shows with musicians the Roots, Janelle Monae, Erykah Badu, Busta Rhymes and DJ Premier.

On Tuesday, June 10, Chappelle sat down with Letterman on the Late Show with David Letterman to announce a newly added show at Radio City featuring Nas, and spoke about Chappelle’s Show and his 10 years out of the spotlight.

Dave Chappelle: "Technically, I never quit."

Letterman wasted no time in asking Chapelle about what happened in 2005 and how exactly Chappelle left the show.

“Listen, here it is. Technically, I never quit. I am seven years late for work,” Chappelle told Letterman.

Letterman continued to press Chappelle, asking him if he regretted walking away from a $50 million payday. Chappelle admitted that his decision to actively refuse millions of dollars was confounding to most people: “There’s not too many people that don’t think I’m crazy.”

Chappelle went on to joke that there’s no extreme difference in his $10 million lifestyle and his $50 million lifestyle, saying, “The difference in lifestyle is minuscule. The only difference between having 10 million dollars and 50 million dollars – is an astounding 40 million dollars. Of course, I would like to have that money.”

Though Chappelle refused to get into specifics, he did tell Letterman that he left the show because he felt it was what he had to do.

“There’s nothing anyone can say. It’s just, you do what you feel like you need to do,” Chappelle admitted.

When asked how he felt about his decision now, Chappelle again remained vague. What he did say was that he looks at his decision with the perspective of a man who knows that money can’t buy everything.

“Money is the fuel for choices. Money gives me choices, so that’s not nothing. It’s something. I can choose where I want my children to go to school. I can choose what I want to eat any given day, but 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,”

“That’s right. And, let’s just say you had the 40 million, who’s to say you would be a happier or better person?” Letterman replied.

“I think I might be a happier person,” Chappelle deadpanned.

Article by Olivia Truffaut-Wong

Olivia Truffaut-Wong was born and raised in Berkeley, California, where she developed her love of all things entertainment. After moving to New York City to earn her degree in Film Studies, she stayed on the East Coast to follow her passion and become an entertainment writer. She lives on a diet of television, movies and food.