Back in 2006, there was no comedy show on TV more successful that “Chappelle’s Show”, boasting critical acclaim and record-setting DVD sales by tackling issues relating to race in ways both bitingly truthful and utterly hilarious.

Yet comedian Dave Chappelle’s sketch-comedy series abruptly ended when Chappelle himself pulled the plug, walking away from a deal that would reportedly have brought him $50 million.

During his sit-down with David Letterman in the new season of Netflix’s “My Next Guest Needs No Introduction”, Chappelle revisits his decision to walk away from such serious money.

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According to Chappelle, they were in the midst of filming a sketch in which race was at the forefront. It wasn’t until a member of the crew laughed at the wrong moment that Chappelle began wondering if everyone was getting what he was trying to do.

“It just raised an interesting question to me, which I was already wrestling with in the first place,” he told Letterman.

“The sketch wasn’t that bad. It’s actually funny,” Chappelle explained. “It was a pixie. It was me dressed in blackface who’d pop up anytime a person felt the pains of racism, which is a tough trick to pull off. It’s not a bad sketch, but hearing the wrong laugh, while you’re dressed that way, it makes you feel shame.”

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Meanwhile, his standup comedy tours had become far larger than he’d been used to, taking on the aura of a political rally or a rock concert. This, he told Letterman, left him feeling “bigger than [he] was comfortable with.”

Chappelle also admitted to being uncomfortable with the whole notion of celebrity, and explained the difference between celebrity and fame.

“Celebrity’s a role,” he said. “My I don’t like being a celebrity, but I like being famous.”

The new season of David Letterman’s “My Next Guest Needs No Introduction” is currently streaming.

Check out some Twitter reaction to the interview.