In 2005, Dave Chappelle famously walked away from his successful Comedy Central series Chappelle’s Show after only two seasons. A third season had been planned for that year, which would’ve earned Chappelle a reported $50 million if he’d decided to stick around. The following year, Comedy Central aired what they called the Lost Episodes of Chappelle’s Show, featuring some of the material Chappelle was working on prior to his departure. Cast members Donnell Rawlings and Charlie Murphy introduced the sketches in Chappelle’s place, and the abbreviated season consisted of just three episodes. 

Rumors began to spread that Chappelle had gone crazy or gotten hooked on drugs. In actuality, he just felt like he needed a break. Chappelle later told Oprah Winfrey that some of the sketches he was doing on his show made him feel “socially irresponsible.” A blackface segment that ended up airing as part of the Lost Episodes package made him particularly uncomfortable, and he began to worry that viewers were getting the wrong idea about his intentions.

Dave Chappelle Is Teasing a Comeback to the Era That Made Him

When Winfrey asked Chappelle if he’d ever return to Chappelle’s Show during that same 2006 interview, he said that he was still on the fence about it. However, Chappelle revealed that he wouldn’t be concerned with money should he decide to give it another shot. In his ideal scenario, half of the revenue he’d receive would go to charity. That way, even if he did something socially irresponsible, the proceeds could be given to a socially responsible cause.

But it would appear that Chappelle’s attitude has changed as time has gone on. In a recent interview with the Associated Press, the prospect of revisiting his beloved sketch comedy series after all these years came up once again. “If you’d asked me that question a year ago, I’d have told you absolutely not,” the comedian explained. “But in the last few weeks…I’m considering it.” It’s unclear where the potential revival series would land, though Chappelle did point out the fact that the comedy landscape has significantly shifted since the show originally aired, hinting at the possibility that a digital platform might be the place for it.