Chappelle and Rawlings served as the guests for the second episode of Stretch & Bobbito’s NPR podcast “What’s Good,” where the group discussed Chappelle’s seminal Comedy Central TV series Chappelle’s Show and his forthcoming Radio City residency with artists such as The Roots, Childish Gambino and Yasiin Bey.
In the very beginning of the conversation, Chappelle reveals that his favorite sketch from the show wasn’t one many would expect — “The Playa Haters’ Ball.” “I think that was the most fun I’ve ever had on a sketch,” Chappelle said. “That was the dope thing about working that show — you never knew when it was going to hit like that but it was so much fun,” Rawlings added.
From there, Chappelle talks about his appearance on Saturday Night Live following Donald Trump’s election win. “The main reason I did it is because Phife [Dawg] had passed away and Q-Tip had called and told me ‘this is our last Tribe record’, and then Lorne Michaels put a heavy pitch on me,” Chappelle said. “I was pretty sure Trump was gonna win. In hindsight, I’m managing that Lorne knew Trump was going to win because he was real adamant about me doing the first slot after the election…the night that Trump won the writer’s room at 30 Rock was the saddest place on earth.”
Then comes a guest appearance from Badu via phone-in, where she and Chappelle talk about curating his forthcoming residency. “A lot of it is organic but something like this can’t happen unless a lot of people put their ego aside,” Chappelle said. “I called people that I respect and admire and love and everybody came together…this will be my 30th anniversary, this is the way to do it.”
Check out the interview below.