“Where are we by the way?” Letterman asked his celebrity guest 10 minutes into their interview.
“We are on the outskirts of lovely Yellow Springs, Ohio,” Chappelle answered with a grin. The masked audience applauded and cheered with pride.
The footage for Letterman’s show was filmed during one of Chappelle’s outdoor comedy events this summer. Chappelle’s events, which have been referred to as “An Intimate Socially Distanced Affair," have included other guests such as Jon Stewart, Chris Rock, Tiffany Haddish, Jon Hamm, Michael Che, Erykah Badu, Michelle Wolf, Common, Donnell Rawlings, Talib Kweli, Cipha Sounds and Mo Amer, among others.
The Netflix special opens with Chappelle and Letterman hitting golf balls at the Young’s Jersey Dairy driving range. The episode bounces back and forth between Chappelle and Letterman exploring Yellow Springs while chatting, and the two on stage at Wirrig.
As Letterman asks questions about Chappelle’s decision to quit the Chappelle Show in 2006, Chappelle said the best part of the decision was “ending up here.”
“This is when I started to fully realize the value of being part of a community,” Chappelle said.
Born in Washington, D.C., and as the son of divorced parents, Chappelle grew up part of the time in D.C. and the rest of the time in Yellow Springs with his father. Chappelle’s father was a teacher at Antioch College, so Chappelle would spend many Christmas vacations in Yellow Springs, he said, and even attended middle school in town.
As the celebrity friends strolled down Xenia Avenue, Chappelle told Letterman “this place hasn’t changed in 100 years. It’s aesthetically almost identical. I remember walking and getting groceries here with my dad."
Dozens of shots of downtown Yellow Springs showed local storefronts, popular restaurants and pedestrians out for a walk. It appeared to be an ideal Yellow Springs day — sunny and blue-skied — when the episode was filmed.
“I think the charm of small-town life is your days are more predictable," Chappelle said. "The faces are more familiar. People know my name; I know their names. When you’re famous, everyone knows you. You don’t know anybody. But here, everybody is famous.”
On stage, the two touched on more serious topics like politics, Chappelle’s religious beliefs, and also Yellow Springs' historical background and involvement as an abolitionist town during times of slavery.
“My dad and some of his friends started a thing here called an African-American Culture Week,” Chappelle said. “Just something that would celebrate Black culture in small-town Ohio.”
In a segment in the middle of the episode, the two go on an adventure into Glen Helen as Chappelle explains the legacy of the town’s namesake, the Yellow Springs.
“We’re headed toward the body of water for which the town is named, is that correct?” Letterman asked.
“That’s right — The Yellow Springs," Chappelle said. ”People used to think it had all kinds of magical healing properties, and the local legend is, if you drink from the spring, you’ll always come back to this place."
“Have you ever drank anything out of the spring?” Letterman asked.
“Clearly, I have drank a lot,” Chappelle answered.
Letterman took a drink with his mouth from the spring, then as the two were leaving the watering hole, Letterman turned back around and dunked his entire head beneath the running water.
“You’re definitely coming back here,” Chappelle laughed.
“Not only coming back here, I’m buying property,” Letterman said.