Dave Chappelle, the provocative comedian and architect of Chappelle’s Show, is one of the biggest names in comedy. Now in arguably the most successful chapter of his life and career, he views himself as not just an entertainer -- but as a professional processor of events and experiences.

For more than 25 years, comedian Dave Chappelle has called the small village of Yellow Springs, Ohio, home. Amna Nawaz traveled there to meet with Chappelle and understand why he’s invested millions of dollars into this community,

Dave Chappelle said he publicly criticized Rep. Lauren Boebert during a 2023 performance in Washington after the Colorado Republican posted an Instagram photo with him that included a caption disparaging transgender people.

"If you have the opportunity like I did, to invest in your community, then it's one of the greatest investments I've ever made."

The comedian says Rep. Boebert instantly weaponized their impromptu photo by posting it with a caption about gender, drawing a line between his comedy and Republican policy.

'Chappelle's Show' ran on Comedy Central from 2003 to 2006

The comedian spoke about how the crowd reaction from fans in Saudi Arabia and how “time and circumstance” justified his

Every day seems to find a new way to make me feel older than dirt, and today we have the realization that July 2026 will mark 20 years since all-time great sketch comedy Chappelle's Show wrapped up its disjointed third season on Comedy Central,