Letterman questioned Chappelle on why he left Chappelle’s Show and revealed that by doing so, the comedian gave up around $40 million. When asked if he regretted his decision, Chappelle candidly responded, “It’s very hard to go through something like this because no one’s really done it before. There’s not too many people who don’t think I’m crazy, right?”
The lifetime jokester was sure to get in number of laughs throughout the interview and ended with saying, “Sometimes I listen to a Jay Z record and it starts to make me feel bad about some of the choices I made. This guy’s had more fun in two songs than I’ve had in the last 11 years.” Watch it up top.