Earlier this week, Dave Chappelle stopped by the Late Show with David Letterman to promote his upcoming residency at Radio City Music Hall. During the interview, he opened up about his life since walking away from his acclaimed sketch comedy series Chappelle’s Show. With his trademark bluntness and some healthy self-deprecation, Chappelle discussed how he had decided to leave the show to spend more time with his family, his thoughts on leaving a $50 million contract on the table, and how he thoroughly loves his new freedom.
On Friday night, Chapelle made another late-night appearance, dropping by The Tonight Show for a chat with host Jimmy Fallon. This time around, the interview was much more light-hearted as he reminisced of his past encounters with a variety of musicians, including The Roots, Prince, and Kanye West.
Discussing Prince’s usage of Chappelle on the cover for “Breakfast Can Wait”, Chappelle said: “That’s a Prince judo move. What am I gonna do? Sue him for using a picture of me dressed up as him? That’s checkmate.”
As for Kanye, Chappelle shared memories of the first time he met the rapper, specifically the phone call Kanye received while backstage. “I’m at the edit for the Chappelle’s Show watching sketches no one has seen before … because my life is dope and I do dope shit,” Chappelle recounted Kanye as saying.
Watch the full interview below:
Chappelle will be back in New York next week for his first NYC comedy shows in over a decade. The residency will take place June 18th through 26th at Radio City Music Hall and features the likes of Nas, The Roots, Busta Rhymes, Janelle Monáe, and Erykah Badu.