Dave Chappelle playfully roasted Kanye West during a surprise comedy set at The Comedy Store in West Hollywood, California on Sunday night.

Surprise Performance and Audience Reaction

The 52-year-old comedian delivered a series of jokes before inviting the 48-year-old rapper to join him onstage in the venue's Original Room. Chappelle’s quip, “Kanye West has lost more money than I’ve ever made,” drew laughter and applause.

The crowd greeted West with high fives and a standing ovation as the duo exited the stage together. The Comedy Store also hosted surprise performances by comedians Shane Gillis, Louis CK, and Chris Rock, as announced on their Instagram page.

Longstanding Relationship and Upcoming Shows

West and Chappelle have a long history, dating back to the early 2000s when the rapper appeared in two episodes of Chappelle’s Show on Comedy Central in 2004 and the 2005 rockumentary Block Party.

Chappelle is preparing for his upcoming Netflix Is a Joke shows at the Hollywood Palladium, scheduled for Thursday, Friday, and Saturday. The event, titled Pulling Up, is advertised as a blend of comedy and music, sparking speculation about potential future collaborations with West.

West's Upcoming Performance and Chappelle's Controversies

Ye is scheduled to perform on May 23 at Jawaharlal Nehru Stadium in New Delhi, India, in support of his newly released 12th studio album, Bully.

Chappelle has faced criticism for his controversial comments, particularly regarding the transgender community. In a recent interview with NPR, he defended his decision to headline the Riyadh Comedy Festival in Saudi Arabia, stating, “The United States government does business with the Saudis. Netflix does business with the Saudis. And none of these things were an issue until I went there.”

He also addressed criticism of his jokes about transgender individuals, saying, “I did resent that the Republican Party ran on transgender jokes. You know, I felt like they were doing a weaponized version of what I was doing. That’s not what I was doing.” Chappelle refers to himself as “Team TERF” (trans-exclusionary radical feminist).