The comedian previously told CNN ahead of the rapper's wild White House visit that he's "not mad" at Kanye for endorsing Trump, but during a stand-up show in Ireland this week, he dove into the topic with a lot more thought and profanity. He even gave his fans a fascinating history lesson when he compared Kanye to African-American boxer Jack Johnson.
TooFab obtained exclusive audio from the Dublin show at the 3Arena, where Jon Stewart and Michelle Wolf were also present on stage for the portion of the event Chappelle called "Ask a Comedian." Someone in the crowd quickly shouted out, "What do you think of Kanye?"
"I gotta state my bias: I f--k with Kanye, he's like literally a friend of mine. I had a lot of thoughts and feelings, and as you can imagine I got asked a lot about what happened in the Oval Office," Chappelle said. "When Kanye put that Make America Great Again hat on, he was like, 'This is like my cape,' and I was saying to myself, 'N----r, just wear a cape!'"
"Honestly, all jokes aside, I felt like my friend is bipolar, and I felt like he was having a manic episode on television," he continued. "And I was initially angry that they paraded him in front of those cameras. Kanye thinks and says things as fast as he thinks 'em, without refining them before he says them."
"Kanye West wants the full amenities of being Kanye West. He's a rich person that happens to be black, and he wants the rights of every rich person. He's completely analogous and this has happened before," Chappelle said to set up his history lesson. "This motherf--ker is Jack Johnson."
Johnson became the first black world heavyweight boxing champion when he beat Tommy Burns for the title on July 4 in 1908 after following and taunting the white fighter around the world for two years. He then successfully defended the title against James J. Jeffries in 1910 in a match dubbed the "Fight of the Century." He held onto the titled until defeated in 1915, and insisted on only fighting white men for the first five years of his long reign as heavyweight champ.
Chappelle still managed to have his Irish audience in stitches while sharing a few anecdotes about the American historical figure, who he described as "a bad motherf--ker" for how he handled himself in and out of the ring during a time when racism was rampant.
"He won the heavyweight championship in a time when white fighters refused to fight black fighters, because they claimed it was beneath them," Chappelle said, noting that the fighter even left the fight with a white woman, which was particularly brave because interracial dating got black men killed back then.
"This motherf--ker was a complete social anomaly, that society couldn't say he was wrong, unless admitted that they were wrong. Jack Johnson's an American riddle. He only fought for his freedom, not everyone's freedom. And the question is: Is that fair? Should he have to think about everyone?" he asked, clearly drawing a parallel between the fighter and Kanye's puzzling behavior.
He concluded with a message to not take Kanye too seriously as a political thinker.
"I don't think [Kanye] forgot us. I trust him as a person of intent, I just think that this n----r is betting on the wrong horse," he said to laughter. "Lucky for me, I know him well enough to not take political advice from him. I'm keeping my Yeezys and I'm still buying the records, but when he's on CNN, n----r, I'm turning the channel."