The 52-year-old comedian faced backlash for performing at the Riyadh Comedy Festival in the Middle Eastern country - which has faced criticism for its human rights record - earlier this year but stressed he had no regrets about the show.
"These motherf***ers act like because I did a comedy festival in Saudi Arabia I somehow betrayed my principles ...," he said in his new Netflix special Dave Chappelle: The Unstoppable.
"They said, 'well, Saudi Arabia killed a journalist' and rest in peace Jamal Khashoggi. I'm sorry that he got murdered in such a heinous fashion. And also, look bro, Israel's killed 240 journalists in the last three months so I didn't know y'all were still counting."
Chappelle said his jokes about the trans community went down "very well" with the audience in Saudi Arabia.
'"I've gotta tell you something - transgender jokes went over very well in Saudi Arabia," he said.
The comic cited Jimmy Kimmel's recent suspension from his talk show as symptomatic of how free speech had been limited in the United States as he reiterated his past statement that "it's easier to talk in Saudi Arabia for me than it is in America".
"I'll take money from Saudi Arabia any day just so I can say no over here. It feels good to be free," Chappelle said.
"And I know that the people in Saudi Arabia can't say all the things that I was allowed to say. But a deal's a deal, and the king said that I could say these things. So I looked at it like I was on a diplomatic mission: I've gotta bring p**** jokes to the Middle East."
Chappelle said the assassination of right-wing political activist Charlie Kirk in September further highlighted the perils of being outspoken in the US.
"This is another reason it's hard to talk in America, because if you talk for a living and see Charlie Kirk get murdered that way, I'm gonna be honest, I was shook," he said.
However, he rejected comparisons between Kirk and civil rights activist Martin Luther King - who was assassinated in 1968.
"(People were saying) Charlie Kirk is this generation's Martin Luther King. No, he's not. That's a reach," Chappelle said.
"They both got murdered in a terrible fashion, they both got shot in the neck, but that's about where those similarities end."
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