Dave Chappelle’s Who Is Jack Johnson Pulls No Punches on Diddy, Israel and More

Dave Chappelle just dropped a new stand-up special on Netflix out of nowhere, and yeah, the title is not subtle: 'The Unstoppable...'. It is his eighth, it is streaming globally, and it is very much Chappelle going straight at the third rails people keep telling him not to touch.

The frame: a comedy set told through Jack Johnson

Chappelle builds the whole hour around Jack Johnson, the first Black world heavyweight boxing champ (1908–1915), a man nicknamed the Galveston Giant who became a lightning rod in the Jim Crow era. Johnson was not just winning fights; he was openly living however he wanted, dating white women, flaunting wealth, and infuriating a country that kept trying to find someone to knock him off. Chappelle flat-out calls Johnson the epitome of an 'unapologetic black man' and uses that defiance as the spine of the show, bouncing between early-20th-century racism and the modern stuff we pretend we are better at.

The jokes you know are coming (and the ones you probably don’t)

If you expected him to avoid the heat after the blowback to The Closer and The Dreamer, he does not. He revisits gender jokes, acknowledges the backlash, and argues the outrage is really about policing what artists are allowed to say. He folds that into a wider tour of American hypocrisy, online punishments, and celebrity implosions, all filtered through that Jack Johnson lens of: what happens when someone refuses to bow?

The Diddy segment

One of the splashiest chunks is his bit about Sean 'Diddy' Combs, from the federal raids to the whispers about excess. Chappelle leans into the absurdity and the rot of fame-as-industry, arguing the same machines that elevate stars love chewing them up once they get 'too big for their britches.' The laugh line people will repeat is this:

'But if you’re 55 and you got a thousand bottles of baby oil in the house, clearly you can’t stop, won’t stop. You’re committed to the lifestyle. He just used the wrong lube. I think if he used Crisco, he would have gotten away with it.'

He also points a finger at the decades-long silence that lets powerful people do whatever they want, then shrugs at the moral hangover that shows up once the cameras turn.

Saudi Arabia, free speech, and the guilt test

The most combustible section digs into his appearance at the Riyadh Comedy Festival and how, in his telling, he felt freer to speak there than he often does in the U.S. He invokes Jamal Khashoggi, the war in Gaza, and American culture wars to make a blunt point: he does not feel bad about taking that stage, and he is more interested in the double standards around who gets punished for saying what, and where. He even riffs on late-night TV dust-ups, arguing that forcing a host to pay penalties for beliefs he does not hold amounts to compelled speech, and caps it with: he would take Saudi money 'so I can say no over here.'

He adds, with a smirk, that his transgender material played better in Riyadh than it does stateside. Subtle? No. Designed to poke the bruise? Absolutely.

So, what actually ties it all together?

The throughline is defiance. Chappelle is fascinated by people who refuse to apologize their way out of controversy, whether that is a boxer in 1910 or a comedian in 2025. He is not trying to make peace; he is trying to make a point about power, risk, and who gets to speak without getting swarmed. The set jumps from century-old heavyweight bouts to today’s culture-war firestorms, but it keeps landing on the same idea: the cost of being 'too big' and too blunt in public.

It is messy, funny, provocative, and intentionally uncomfortable. In other words, it is a Dave Chappelle special. 'The Unstoppable...' is streaming now on Netflix.