..."In our country you can shoot and kill" a Black man, "but you'd better not hurt a gay person's feelings," says the stand-up comic, who is Black.

...In "The Closer," Chappelle describes a US rapper who "punched the LGBTQ community right in the AIDS," compares trans women to the use of Blackface, and jokes about threatening to kill a woman and stash her body in his car.

In a leaked memo, content chief Ted Sarandos wrote that "content on screen doesn't directly translate to real-world harm," and so the principle of free speech outweighs any offense taken -- including by its own employees.

CNN spoke with four trans comedians about what they think Chappelle got wrong in "The Closer." Some said they had considered Chappelle a comedy hero. But three of the comedians said that, by targeting trans people -- trans women, mostly -- and adopting the language of opponents of trans rights, his comedy has mutated into something meaner, more dated and less impactful. (CNN has reached out to a representative for Chappelle and is waiting to hear back.)

Chappelle has been lauded throughout his career for forcing difficult topics on unsuspecting audiences and highlighting the absurdity and omnipotence of anti-Black racism. But his jokes about trans people only reflect his own intolerance, said Mx. Dahlia Belle, a Portland-based standup.

..."A joke should only be as offensive as necessary and, if it has to offend, it needs to be funnier than it is offensive," she told CNN. "No one should come away from a joke more offended than they are entertained. That's what makes it a joke."

Nat Puff, a Seattle comedian and musician with a large TikTok following and viral videos that predate that platform, said what disappointed her most about Chappelle's statements was the apparent hypocrisy. She quoted an empathetic statement Chappelle once made about how calling people "crazy" is dismissive, that those people are "strong" and it's their environment that's "a little sick."

"[The quote] shows so much awareness and, like, respect that he just does not show for trans people, which is the heartbreaking thing about it," Puff told CNN. "Like, I feel like he has good intentions with what he's saying. He doesn't seem like a hateful person, unlike J.K. Rowling. But the thing is, he's saying hateful sh*t regardless, no matter what his intent is."

...Chappelle’s The Closer spends a lot of time (more than you’d think for a 48-year-old straight man) talking about the LGBTQ+ community. Chapelle’s last special Sticks & Stones was similarly controversial, with jokes (or “jokes,” depending on your perspective) about the LGBTQ+ community, abuse allegations against certain celebrities, and his defence of admitted (but unprosecuted) sex offender and comedian Louis C.K

...It’s such a shame that Chappelle’s standup in the last few years has come to this. In his early career, Danielle Fuentes Morgan, who teaches a course on African American comedy at Santa Clara University, says that he “punch[ed] up, to speak truth to power, to focus his ‘attacks’ on injustices and institutions with discernibly more power than he had.” Punching up or down is a concept usually discussed in the context of comedy. Punching up means criticizing and mocking a person, group of people, or institution with more power than you. Punching down is the reverse. In Chapelle’s case punching up would be white people, the police, the government for example, trans people decidedly belong to a group with less power than the cis-het millionaire. In The Closer, Chapelle acknowledges that he’s been accused of punching down, and wonders what the phrase means. As Morgan writes, “In teaching Chappelle, it’s become increasingly important to address how a person can be marginalized while also marginalizing others.”

I’ve written about the real world impact media has on minorities before, but comedians are a special case. Culturally, comedians have a bit of an outsider/underdog complex that many can’t shake, even when they become famous millionaires. There’s even a common joke that comedians are themselves a minority group. And so they think they can joke about anything, forgetting they have influence, especially in the era of mass-produced, mass-streamed Netflix stand-up comedy.