There’s a meme that has been around for a long time now which goes something like this: Tragically, the worst person you know just made a good point. That’s sort of how it feels to be writing a post highlighting a conversation between Jon Stewart and Steven Colbert, two progressives who are not exactly beloved figures on the right.

And yet, I think what Stewart said here genuinely is correct and it’s worth noting even if I’m not sure he really believes it. He stood up for free expression when it would have been a lot less messy to just denounce the bad people.

The conversation started as a discussion of anti-Semitism and the recent incidents involving Kanye West (“when I wake up I’m going death con 3 On JEWISH PEOPLE”) and Kyrie Irving (posted a link to an anti-Semitic movie). It started out exactly as you’d imagine it would with Colbert saying he’d called Stewart after the election to share his surprise that “fascism” wasn’t rising as quickly as they’d both feared. But then Colbert added, “Gotta say though, not great to see a lot of, sort of, updrafting of some casual anti-Semitism.”

This was a set up for Stewart (who is Jewish) to weigh in on several recent controversies. At first Stewart cracked jokes, saying that when he saw “the Jews” trending on Twitter he knew it wouldn’t turn out to be positive. “As our spokesjew…” Stewart said to laughter. He then went into a satirical rant about how Jews collectively wield power over the world. “I don’t know who ended Kanye’s Adidas deal, that wasn’t my committee,” he joked. “I’m on oil prices and bagel flavors,” he added.

“In terms of controlling, obviously, the world. Sorry,” he said to more laughter.

After a couple minutes of mocking some anti-Semitic tropes, Colbert interrupted to say Stewart was “very generous.” In other words, he’s making jokes instead of just using his platform to condemn people. And that’s when the conversation got a bit more serious as Stewart described getting outraged calls from people about Dave Chappelle’s appearance on SNL.

“Everybody calls me like, ‘You see Dave on “SNL”?’ And I say yes, we’re very good friends. I always watch and send nice texts,” Stewart began. “‘He normalized antisemitism with the monologue.’ I don’t know if you’ve been on comment sections on most news articles, but it’s pretty normal. It’s incredibly normal. But the one thing I will say is I don’t believe that censorship and penalties are the way to end antisemitism or to gain understanding. I don’t believe in that. It’s the wrong way for us to approach it.”

Stewart went on to say, “Penalizing somebody for having a thought I don’t think is the way to change their minds or gain understanding.” “Look, people think this. People think Jews control Hollywood. People think Jews control the banks. And to pretend that they don’t and to not deal with it in a straight-forward manner, we will never gain any kind of understanding with each other.”

This was an opportunity for Colbert to jump back in. “People have the right to say whatever they want,” he said. “So what is the response?” he asked.

Stewart argued that calling everything “anti-Semtism” was reductive and Colbert interjected that even if it was with a “comedic intention” Chappelle seemed to be engaging in anti-Semitic tropes.

“Comedy is reductive,” Stewart replied. He continued, “We play with tropes because everyone has prejudice in their lives and in the way that they view things. Comics rely on those prejudices as a shorthand for our material. Even the wokest of comics plays with tropes to a certain extent.”

Stewart quoted Kanye West saying “Hurt people hurt people.” He added that the only way to heal that hurt was to talk about it. “I’m afraid that the general tenor of conversation in this country is cover it up, bury it, put it to the outskirts and don’t deal with it.” “If you’re not allowed to say it…You know Dave said something in the SNL monologue that I thought was constructive, which he says, ‘It shouldn’t be this hard to talk about things,'” he added.

And here’s where I thought Stewart said something genuinely insightful. “Here’s the deal. We have our own tropes like ‘A white person’s success is because of privilege. A minority’s success is empowerment. A Jews success that’s a conspiracy.’ You feel that. I feel that but I have to be able to express that to people. If I can’t say that’s bulls**t and explain why then where do we go?”

I think Stewart is saying that Jewish people have their own tropes about what it feels like to be Jewish, i.e. the feeling that they are somehow suspect especially if the succeed. That maybe they got help from other Jews. And he’s saying that it’s something that has to be on the table for conversation rather than just refusing to discuss it at all. “If we all just shut it down then we retreat to our little corners of misinformation and it metastasizes. And the whole point of this is to not let it metastasize,” he said.

There’s an underlying premise here that I think is basically correct: That every group has its own prejudices and tropes and feelings about certain topics that we’re increasingly not allowed to talk about. He doesn’t use the phrase “cancel culture” but that’s really what he’s talking about. He’s saying that’s the wrong approach, that we need to try to understand where other people are coming from even if we think they’re wrong. It’s basically an endorsement of free expression over cancel culture.

The problem is that I’m not sure Jon Stewart really believes it. Stewart has a show called The Problem with Jon Stewart and earlier this year he did an episode titled “The Problem with White People.” He invited Andrew Sullivan on to give a voice to the other side, i.e. someone speaking against critical race theory and woke identity politics. In theory, this could have been a perfect example of what he’s describing, i.e. a chance to actually discuss a difficult topic while trying to understand different perspectives and where they are coming from. Instead it turned into a struggle session. Here’s what Sullivan wrote about it afterwards.

The point of the session was not to discuss anything, but to further enforce the dogma he had pronounced. So I found myself in the equivalent of one of those workplace indoctrination seminars — in which any disagreement is regarded as a form of “hate” or “ignorance.” But worse: I was in a struggle session with a live mob sitting in, cheering and jeering, which Stewart led and orchestrated. For good measure, Stewart called me a racist and told me I was not “living in the same fucking country as we are,” and went on to angrily call me a “motherfucker.”

I’m a big boy, and smiled through these assaults, but it does strike me as astounding that someone who once insisted that he believed in good-faith debates and not circus-like theater, someone who postured as open-minded, and disdainful of silly political grandstanding, behaved this unprofessionally. Stewart’s show made the old Carlson-Begala Crossfire seem like a model of substantive and elevated debate.

So, again, I think Jon Stewart said the right things. He’s standing up for free expression in this clip when it would have been easier not to and just go along with condemning the people who say bad things. Unfortunately, when it comes to running his own show, he’d rather give the mob what it demands.

After 12 minutes of jokes and discussion, Stewart asked Colbert if he agreed. “I don’t disagree with you John, I just wanted to say that I condemn anti-Semitism in all of its forms and I stand with all of my friends in the Jewish community…a counterpoint.” He’s literally saying exactly what’s expected of him as a progressive in good standing but he’s doing it a bit satirically as if to say here’s the ass-covering thing I’m supposed to say to avoid getting in trouble. It’s actually hard to tell if he’s really doing it to cover himself or if he’s mocking the idea that he should have to intone the words to gain absolution from the mob. It made me think that comedy could actually be funny again if people, including both of these guys, weren’t genuinely afraid of the mob.