Dave Chappelle & Jon Stewart Talk Politics Unusual (Video)

As comedians, Jon Stewart and Dave Chappelle are inherently political. Both have led illustrious careers in their respective fields, utilizing humor to comment on and critique policies, politicians, social movements and more. As the anchor of Comedy Central’s Daily Show, Stewart brought high-brow, intricate political topics into everyday discourse. With Chappelle’s Show and his stand-up, Chappelle has used raucous comedy to make piercing statements about the American way of life. Now, in what could be called the “Trump Era,” Stewart and Chappelle still have a lot to say.

In an interview with 11-time Emmy Award-winning journalist Christiane Amanpour for CNN, Jon Stewart and Dave Chappelle discussed not only their joint comedy tour but also more pressing topics. In particular, Amanpour references a resurgence on things like “assault on free speech, the partitioning of the country along race and religious lines, the protests on the streets and in Congress,” and she asks her guests if they internalize all of those elements.

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“I think we always internalize what’s around us. We’re comedians,” says Stewart. He adds that he doesn’t necessarily believe there’s been any “resurgence” in the country being divided along racial and other lines. “I feel like that’s always with us. It’s just, at times, it’s bubbles up more explicitly. Even when you don’t say it out loud, it still exists. It’s always foundational,” he says.

Amanpour then turns to Chappelle, asking him if he thinks division is more acute in the current climate. “No, man, no,” he says. “Even when they say that Russia influenced the election, it’s kinda like ‘Is Russia making us racist?,'” he adds with a tone of incredulity in his voice. His point echoes Stewart’s earlier premise, that America has always been a deeply divided and racist country. It’s not Trump’s doing. In fact, as Chappelle puts it, “He’s not making the wave, he’s just surfing it.”

When asked if the Trump era makes the landscape more fertile for comedians, Chappelle shifts her question on its head. “I would not even name the era the ‘Trump Era,'” he retorts. “He’s getting too much credit…all he does is sing those people’s greatest hits,” he says of Trump’s followers. “‘Build a Wall,’ all these things we’ve heard before. He just sings all the songs. He’s the only one who’s been brash enough to do it.”

After calling Trump “a performer” near the 4:45 mark, Stewart goes on to say that Trump is “a salesman who changes his pitch depending on who he’s in front of. What he doesn’t realize is that it’s all being recorded.”

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Chappelle is once again asked to comment on his thoughts about Trump, particularly as they relate to his November 2016 gig hosting Saturday Night Live, just days after Trump won the election. Amanpour references his monologue, in which he said he was willing to give Trump a chance as president. “I think I said the right thing at the right time,” Chappelle says when asked if he’s still giving Trump that chance.

He continues, “We had to recalibrate and put things in perspective. I’m a Black American. These feelings that people felt right after the election, we’ve felt that many elections consecutively.” He adds that he thinks “to some degree, people overreacted” to his statement on SNL. “The alternative to giving him a chance was storming the streets and, if something good’s on television, we’re not doing that. Is he doing a good job? Am I happy with what he’s doing? No. It’s been very difficult to watch the last couple of years.”

Stewart chimes in then (7:08) to say he, too, was wrong about Trump. “It’s been harder than I think I thought it would be. There was a part of me that thought, when you get in that [White House] room and it’s nighttime and there’s no one around and Teddy Roosevelt and Abe Lincoln and everybody’s up on the walls and they’re staring at you, that that brings a certain cognitive weight to what you’re feeling…I think that, oddly enough, he transformed the White House and the White House wasn’t able to transform him.”

On Tuesday, November 6, Americans have the opportunity to transform Washington, D.C. and—perhaps—the White House, by voting in midterm elections.

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Elsewhere in the interview, the two comedians comment on two other comedians, namely Louis C.K. and Bill Cosby. Near the 17-minute mark, Chappelle says of the convicted icon, Cosby, “I didn’t defend him. I mourned the loss of a hero…seeing him get perp-walked at 81 was devastating for every Black comedian…all of my heroes are either murdered by a gun or registered sex offenders.”