The last time most Americans heard what Dave Chappelle had to say about the state of politics in this country, it was just five days after the 2016 election. The comedian was hosting Saturday Night Live and at the end of his opening monologue, he said, “I’m wishing Donald Trump luck. And I’m going to give him a chance. And we, the historically disenfranchised, demand that he give us one, too.”
A little more than seven months into the Trump presidency, Stephen Colbert wanted to know on Wednesday night’s Late Show if Chappelle thinks he still deserves a chance or if he has “given him all the chances he’s going to get.”
“It’s not like I wanted to give him a chance that night,” Chappelle replied to laughs from the audience. “You know, listen, man, in the last six months, I think we’re all getting an education about the presidency.” He said he’s never heard people discussing “ethics” the way they do now. “He’s putting all this stuff on the forefront.”
“Well, nobody really talks about oxygen until someone’s got their hands around your throat,” Colbert replied, making his guest laugh.
After casually mentioning that he received an Emmy nomination for his SNL episode, Chappelle noted that at the beginning of the monologue he “contextualized” Trump’s election. “Because a lot of white Americans finally got a chance to see what an Election Night looks like for many black Americans every cycle.”
Onstage at SNL, just moments after Kate McKinnon’s Hillary Clinton had sung an emotional rendition of Leonard Cohen’s “Hallelujah,” Chappelle told viewers, “I didn’t know that Donald Trump was going to win the election.” But, he added, “I did suspect it. Seemed like Hillary was doing well in the polls and yet, I know the whites. You guys aren’t as full of surprises as you used to be.”
In a subsequent sketch later in the show, Chappelle and Chris Rock played two black men who were not quite as surprised as their liberal white friends as the votes came in on Election Night. “It might be a historic night, but just don’t forget it’s a big country,” he warned.
“The shock of it was just like, c’mon, man, this is how traction works. I think this speaks to how effective Obama’s presidency was,” Chappelle explained to Colbert on Wednesday night. “Donald Trump’s the other foot. Good foot, bad foot, good foot, bad foot.” On the bright side, Chappelle said he thinks Trump will “make a more informed and better voter.”
“We’ll figure it out, we’ll work it out,” he said. At this point, the worst he had to say about Trump was, “He’s a polarizing dude. He’s like a bad DJ at a good party.”
On the heels of his 16-night residency at Radio City Music Hall, Chappelle was reflective on 30 years in comedy that started when he was just 14 years old. “This is a heck of a business to survive that long, like, I really didn’t think I would make it that far,” he said, before correcting himself. “Actually, to be honest, I thought I would do much better than I did.”
When Colbert noted that America thought it had lost him for good when he quit his Comedy Central show at its peak, Chappelle said, “You know, it’s funny, the whole time nobody saw me, it wasn’t like I wasn’t doing anything. I existed, I was just not on the big stage. I was not under the hot lights.”
When he left Chappelle’s Show, he said he was “stressed” all the time and started working out nonstop to help manage his anxiety. “The fear of poverty is a treadmill,” he remarked. “That will keep you pushing.”