Chappelle memorably hosted SNLin 2016 after Donald Trump won that year’s election. During his opening monologue, he shared that he didn’t know Trump was going to win.

“I did suspect it,” he went on to say. “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.”

He then concluded the opening with, “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” — something he’d end up apologizing for the following year. “I was the first guy on TV to say, ‘Give Trump a chance.’ I f**ked up. I’m sorry,” he said at a Robin Hood benefit.

With his 2020 SNL hosting duties, he reflected on Trump’s time as president while speaking to the division rampant in the United States. He also hosted in 2022 following the midterm elections but faced criticism for that hosting appearance, where he talked about Kanye West, antisemitism and more.