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Here Are Some of the Best Moments From the Night Dave Chappelle Won the Mark Twain Award

Morgan Freeman narrated the opening, and Chappelle smoked onstage

Photograph by Tracey Salazar courtesy the Kennedy Center.

Last night, Dave Chappelle was honored at the Kennedy Center and was presented the Mark Twain Prize for American Humor. Musicians like Common and John Legend and comedians like Tiffany Haddish and Jon Stewart all came together to honor their friend and colleague for his work. Here were some of the best moments from the evening.

The Duke Ellington School of the Arts marching band performed with Morgan Freeman

Melding Chappelle’s past and present, his alma mater’s marching band got to perform onstage with Morgan Freeman, who provided the opening narration for Dave’s recent specials. After the voice of God commanded the crowd to “go fucking crazy,” the high schoolers exploded onstage and into the aisles to open the show with Prince’s “Let’s Go Crazy.”

Morgan Freeman and Chris Tucker on the red carpet. Photograph by Tracey Salazar courtesy the Kennedy Center.

Lorne Michaels talked about how Chappelle helped the SNL cast heal after the 2016 election

Saturday Night Live creator and producer Lorne Michaels said he knew he had to have Chappelle host the show the week after the infamous election night. “Whichever way the election went, I knew I needed someone to explain what had just happened,” Michaels said.

“That Wednesday after the election when we had the readthrough for the show, the mood was pretty bleak. People were feeling tense and very vulnerable. It was a mess. I did my best to get it back on track, and then Dave sat down beside me at the head of the table, looked at everyone, and sensed the emotion in the room. He asked if he could read a quote by Toni Morrison. The quote read ‘This is precisely the time when artists go to work. There’s no time for despair, no place for self pity, no need for silence, no room for fear. We speak, we write, we do language. This is how civilizations heal.’ I knew then that it would be okay.”

Neal Brennan recounted his days working on Chappelle’s Show

Longtime writing partner and Chappelle’s Show co-creator Neal Brennan reminisced on his decades-long relationship with Chappelle, especially when working on their groundbreaking sketch series. “We went around pitching [a rough version of the Chappelle Show] to a few networks,” Brennan said. “HBO didn’t go great. The woman actually said to Dave, “Why do we need you when we have Chris Rock?” See, back then, there could only be one popular black comedian at a time, unlike today where there can be three.”

Though he’s proud of his work, Brennan said Chappelle’s Show was a grueling process. “It wasn’t fun at all, it was hard,” he said. “We had to stay awake for 48 hours at a time just to keep up with the schedule. We both had erectile dysfunction. I told Dave about mine, and he said, “It’s because we’re using laptops too much man, plus we’re not as young as we used to be.” Meanwhile, there’s no causal link between laptop use and erectile dysfunction, and also we were 29. Asking me and Dave if we’d want to do another TV show is like asking Jussie Smollett if he wants to grab a midnight footlong down at Subway.”

Colin Jost honored Mark Twain

After fellow SNL cast members Kenan Thompson and Michael Che thanked Chappelle for his comedic trailblazing, Colin Jost announced he was there “to celebrate Mark Twain.” “To me, that’s comedy,” he said. “You think Dave Chappelle’s funny, have you guys read the short story ‘The Prince and the Pauper’?” If you don’t believe that Mark Twain’s hilarious, I would just like to read a brief passage from “Huckleberry Finn.” “Huck Finn turned to his friend Jim, or as we called him,” you know, I don’t have to read the whole thing.”

Kenan Thompson, Michael Che, and Colin Jost at the awards. Photograph by Tracey Salazar courtesy the Kennedy Center.

Aziz Ansari shared how he and Chappelle did shrooms together

One night, after performing with him in Austin, Chappelle asked Ansari if he wanted to eat some psychedelic mushrooms with him. When Ansari said he was going to try to get some rest, Chappelle said, “Aziz, no one knows this, but tomorrow they’re going to announce that I am the winner of the Mark Twain Prize for American Humor. What are you going to tell your kids 20 years from now? Are you going to tell them, “I was there the day Dave Chappelle found out he won the Mark Twain award and we ate mushrooms together and we had the night of our lives,” or are you going to tell them you got some sleep?” The mushrooms were consumed.

Aziz Ansari on the red carpet. Photograph by Tracey Salazar courtesy the Kennedy Center.

Jon Stewart thanked Chappelle for ending Chappelle’s Show

Stewart was hosting the Daily Show when Chappelle got his big break with Comedy Central. “Chappelle’s Show was this rocket ship that [Chappelle] created, and it became this cultural phenomenon,” Stewart said. “Comedy Central would do anything to keep it going. They offered Dave 50 million dollars to give them just one more. But Dave at that moment was conflicted, because of how difficult the show was to do, because he wondered about its impact on the audience he meant it for, and he wondered if the creative process wasn’t right for it. And he walked away.”

“And it was that moment, that I remember thinking, “Comedy Central has 50 million dollars?” These motherfuckers won’t even let us have snacks. 50. Million. Dollars. Well, at that point, Dave, he left, he was done. But I knew that money was going to need a home. Dave, I want you to know tonight that I’ve raised that money like it was my own.”

Jon Stewart and Tracey McShane. Photograph by Tracey Salazar courtesy the Kennedy Center.

Dave Chappelle smoked on the Kennedy Center stage

True to Stewart’s assessment of him –“I don’t know anyone who cares more deeply and who gives less of a fuck”– Chappelle gave a gracious speech and smoked not one, but two cigarettes while accepting the award.

Speaking completely off the cuff, Chappelle said, “Standup comedy is an incredibly American genre. I don’t think any other country could produce this many comedians. And I don’t think there’s an opinion that exists in this country that is not represented in a comedy club by somebody. I know comics that are very racist, and I watch them onstage, and I think, “Mmm, that motherfucker means that shit.” I don’t get mad at them or hate them, we go upstairs and have a beer, and sometimes I even appreciate the artistry that they paint their racist opinions with. The First Amendment is first for a reason. Second Amendment is just in case the first one doesn’t work out.”

He also honored his mother for consistently supporting him and going to every one of his shows when he was starting out. “How many of you have ever heard your mother say, “Pussy jokes were a little too much tonight son”?”

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Jane Recker
Editorial Fellow