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We can all agree the entertainment space is better since Dave Chappelle has reemerged within it. After Chappelle famously walked away from a $50 million contract in 2005 and seemingly disappeared off the face of the earth, he has reemerged in the past four years, and now it seems he’s just as in-demand as he ever was.
Tuesday, Chappelle will release two new specials on Netflix (which obtained the rights through a reported $60 million deal that includes a third special): “Deep in the Heart of Texas” and “The Age of Spin.” These were pulled from two Chappelle standup performances (Austin in 2015, L.A. in 2016). Ahead of the release, Chappelle spoke via phone with the New York Times.
The Q&A is fascinating. You can check it out here.
One of the most interesting parts pertains to Chappelle's Saturday Night Live monologue in the wake of the 2016 United States Presidential election. The monologue was widely lauded. Chappelle shared insight into his SNL hosting experience.
"At a certain point [on election night], we were all in the writers’ room, and as the night went on, and Trump was picking up these Electoral [College] votes, everyone stopped writing,” Chappelle said. “And then everyone was just staring at the TV. I saw people tear up sketches they were writing. They’d assumed Hillary was going to win. Now there was essentially no show on Saturday. It was like the wind got knocked out of the writers’ room. I was really worried.”
To nail the show, he channeled inspiration from Louis C.K.
“The best advice I got was from Louis C.K.,” Chappelle said. “I went to a comedy club Friday night [before the show] and saw him. And Louis told me: ‘[Forget] the rest of the show. The monologue is all that matters.’ I was stressed out all that day. But right before I went onstage, this calm just washed over me. Everything just felt right.”
Chappelle started doing standup again in 2013. So, why is he doing it again?
“I could quit my show, and that’s one kind of difficulty,” he said. “But quitting doing stand-up would be another. I’m sure everybody gets to a point where they run out of [stuff] to say, and they’ve got to take a knee and recharge and be introspective and live their life. But it’s hard to not ever come back to. Guys might walk away from it and close the door, but they don’t lock it behind. Eddie Murphy always entertains the possibility of doing it again. Even though he doesn’t do it, I’m sure he thinks about it all the time. It’s just one of those things where you’ll do it for 10 years, and then you’ll think about it for the next 30.”
Shouting out the greats (like Murphy) is a common theme in the interview. Chappelle shared a poignant reflection on the death of Prince—whom Chappelle famously parodied in his “Blouses” skit.
“It’s a hard thing to talk about,” Chappelle said. “I looked up to him like everybody did. I didn’t know him that well, but the times that we hung out were fun and very memorable and often funny. He was very generous with his advice, and he was very generous with his access. He let me see some of his process. He fostered a community among artists. He used to have these parties where we would go over to his house, and there would be all these musicians that I admired, and they’d just do these jam sessions in the basement. Everybody at the party was playing something. I think when he died there was the icon dying, but then there was this pillar in the community of people dying.”
Chappelle discussed achieving fame and how people looked at him—as opposed to how his audience looks at him now: like they get him.
“A lot of times when you’re a famous dude, you don’t really feel like a person is actually looking at you,” Chappelle said. “They’re looking at the phenomenon that you’ve become. Every once in a while, a person will engage with you, and you’ll be like, O.K., this person actually sees me. But I didn’t want the headache or the scrutiny. It was too much for me at that point. I felt like after I quit my show, the crowds could actually see me. The audience recalibrated with me. They listened to me again. And it was great.”
In the interview, Chappelle also addresses President Trump’s election, falling in love with comedy again, the Bill Cosby scandal, and much more. Give it a read here.