It wasn’t like I made a deal and had to go out and do a lot. [Laughs] I just had to deliver the shows.
And you’ll be releasing another brand-new special for Netflix this year as part of the three-special deal.
Yeah. I’m working on that now.
Not a bad deal. Do you have other unreleased shows still in the vault?
I have hundreds of hours of high-quality audio recording of shows I did after I quit my television show. And then I [taped] three specials — one in Chicago, one in Austin, and one in L.A. Oh, and I also recorded the Radio City shows.
These specials showcase a comedian who is reinvigorated by stand-up comedy.
I could quit my show, and that’s one kind of difficulty. 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.
Many of your contemporaries are still performing.
It kind of reminds me of the ’90s: Chris [Rock] is back out there, I see Jerry [Seinfeld] around, I hear Jon Stewart is around again. All these people who are great comics that stopped doing stand-up. It’s fun to see everybody back. It’s a good time for comedy in that respect. But the whole Trump thing makes it harder for comedians.
He’s so skewed, it’s hard to find an angle that sounds fresh. If you talk about him, it’s almost like you’re part of the chorus and not a soloist.
How do you view the dynamic between comedy and bringing truth to power?
I think it’s interesting that people perceive us as having a sanctuary. Because I don’t. In fact, I think we’re almost disproportionately taken to task over what we say.
“Chappelle’s Show” brought you a level of ubiquity few comedians ever achieve.
A lot of times when you’re a famous dude, you don’t really feel like a person is actually looking at you. 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. I started playing clubs again just because I enjoyed it. It was reaffirming a love for [stand-up]. It was important for me to do that. I needed that. I loved it. In the last few years, I’ve found an altitude I’m comfortable with.
You famously parodied Prince on your TV show. How did you react when you learned of his passing?
It’s a hard thing to talk about. 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.
Take me through hosting “Saturday Night Live” last November in the immediate wake of the election.
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. 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.
And yet you delivered a humorous, poignant monologue reflecting your equal parts hope and fear for the future.
The best advice I got was from Louis C.K. 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.
As someone who idolized Bill Cosby as a child, it’s surprising you dedicate so much time in both specials to the rape allegations against him.
The Bill Cosby thing was tough for me. I’m not saying that to detract from his alleged victims at all. But he was a hero of mine.
Is there a mourning process involved?
So many bad things happened to our heroes: Muhammad Ali had Parkinson’s; Richard Pryor had M.S.; Prince died too young. And Bill just looked like one of the guys who was going to get to the finish line and just die of old age. And this happened. Jesus Christ. It’s awful.
How do you respond when critics put you in the same conversation as comedy greats like George Carlin, Richard Pryor, Eddie Murphy and Chris Rock?
I appreciate it, but it’s not a useful thing. I don’t know what to do with that but just be humbled by it. You never feel like you’re better than your heroes.
What does life look like moving forward?
I need time to think. I need to have experiences. I have to live in order to get onstage. When I’m sitting there staring into space, that’s the heavy lifting. I’m like everybody: Sometimes I’m wildly optimistic; sometimes I feel doom and gloom. We all just keep moving.
Correction: March 17, 2017