Today, Netflix premiered two Dave Chappelle stand-up specials, Deep in the Heart of Texas and The Age of Spin, his first (and second) since 2004’s For What It’s Worth. The term “comeback” has been thrown around for the occasion, but factually and symbolically, it doesn’t really fit. Chappelle has been performing stand-up sets frequently over the years—including his 10-night residency at Radio City Music Hall in 2014—and became Black America’s straight-talking but compassionate uncle when he hosted the first Saturday Night Live following Donald Trump’s election, an episode that was punctuated by an 11 minute monologue that included raw, fresh material about our new president. (“It seemed liked Hillary was doing well in the polls, yet… I know the whites. You guys aren’t as full of surprises as you used to be.”)
There’s nary a comedian from this millennium whose jokes has achieved the combination of immediacy and ubiquity that Chappelle reached during the short reign of Chappelle’s Show. There’s a generation of young adults whose first reference to Rick James isn’t “Super Freak,” but Charlie Murphy kicking his chest in; Ja Rule’s credibility as a social commentator still hasn’t recovered; and African-American white supremacy now has a name (Clayton Bigsby). Chappellean humor is sharpened by social observation and serrated by absurdity, and his perspective should be even more potent in 2017.
But Chappelle has at least “returned” to the taped special format. He’s 40 pounds heavier and his voice’s twangy shrill has deepened into a rasp, but he still feels like something of a myth. To that end, we spoke to musicians, actors, and comedians who’ve worked with him, snuck into one of his shows, or have at least given him a fist bump about their memories of his personality and comedy. Read the conversations, condensed and edited for clarity, below.
When I first met Chappelle, it was because when I was working at Nkiru Books [in Brooklyn], we were dating the same girl. I met him in the hallway of this girl’s apartment, because she was kind of dealing with both of us and we overlapped a little bit. So I didn’t really like him: “Oh, that’s the guy that’s dating this girl.”Then I met him a couple of years later at a college in Ohio—whatever college was in his hometown. De La Soul was doing a show and I was in Cincinnati hanging with [producer] Hi-Tek. Chappelle was at the De La Soul show. The second time I met him, Half Baked had come out. I was like, “Yo, I’m a huge fan of Half Baked.” The next time I saw him, me and Hi-Tek was working on the Reflection Eternal album and I saw him walking down the street in the Village, and I invited him to come hang out in the studio. That’s when we became friends.My favorite Chappelle moment is probably Block Party. It was shot in a neighborhood that I spent a lot of time in as a youth running around in, so it was like a homecoming for me. It was revolutionary because he did it with his own money and everyone involved got paid—and still gets paid. It was revolutionary because he created something out of his heart and his soul and his brain. Dave thinks like a revolutionary: He’s a comedian, but he thinks in terms of this real hyper-independent, hyper-community way of thought that’s really admirable.When you go to the Smithsonian in the African-American museum part, I’m in there, Black Star is in there, Common’s in there, the Roots are in there, Jill Scott’s in there, Erykah [Badu]’s in there, Dave is in there. So when I go in there, I’m like, “This is a part of history.” My crew made history not just with Block Party, but is making history with what we’re doing. I like being a part of living history.
Maybe a year ago, we were working at Pabst Theatre in Milwaukee, and we had a pastry chef who asked us our dessert request. She was kind of annoying with it when I told her to make me an apple pie. She said, “Don, that’s pretty simple.” I said, “If it’s so simple, why don’t you make me an apple pie and put my name on top of the apple pie.” The next day I was excited. I walked to the end of the table where she had her pastries, I looked on the table, and there was an apple pie that had my name, “Donnell,” written on the top of it.
I was excited about it and wanted to share this moment with everyone. Dave came to work and I went to him with the pie behind my back and I showed it to him. I was like, Dave, I got my own pie. He said, “So what?” I was like, “But it’s a personalized pie.” Dave looked at me dead in my face, and said, “Donnell, you know it’s gonna take every muscle in my body for me not to stick my penis in your pie?”
And that’s when you judge your friends. He knew that I had to go on stage in the next 15 seconds and so he was taunting me. He was like, “Yo, can someone put that pie in the microwave for 15 seconds and make it nice and warm?” Then he was like, “You know how much value my penis would add to your apple pie?”
I’ve had some creative moments with Dave, but when you talk about testing the friendship, it’s the day that your friend looks you in the face and says he wants to put his penis in the middle of your name so the pie can go from “Donnell” to “done.”
Rawlings starred in Chappelle’s Show and has since gone on to appear on Guy Code, Adult Swim’s Black Dynamite, and Black Jesus.
I started out in Chicago and right around the height of Chappelle’s Show—he played the Congress Theater. It was 2004, I was 21, and I didn’t have whatever the tickets cost. I was trying to get into the show and tried going through the back saying, “Hey, I’m a comedian.” That didn’t work out.
I ended up going around to these different entrances and then there was a set of doors that were just open. I go in and there were these handful of seats just open. So I sit in these seats hoping that nobody claims them. I was nervous the whole time, but nobody ever approached me to leave. To go from sneaking into somebody’s show 13 years ago, to doing shows with them on a regular basis and being able to reach out and ask for advice, is crazy.
One time at Gramercy, I was drunk as fuck. I remember when I first started doing comedy, one of my friends had bootlegged the audio from Killin’ Them Softly off of Napster or something. So I was listening to that a lot and Dave had the bit where he’s in the car with his friend Chip—and Chip is drunk and says [to a cop], “Dave, I’m gonna race him.” [Then Chappelle says] “I knew it was a bad idea, but I was high. I tried to explain to him it was a bad idea, but all that came out was, ‘Well, nigga sometimes you gotta race. I don’t know.'” I remember just rewinding that bit all the time—just the delivery and the timing on that bit. I said [at Gramercy], “Befoooorrreee I go off, I wanna do my favorite Chappelle bit.” I butchered the bit, but that was one of my favorites.
Burress has been featured prominently on Broad City and the Eric Andre Show, and currently hosts the podcast Handsome Rambler. Comedy Camisado, his most recent stand-up special, premiered on Netflix on February 2016.