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.
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.
Maybe it was 2011 and I was a server at the Soho Grand Hotel in New York. He walked in and sat down for breakfast, and I was like, “What?” Then I was like, “No. That’s not Dave Chappelle.” But I went to the computer and his name came up. He was in my section, so I had to talk to him anyways. So I was like, “Let me not be a dork.” I was a huge Chappelle fangirl and loved Chappelle’s Show.
I go over and introduce myself, and I’m trying to be a normal server. Then he asked me what I did for some reason. “What do you do?” Comedy. “What kind of comedy?” Sketch and improv. “What?” Another server took his breakfast order and put it in for me, and I sat and talked with Dave Chappelle for like a half an hour. I was in a daze because that was the coolest shit ever.
At the time, I was at this improv theater I had finished classes at, and they’d just kicked me off the house team—which is the team that the school curates with performers. They fired me and they didn’t tell me why, so I was in my feelings about it. I was just telling him how I felt like I didn’t how I could find my way in comedy without theater. At the time, you being at an improv theaters was everything, allegedly—that’s how you book TV shows. He was just like, “Don’t worry about that. You don’t need some theater.” He was also saying don’t worry about Saturday Night Live either: “I did not get on to SNL and ended up in a way better situation.” He was just giving me really kind advice.
I think my favorite joke of his is from Killin’ Them Soflty and he’s talking about the baby on the street. He’s like, “Baby! What you doing outside?” Everything about that bit is so perfect. It’s really funny but it’s also social commentary, because it’s so true of the hood. I came up in Philly in public housing and I wasn’t allowed outside. I wasn’t the baby out late, but there were tons of kids who were just outside at night, and there were liquor stores and check cashing places. If you went out of the way in West Philly, you’re on UPenn’s campus and it looked like you were in another city. That joke was perfect.
Long has appeared on HBO’s High Maintenance and CW’s Crazy Ex-Girlfriend.
A few people and I were invited to an after party [during Chappelle’s Radio City residency]. Marlon Wayans was there, Chris Rock was there, Hannibal, of course. It was crazy—it’s one of those things where you end up in a room and you’re like, “How do I not freak out right now?” Every awesome person is there just chilling.
Dave had performed. People were kind of in Dave’s face and he’s not super into it, but he’s chilling and trying to have a good time. But I’m not gonna leave this room without saying something to him. So at the very end of it, I just walk up to him to just kind of give him a fist bump. I don’t know if I said words to him or not, but he was very much in that moment not trying to engage with somebody who he didn’t know. It wasn’t malicious, but that’s why I hesitate to say “I met him.”
With me, there’s a couple of collectives of artists were I feel like everything I do is me auditioning for them and trying to be down with that aesthetic. That Dave Chappelle’s Block Party collective of artists, I’ve always wanted to belong to that. That work, that presentation, has met so much to me.
I think the most impactful thing that I revisit most is the Killin’ Them Softly special. It’s just iconic to me—things like the drug-dealing baby and a lot of the Clinton stuff that was going on at the time. It’s funny when you think about how long ago that stuff was and it’s still the kind of comedy record that I can put on in a tour van. People who’ve heard it a million times are laughing, and people who’ve never heard it are laughing.
Open Mike Eagle is a rapper who also co-hosts the New Negroes comedy show. His latest album, Hella Personal Film Festival, dropped last March.
The last time I met him was at my birthday party. I had to throw a party at this lounge in LA. I had all these people come, and Chappelle shows up to do a set. Imagine everyone else excited to see him but me—this is supposed to be my birthday. Everybody’s like “Oh my God. Chappelle’s here,” and I’m just back there sweating and talking to Donnell like, “Could you get him off?” But it ended up being one of the funniest nights ever. He stayed and hosted the party. The next day everybody was calling me and was like, “Yo, did you bring in Chappelle?” I’m like, “Yeah. Yeah I did. It was all me.”
You remember the [Trading Spouses] sketch [from Chappelle’s Show], where they swapped the husbands? Washington is just a funny character, man.
To put this old school, mean black father in a suburban white home, talking crazy, that was amazing. “G-G-G-Get yo ass in the car.”
Lil Rel Howery stars in NBC’s the Carmichael Show and played the heroic TSA agent in Get Out.
I’ve met him, but to say we’re friends would be an overstatement. I have seen him in the green room in a couple shows around L.A. and New York, where I was on the bill and he did a drop-in set or whatever. He’s got a cool vibe about him. He’s definitely a comic’s comic, in that regard.
He’s a comedian that all comedians respect. And more importantly, when he’s in the presence of other comics, I don’t feel like he carries himself with an air of superiority. There’s a humility about him that isn’t mentioned too often, or that gets lost in the shadow of all the other things that are so dope about him. You definitely feel cool being around him.
There’s a line in Blue Streak that still makes me laugh. He’s Martin Lawrence’s accomplice, and Chappelle says to the bad guy, “I’ll rip your tongue out and lick my balls with it.” It’s one of the silliest and coldest fuckin’ movie lines. It doesn’t matter the time of day, what, when, where: I will laugh hilariously at that.
Wood Jr. is a correspondent on the Daily Show. His stand-up special Father Figure premiered on Comedy Central last month.
One time I opened for him [at Punch Line San Francisco]—this was shortly after he got back from South Africa, after he left Comedy Central—and he would play San Francisco a lot. And he would do super long sets. One night he did a set, a 4 hour and 59 minute set, that probably didn’t start until like 1 in the morning. When people left, the sun was rising.
In the middle of the set, he had to go to the bathroom, and I was in the back of the club because I’d opened. He had me come on stage while he went to the bathroom. The audience was paying attention to him the whole night, so when I went on stage, you could tell they sort of turned off for a second because they were exhausted—it was like 4 in the morning. Then when he got back on stage again they woke back up. Like a computer, they went to sleep for the two minutes I was on stage while he peed. Then when he came back on stage, they powered back up again.
It a pretty unique moment, but something I will always remember: The power of Chappelle to keep people’s attention for four hours in the middle of the night. That I don’t have.
I live in the Bay Area, so I’ve been seeing him since I moved out here in ’97. I remember seeing him at the Punch Line one night, way before Chappelle’s Show, when he went on stage in a Klan outfit. Later, we were all like, “Oh, that was the beginning of Clayton Bigsby.” I remember him being on stage at the Punch Line one night talking about, “I just filmed a movie that’s all about weed.” He was around here, not from the beginning, but from before he became a big star.
I think he was probably working on those [Chappelle’s Show] ideas before. It was a funny idea because he was on stage wearing a Klan outfit. The comics all knew it was him, but even if his audience didn’t, you could see he was black because of his hands and his arms.
Bell stars in CNN’s United Shades of America and hosts the podcast Denzel Washington Is The Greatest Actor Of All Time Period.
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.
Kweli was a featured artist in Dave Chappelle’s Block Party. He’s grown to become a known activist and has founded the record label Javotti Media in 2011.