It was a routine Wednesday at the Comedy Cellar in N.Y.C….until Dave Chappelle dropped in for a surprise set. The unicorn of comedy then proceeded to invite a few famous audience members onstage for what morphed into a kind of roast/toast/love-in/improv session—and an instant classic in the annals of funny. On the eve of Chappelle’s five-night run at Radio City this month—his biggest professional moment in more than a decade—we asked the guys who were there that night (including the unicorn himself) a simple question: How the hell did this happen?
Chris Rock: Dave is like Prince.
Marlon Wayans: Like Bigfoot. You know he exists, but he’s the hardest guy to lock down.
Rock: You never know when he’s going to show up. That night was a comedy booty call from Dave. [in Chappelle’s voice]”I’m in town, man! You should come on down!” Dave’s my favorite comedian. So…
Ahmir “Questlove” Thompson: I was on a date in Brooklyn, and I was trying not to look at my phone, but I heard a beep and saw the name Rock: “I’m down here at the Cellar. Chappelle’s going on in twenty minutes.” That was the fastest “Check, please!” I’ve ever said in my life.
Wayans: I was out with Bill [Bellamy] after a Knicks game and hit Kevin [Hart] up. He was in town to host SNL. He was like, “Yo, I’m at the Comedy Cellar. Chappelle and Rock are here.” I was like, “Word. Let’s go.”
Thompson: I lied to my date and said I’d been called into the studio. I can always blame it on D’Angelo, because he’s like the musical booty call. He’ll call and say, “Hey, what are you doing? I want to lay a track down. Come on over.” So once I call my date a car service, I get myself a cab. I tell my driver to “do 100! We’ve got fifteen minutes to get to the Comedy Cellar!” And I was not the only one pulling up to the curb and running inside like their life depended on it. The entire black comedy world was breaking their necks to get in. Inside, there’s a special table that only the comics sit at. It’s like the big-kids’ table. And the first thing I notice is it’s the black Last Supper. I grabbed the only seat left: There’s a piano onstage, and I took the bench.
Kevin Hart: Chris does his set, and when he comes off the stage, Dave comes in. So me and Chris went and sat in the back to watch.
Thompson: Chappelle gets up and riffs for forty-five minutes about—who’s the guy with the prosthetic legs? Oscar Pistorius? Dave was talking about how Pistorius would be the least vulnerable guy in prison, because all he has to do is scrape his legs on the steel bars every night. He started making this sharpening noise, and we were just done, all of us.
Hart: Me and Chris were joking about how Dave was just so much better than us—the thought process behind his jokes. How he makes it look effortless. We were all doing the same thing—running material we were working on. We were pretty much all in the gym—basketball players getting our jump shots. And Dave’s way of doing it was just levels above. He’s in a different realm. He’s out of this world, man. Ridiculous.
Bill Bellamy: Me and Marlon walk in, and Dave is onstage.
Wayans: He was talking about this crazy shit. He was balling out of control, like he wants to start doing weird shit, like showing up at places in helium balloons.
Bellamy: When Dave was 18 or so, I hosted a night at this club in East Orange, New Jersey—the Peppermint Lounge—where he used to perform. So I know if he sees me, he’s gonna go crazy. He sees me. He says, “People, this is unbelievable. I think I’m having a flashback.”
Thompson: Then, one by one, he just called them up, kind of like the Harlem Globetrotters’ Magic Circle.
Bellamy: Kevin Hart walks out. And here comes Chris Rock. People go goddamn crazy. Then Dave was like, “Who else is in here?” That was rich. So then me and Marlon come up. And we just start passing the microphone, telling stories about each other. It was a Black Pack moment.
Wayans: The stage is small as all hell. It’s like—put it this way, my house growing up in the projects probably was slightly bigger than that stage. Thank God there wasn’t ten of us on it.
Hart: We started telling about some of the first things that we did with one another, the first times that we met. We were segueing between each other. Someone’s talking about Bill’s Peppermint Lounge and how people used to go over there and bomb.
Bellamy: It was organic. I knew it was magical, based on the reactions of the people at the Cellar. They were like, “Oh, my God!” I told a story about one time, Dave was standing outside my club looking lost, just a little skinny kid from D.C., not famous yet. And he needed a ride home. And I gave him a ride back to New York. I had this real fly car at the time, a brand-new Acura, and he was like, “Man, when I get rich, I’ve got to get me one of these.”
Thompson: Chris was very quiet—just wisely playing the back. He played it real cool, and then when he had a moment, he said what he had to say, and it was hilarious.
Rock: I’m a hanger backer, anyway, in life. I’m the oldest of seven. So I’m used to letting my younger brothers do whatever they’re gonna do. I was literally just enjoying the moment. You know, we’re not musicians. We’re not in a band. Comedians, if you get good, you’re always out there by yourself. Stand-ups are boxers. They generate the most excitement of anyone in sports, and they have the saddest endings. People wonder why guys get really famous and stop doing stand-up. It’s fucking lonely. The times that you’re onstage with somebody of your level of success are very rare. The other thing is we’re all grown-ups. If this had happened twenty years earlier, there might have been a fight onstage. But now everybody’s been married. Everybody has kids. Divorces. We’re all very secure in who we are. That was an essential element. The evening would not have happened without that.
Hart: It was a highlight of my life. It was Dave’s thing. I’m telling you. We were up there watching Dave. Being fans. Fans of Chappelle.
Rock: Dave’s got the best quote about comedy I’ve ever heard. He says, “Comedy is a language I speak well.” That’s what it feels like with him. It doesn’t feel like an act. It feels like a guy speaking his first language. He’s so natural with it. He takes his time. He’s got a lot of Bill Cosby in him. We hear cursing and sex and we think Richard Pryor. But to me, Dave’s closer to Cosby than anybody. He has the balls to take his time and set something up.
Hart: That crowd got something money can’t buy. They got authenticity.
Rock: Yeah, it was kind of a lovefest. Though I’m not a sentimental guy. Anytime it gets too sappy, somebody’s got to say some funny shit.
Bellamy: I remember Chris saying Marlon fucked one of his ex-girlfriends.
Wayans: Dave says something about my mama’s vagina, about her having ten kids. I said, “Don’t make me call all the Negroes that came up out that vagina. You don’t want to get the Wayans beat-down.” He goes, “Oh, please don’t call them niggas.” Then Kev told this story about how he spilled liquor on Beyoncé once, and all of us was like, “Time out, Negro. Your stories are starting to include people that normal people don’t hang out with.” That’s when you know you’re making too much money.
Bellamy: Chris said something to Kevin that congratulated him on his success—but it was like, “You may be hot right now, but Dave Chappelle is hot forever.”
Rock: You’re not going to sit there and let other people be funnier than you. I mean, I like Kevin, but come on. I’m not conceding. Please. Kevin starred in Soul Plane. So, you tell him that you love him, but you got to remind him of Soul Plane.
Wayans: Everybody on that stage was different. Dave is the kind of guy that takes years to make a painting and then goes, “Nah, I don’t want to sell it. I’ll put it in this gallery for a little bit of time, but I’m not going to sell it.” Chris is the kind of guy who will draw something, erase it, draw it again, erase it, draw it again a different way, erase it, draw it in color, erase it, fill it out, erase it. You know, Chris is an artist like that. Like a mad scientist putting down comedic formulas. And Kev—Kev is one of those guys that makes a painting and says, “This is the greatest painting ever.” And you go, “Wow, that is a great-ass painting!” And you had no idea he had the time to even draw it. Bill has been doing it so long that he’s just a master of ceremony. He always puts out something that you go, “Man, that’s some good art right there.” You know, “How come this didn’t sell for $100 million?” You know? And Bill, not only are his paintings good, but, you know, he has a good canvas. You know, he’s a good-looking dude. It’s hard for people to root for the fine nigga, but Bill, you know, Bill has been doing this for twenty years, and consistently. Me? I’m just learning how to paint.
Bellamy: This was a moment when we wasn’t working, we wasn’t in the hustle and bustle. We were just in the club where it all started for everybody, and we could say how much we love and appreciate each other’s talent. It wasn’t a roast. It was a tribute.
Wayans: It could have been thirty minutes. It could have been an hour. I’m not sure, because time was going by so fast because we was all laughing so much. And Quest is just up there like hitting the piano sometimes when some jokes are out of bounds.
Thompson: It was about being a witness to a great moment. I gave up a great date with a hot girl. I threw it away just to rush to this club to watch history.
Rock: And it’ll never happen again. There’s no Coachella of comedy where we all get together, you know? There was definitely an afterglow. I remember coming back to the club a few nights later and thinking I was gonna go on, but—eh. Everything felt like a letdown after that for a minute. Like: I don’t feel like getting on a lonely stage right now.
Dave Chappelle: I had no idea all those guys were going to be there. You know, comedy is surprisingly competitive. It’s like being in the Karate Kidtournament every night. I’ve known these guys for years and have always respected their talent, but on that night I got to experience it up close. That’s why it was special. But it made me laugh that Ahmir told his date he needed to go to the studio. Why didn’t he just bring her to the show?
This is an extended version of the story.