How Dave Chappelle Pulls Everything Off

Welcome to Mass Chappelle. It’s a celebration (bitches) of the two new Dave Chappelle standup comedy specials that Netlix will release on Tuesday. We’ll be giving you interviews, insights and examinations of one the funniest people living today.

Corey Smyth is Dave Chappelle’s business partner and helps him pull off some of his most ambitious ideas. Smyth manages Vince Staples and has worked with artists including Chad Hugo of the Neptunes, De La Soul and Black Star. Smyth has helped pull of projects including setting up Chappelle’s 10 days of comedy sets and concerts at New York’s Radio City Music Hall in 2014, booking the musical guests for Chappelle’s Show and putting together a free mini-fest in Brooklyn in 2004, which was filmed for the Michel Gondry-directed documentary Dave Chappelle’s Block Party.

Here Smyth tells us about how he and Chappelle make it all happen.

After Chappelle returned to doing standup, had he done any big shows in New York before the 10-day run at Radio City Music Hall?


We had done the Gramercy [Theatre] and some other things, but Radio City at that point was a bigger idea, it was a bigger undertaking. He had an idea to do something that I don’t think anyone else had done at that point at Radio City. We had done a show at Radio City a long time ago, though. It was right when the Apple Store, the 59th Street one, had opened. The day that store opened we went and got laptops.

In this much bigger undertaking, how far in advance did you guys have it planned out?


I would just say a few months. We were going to do a combination of music and comedy shows. Things went on sale, the comedy shows went on sale first and then, afterwards, we were going to strategically leak the music shows after the comedy shows had sold out.

We had Nas, Erykah Badu, the Roots, Janelle Monae. We had Premier and Busta do a medley, and then we had Mos [Def] do a medley because Mos was coming back to the States at that point. Then Kanye came and did a surprise set.

Also, we had rehearsals because we had the orchestra. We had a 60-piece orchestra. We had to get sheet music in place. There was a lot going on.

Was it always the intention to do 10 shows or did it build as the demand became so obvious?


No, the idea was to do 10. We didn’t go into it letting the world know we’d do 10 shows and 60,000 tickets—but it worked out.

What was the reasoning for choosing Radio City Music Hall as the venue?


I think you can answer that one yourself. It’s Radio City Music Hall. Where else in New York would stand out on that level?

I guess Carnegie Hall.


Yeah, Carnegie Hall could, but it’s not the same. No disrespect, but it’s not the same.

[Radio City is] a cornerstone of New York. If you’re painting a picture of New York City and it doesn’t have Radio City in it… It’s one of our monuments: the Statue of Liberty, Empire State Building, Radio City, Central Park, it used to be the Twin Towers, now it’s the Freedom Tower.

Watching Chappelle’s career it feels like these very big things come together very quickly, or just all of a sudden this big thing is happening. Is that the reality?


It’s a combination of both. Sometimes there are things that come together in a timeframe that most artists and talent don’t have the luxury of pulling together the way he does. Sometimes there are things that have been thought out and worked on for a longer period of time, but when we pull the trigger, we pull the trigger. A lot of these things are ideas for a long time, it’s just when Dave says, “Go.” The thing about it is, when Dave says, “Go,” you’ve got to be ready to go.

You mainly work with musicians, so how did you start working with Chappelle?


Dave and I became fast friends in 1999, I think it was at a De La and Talib Kweli show at Kenyon College, Ohio. It took on a business relationship around when he decided he was going to do Chappelle’s Show, right around the pitching stage of the show when he and Neal [Brennan] were starting to write the show. He came to me and asked if I would…I feel like it was an ask, but it was also like, “This is what we’re doing. We’re about to do a show and we want you to do all the music for the show.”

I came on board and booked all the music and came up with the artists and put together concepts for their performances and went out and got a group of our friends to appear on the show. It wasn’t an easy undertaking in the beginning. It was a lot more difficult than people would think to get people to show up for the show.

Mos, being who he was and my friend at the time and Dave’s friend at the time, was on our pilot episode. There weren’t that many people that I could get at that moment.

When did it make that turn where artists were saying, “Oh, we’ll definitely do this”?


Towards the second part of season two, going into season three, the phone was just ringing.

[The TV audience] was really white male college heavy in the beginning. Then by the time season two hit, it just became a cultural thing. It was everywhere.

Were you surprised when Common decided to take his live performance of “The Food” from ‘Chappelle’s Show’ and swap it onto the album ‘Be’?


I wasn’t surprised. When we did “The Food” that day we had them set up in a different location and Kanye was just like, “Nah, we shouldn’t be performing back here.” I think we had them in a lounge. He was like, “Yo, we should do it in the kitchen.” It’s TV, it’s not like we had that big of a production, but we still had to shift the whole production from where we were to the kitchen, and it was dope.

The whole pitch of the show [to musicians] was, “Here’s an opportunity to do songs that you normally wouldn’t do. They’re not your singles, per se. Let’s create a video for them, almost.” We had De La perform on the tour bus, Kweli at the bottom of the Brooklyn Bridge, Mos Def in the SUV with Dave—which obviously was like the start of “Carpool Karaoke.”

These were things that we were just doing because there was an opportunity that we wanted to afford artists so it wouldn’t be stagnant, so it felt like they could be as creative as they wanted to be and we would support that as well.

Where did the idea for Block Party come from?


A film called Wattstax. Dave just saw it and was like, “I want to do something like that.”

Dave knows a lot of music, knows a lot of comedy. Dave watches a lot of things. I had never seen it and he told me to go find a copy of it. The only copy I could it find at that time was at a place called Kim’s. It was a video store in the Village on 8th Street. [Wattstax] was on two VHS tapes and I watched it and called him back and was like, “Okay, I get it, let’s go.”

Everyone showed up, but logistically it was a difficult thing to do. There were a lot of naysayers going into that one because we only had one day. We had a budget to shoot one day, we had no money for an alternate rain date or any of those things. As it would be, it rained crazily overnight and that morning, so we had to get the streets pumped out by the fire department. There was so much going on with that one, but that was my first film. For it to be my first film, it was a huge success.

That was one where I feel that you get to the point where you’ve done it and you know what it’s supposed to be, and now you’re managing the situation and the expectations of the people around you to make sure everyone’s delivering for Dave. That’s really what it is.

What’s exciting about him is that you don’t really know what you’re going to get. Each experience is different with him.


You know what you’re going to get, though. You’re going to get something great, he’s not going to give you anything mediocre, ever.

Right, but some audience members are like, “Well, my friend went to the show and he said Chappelle talked about this, and that sounds great, so I want to see it.” But you might not get that.


Yeah, you’re not going to get that same thing. That’s intentional. How much fun would it be for him to do that over and over again?

That’s why bands break up, right?


Yeah, so it’s getting the audience to understand or change their expectations of what’s going to happen and think about what the performer’s doing, that it is a two-way street. It’s not just them performing for you, the performer has to be into what they’re doing as well.

I think [Chappelle has] developed and trained an audience in a very unique way that most comedians wish they could, because his core fanbase knows you sit and you wait, because he’s going to give you something. You’ve just got to wait. He’s not sitting here with punchlines, that’s not what he does, that’s not his style.

He has a pattern and a pacing that I would challenge anyone to say that they’ve seen on that level. Dave introduced me to comedy, but throughout that process, I think Dave’s the best I’ve ever seen in my life and I’ve been around the rooms enough now to say that.


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