David: Hello there. Welcome to another edition of Lexicon Late Night, as always here with my co-host Justin. Today we’re going to talk about Dave Chappelle. As always in these episodes, we talk about the greatest storytellers of all time, and Chappelle has an argument to be part of that conversation. He’s been at the top of his game for three decades.

Justin: I’ve been a fan of this man for 26 years.

David: Yeah. So Dave Chappelle, another one of the comedians on the Greatest of All Time list. This is our fourth or fifth, I think at this point. 

Justin: Yeah, yeah. More comedians than any other kinds of storytellers.

David: I think we’ll get into why that is today. Like, comedians are the ones who can speak the truth.

Justin: Yeah, yeah. The voice of reason. The conscience of the nation. Chappelle, definitely argument that he’s the greatest comedian of all time. Definitely my favorite comedian of all time. Or at least top three, for sure.

David: Louis, probably?

Justin: Yeah, Louis. Yeah. Norm MacDonald, of course. Yeah, he’s in the top. He’s up there. He’s on Mount Rushmore, for sure. 

David: For sure. 

Justin: He was actually, we haven’t even jumped in yet, and I’m already going off on a tangent. But he’s the reason that I learned that stand up comedy was a genuine art form from discovering his comedy. Because in Canada, on the Comedy Network TV station, there’s always the Just for Laughs comedy festival, and it’s just guys doing five minute sets, and the vast majority of them are just hacks. So some of them would be funny. You catch a little five minute clip, but mainly I’m going like, oh, I’m, you know, 12 years old going like, okay, kind of funny, I guess. These guys are just like clowns. But then I went over to a buddy’s place and he had HBO and Dave Chappelle’s first big special, Killin’ Them Softly, was playing. So hour-long special, and it blew my mind. I had no idea that comedy could be like this, that in-depth, that much social commentary, that much storytelling, really.

David: Explain to the folks at home what a hack is.

Justin: A hack coming from the term ‘hackneyed’ is a comedian who just makes very obvious, played-out, common jokes. We’re here in Bangkok. Anyone who makes a joke of, well, you came here to Bang Cock, didn’t you? There. That’s a hack joke.

David: Yes. And Chappelle was here in Bangkok. He did not make that joke.

Justin: No, he did not. He had other jokes on the same subject matter which actually surprised you. So basically, a hack is someone who’s doing a joke that’s just obvious and doesn’t have any kind of twist or surprise or any kind of deeper meaning to it. It’s just obvious. 

David: Yeah, it’s obviously a comedy term, but it really can apply to anything. Like Disney these days is a hack. Disney just puts out crap.

Justin: Yeah, yeah. Any live-action remake of a Disney movie is very, very hack material.

Justin: Indeed. All right. So lessons that business leaders can learn from the greatest comedian of all time, arguably, Dave Chappelle.

David: Arguably, definitely.

Justin: Number one. One that we always talk about when we talk about comedians is persona. 

David: And there’s a reason for it. It’s the reason that these people resonate through time. Like one of our recent episodes, we’ve got Mark Twain, again, a very distinct persona through time. 

Justin: And of course, Dave Chappelle recently, a couple of years ago, won the Mark Twain Prize. There we go. There we go. 

David: So, yeah, persona matters a lot because especially in this age of constant information, what resonates is people who seem authentic and authentic on TikTok and Instagram with the filters and stuff. Not that kind of authenticity, but someone who speaks with a consistent voice that’s true. And I think no one, even no comedian, has a stronger persona than Chappelle. That voice. 

Justin: And even just tone of voice.

David: Yeah, literally.

Justin: In the early days, he’s got that kind of. How old is 15, really? What you doing here, baby?

Justin: Yeah. Hey, baby.

Justin: So like literal actual tone of his voice, but also just kind of the persona and what he’s saying. And it’s evolved brilliantly over time. When he started out, it was kind of brash, kind of in-your-face. And now with age and many, many cigarettes, it’s kind of mellowed and matured a little bit.

David: How does it sound, though?

Justin: I’m no. I’m no Dan Soder, but. Forty years.

David: That’s pretty good, yeah. Because we talk about tone of voice all the time in these things, but we’ve never actually had an example of like, such a literal tone. That’s changed, yeah. And obviously, as a comedian, you need a strong tone of voice. As a business person, you do too. And, yeah. His tone of voice literally, but also in thematically. 

Justin: Yeah. Yeah, for sure. And that actually. Point one and point two are kind of combined or complementary to each other. It’s the themes that he tackles. They’re not hack. They’re not obvious subjects to tackle and confront. And so, I mean, we were talking about what to really discuss here on the show now. And it’s kind of like he’s almost like a healing figure for society because he attacks these controversial topics like really head on. And you said it’s like lancing the boil.

David: Yeah, totally. That’s something that he almost alone has. Like when there’s an election, SNL invites him to be the host afterwards to, like, calm the nation down or encourage the nation. Yeah. That’s mainstream TV. That’s like prime time.

Justin: : Right. And it’s like, okay, call in current day Mark Twain and get everyone to chill out a little bit. 

David: Exactly. Despite the fact that constantly for 20 years plus someone’s attacking him all the time for something that he said. It’s a different group every five years, but someone’s always attacking him because he isn’t afraid to just say what he thinks, and he couches it in comedy, obviously he makes things accessible, but that’s the lancing the boil aspect. He takes you into these uncomfortable areas that maybe you don’t want to go to. Takes you there, makes you laugh, and then you accept it.

David: Yeah, yeah.

Justin: And this is pure comedy: building tension, taking people, like, right to the edge of their comfort zone, maybe a little bit over it and then resolving it. It’s therapeutic in a sense. 

David:  Yeah. And that’s a good kind of like, almost like Messiah-type character. But like, obviously America has a lot of issues and always does. And a lot of them are racial. And Chappelle is someone that I think everyone has respect for as a result of his consistent authenticity. He’s never sold out, literally refused to sell out.

Justin: Yeah.

David: Do you think we’ll get to later? 

Justin: Yes. Yeah. 

David: And yeah, racial tension in America is always high. And in the Chappelle Show especially, he was always like taking into those. The first ever episode. The first scene of the first episode is the black KKK guy.

Justin: Yeah, sure. And we’ll actually we’ll probably tee up a clip right here. 

David: All right. Divorced his wife. Didn’t see that coming. 

Justin: Yeah. It’s such a brilliant way to obviously tackle an extremely difficult, fraught subject matter. Yeah, but it’s genius, right? 

David: Because it’s like it doesn’t matter at all. Like, none of this matters. It’s ridiculous. And by framing it in that manner, the absurdity of it becomes ever more apparent. Like, yeah, we’re not as humans as where we need to be evolutionarily intelligence wise. But those kind of things, I think, help us to see our hypocrisies. And that’s why he’s brilliant. That’s not a funny, the clip is funny, but the idea behind it is a genuinely meaningful societal, noble thing.

Justin: Yeah. Yeah. Absolutely. And like, these are challenging topics, you know. Like, you think of, like one of my favorite bits of his is how old is 15 really. Which we’re not we’re not going to play the clip. That’s tough. And he’s attacking it head on. But then, it’s almost the same thing we were doing in the Patrice episode. We mentioned that he’ll purposely say something so outrageous that kind of divides the room and shocks the room, and then he’s skillful enough to kind of dig his way out of the hole and then provide that resolution where everyone now, okay, now we’re all back. 

David: Well, that’s a great comedian, but it’s also a great storyteller. Like any good storyteller, I kind of want to go to an uncomfortable place like Stanley Kubrick is the master of this. Like A Clockwork Orange is a horrible movie, but you leave it kind of, it changes you. It changes your perspective on things. That’s what good art does. And he does that too. And obviously he does it in a funny way, like the racial draft in Chappelle’s Show.

Justin: Sure, yeah.

David: Kind of leans into these like those tensions between all races. Yeah. And there doesn’t need to be. And we’ve got loads in common, and that’s a fun way to do it. Like the Chinese drafting the Wu-Tang clan.

David: Yeah, yeah, the whites took Tiger Woods.

Justin: Who got Tiger Woods? The whites?

David: Oh, really? Sure. I think we gave them Condoleezza Rice and Colin Powell, they threw him in.

Justin: Oh, okay. Threw them in a deal. All right. We came out okay. Yeah. Who got Eminem, I think blacks got Eminem, no? Okay. We’ll have to go back and look at the clip.

David: So yeah, like his show was probably the peak of this. Yeah. But since then like he went away for a while he came back. And since he came back with his standup he’s caused a lot of controversy with a lot of his statements. Honestly, not been as funny as in his earlier years, but it’s a different kind of, as you said, he’s a statesman, like.

Justin: Yeah, yeah. He’s being Mark Twain.

David: Yeah.

Justin: Or George Carlin almost. And there’s a consistent kind of moral clarity. Whether you disagree with him or agree with him. He is taking a stance, and he’s being consistent to how he sees the world and kind of like an equal opportunity offender. The same thing we were talking about is why South Park has been so successful. For so long is that they don’t left, right, whatever issue they take their stance and they don’t really care who they offend because they’ve got something to say. And then that authenticity really carries them. 

David: Yeah, it really is a tricky one though, because like, you lose corporate America when you do that, you lose endorsements, you lose adverts, you lose Hollywood movies. But onto the next point.

Justin: Yeah. Well, as you’re saying, like obviously Chappelle’s Show extremely successful. And then he was offered $50 million to continue and turned it down and walked away entirely and even quit standup for a while because we don’t need to get super into the details and theories as to why he did this, but really, he just didn’t like what his prospects looked like. I have to do this for the next couple of years. I’m not going to do that. Take a stand. And just when you don’t like doing something and you don’t think it’s going to be valuable to you or to your audience, take a step back. And then he did that and came back. And for a while he was kind of in no man’s land. Nobody knew what was going to happen to him. And then came back with this big Netflix series of specials where he’s got way more money now than he would have doing the sketch show, doing Chappelle’s Show again. Okay, so so before we get into that, what’s the lesson for business leaders. 

David: So yeah, Chappelle’s resonance through time, it shows that the winds are going to blow against you often. You don’t need to let them knock you over. Obviously, if you’re like a pop star, if you’re Katy Perry or whatever, then you need to kind of go with the trends. But for Chappelle, he went with his own direction. For companies, there is a lot of pressure always to be chasing trends.

Justin: Sure. Yeah. I mean ESG, DEI, sustainability. Or even in our clients, B2B companies that want to be on TikTok, right? It’s not really.

Justin: Oh, sure, yeah.

David: It doesn’t really makes sense. But for the stuff you mentioned too, like it’s there’s every single day of the year there is an issue. 

Justin: There’s always a month.

David: Yeah. Day or a month or a week or whatever.

Justin: Yeah.

David: And there’s no problem with associating yourself with any of those things, celebrating them. But your whole marketing output can’t be every single day of the year, International Toast Day or whatever.

Justin: Sure, sure. And we actually kind of advise our clients against this because, I mean, as you said, every day is some kind of day, every month is some kind of month. Yeah. So if you’re going to paint yourself into a corner where you have to address every single one of these holidays, and if you’re in like a multi ethnic, multi-religious society, then there’s all three religions and whatever. Like if you’re in Singapore, for example. Um, so. 

David: But if you’re a company, you should have a business strategy, right? What are your core values? What do you what you actually stand for? And then when it comes to marketing, you have your content pillars, right?

Justin: Sure. 

David: So if there’s natural fit into any of those things with any issue, fantastic. If you’re a company that’s focusing on women’s rights, then, you should definitely be celebrating International Women’s Day. Or if you’re a company that’s focusing on sustainable energy, then of course, sustainability. But these things can come across as really inauthentic.

Justin: Yeah. I mean, that’s exactly what I was going to say. You took the words right out of my mouth there. Only do it if it’s authentic. If you’re genuinely leading in sustainability, then make, as you said, sustainability a content pillar. And then on Earth Day, by all means do some kind of Earth Day content thing. But if you’re just doing it as a box ticking. Hey, look at me. It’s just it’s going to come across as inauthentic. It’s same with DEI and same with ESG and anything else. 

David: It’s always been true with Pride Month. It’s always been like these massive MNCs pushing pride in America, but in the Middle East because they’re not.

David: Yeah, sure.

Justin: They’ll put the rainbow on their flag in Canada or the UK or even here in Thailand now. So props to Thailand. But they’re not going to do it. 

David:  Exactly. Now Trump’s won the election. People are less focused on Pride Month. If it ever mattered to you, it should always matter to you.

Justin: Right.

David: But if you’re just chasing a trend, it’s disgusting. Like, no one should be supporting businesses that are inauthentic like that. Stand for something I believe in, something that’s amazing. But if you stand for everything, you stand for nothing.

Justin: Yeah.

Justin: Yeah. If you stand for nothing, you fall for everything. Public Enemy.

David: Yes.

Justin: Right.

David: That was a good lesson.

Justin: No, no, absolutely. It’s just I’m now looking at how to bring this back to Dave Chappelle. 

David: So Chappelle walked away from the Chappelle Show.

Justin: Yes. Walked away from the Chappelle’s Show. Obviously, massive financial.

David: Yeah. It was probably the most popular show in the world, probably. 

Justin: Yeah, yeah. And he was offered $50 million for.

David: Yeah, I’m not sure, but definitely to continue it for more seasons. And it’s $50 million in 2002.

Justin: Yeah, yeah.

David: So adjusted for inflation. $10 billion dollars.

David: Yeah.

Justin: And at the time, he kind of disappeared for a while. He didn’t have any more stand up comedy specials. He certainly wasn’t doing Chappelle’s Show, wasn’t doing all the late night talk shows and all this stuff. At least 10 years, right?

David: So we didn’t.

Justin: Yeah, for a while. And we really didn’t know what he did. Like Inside the Actor’s Studio.

David: Yes.

Justin: Which a great episode. And we’ll actually throw up a little. Oh, and Oprah too. Um, and so setting aside all the reasons for that, he came back focusing on what made him great in the first place, which is standup comedy and then achieved financially, but also culturally, way more success than he probably could have achieved doing something that he felt wasn’t him anymore.

David: Yeah. And I think the lesson is focusing on the core because

Justin: Outsource the rest.

David: Exactly. I think he, I don’t want to get into all the Chappelle’s Show reasons, but part of it was that every time we did stand up, it would be like, ‘I’m rich beep. Yeah. Right. 

Justin: And he’s like, well, he has one of the bits in For What It’s Worth, his special. He’s at Disney World with his kids, and Mickey Mouse is saying, Rick James, would you not call me a _____ in front of my kids?

David: Exactly. Yeah. Yeah. So, like, for him, his passion is stand up. Everything else is a way to make money. So, like, he was crushing Chappelle’s Show, but his standup was being destroyed, and that’s where the ideas come from. 

Justin: Yeah. And he also in the Oprah interview and Inside the Actor’s Studio not to get super into the details of this, but just said I felt like people weren’t getting the original point of what it was for and that I was just doing something. So now I’m just kind of I’m an entertainer where I’m not being. And our second point was authenticity, and that’s what it’s all about. So his return to just standup after taking a pretty lengthy hiatus, super successful and some of the best work he’s done. I mean, you said maybe not as hilarious as his earlier work, but it’s profound, deep Mark Twain-style work now. 

David: And it was a risk, you know, just, you do stand up, right?

Justin: Yeah.

David: 50 million. Probably more than you would make in the whole weekend. 

Justin: Won’t see me on this show, actually. 

David: But, for any stand up, $50 million is probably not what you’d ever make in your career. So to give up that and come back to what his core was, that’s a really, really hard thing to do. But he makes more money now because he was true to himself. 

Justin: So, it’s a risk to not take that money for sure. But what people might not be seeing is it’s a massive risk to actually take that money.

David: Yeah.

Justin: And then you’re painted into that corner and you’re locked into a long-term contract doing something you don’t want to be doing.

David: Yeah. And your brand is that now.

Justin: And you’re stretching yourself too thin and it’s going to harm your reputation. And, you know, we’re gonna tie this to our own experience as a company, extending too many service lines that are not core. 

David: That’s what we do. That’s what we do at Lexicon Late Night. So yeah, absolutely. Like us we were very fortunate that we came up strong. So we had loads of opportunities. So we started to do a lot of different things. We grew the business really quickly. But the core of the business is storytelling for companies. We help them tell a story through social media, LinkedIn, personal branding, video production. You can be tempted to chase the easy bucks, but you lose a lot from that. Like you gain in the short term. But you’re losing the long term because you dilute your brand by not offering the best possible product, but you also lose the core of the business, you lose the core of who you are. You sell your soul, basically.

Justin: Yeah, yeah. For a quick buck.

David: Yeah. So there’s always going to be a trend. Try not to chase trends. I guess it’s the lesson. Like, don’t be on TikTok if you think.

Justin: There you go.

David: If you’re selling professional services or recruitment services or accounting. Or you can just waste a lot of money and get nowhere because that’s not where your audience is.

David: Yeah.

Justin: Yeah, absolutely. So to recap here, business lessons from Dave Chappelle. Tone of voice persona, develop that, perfect that, but evolve it over time. Second lesson: Don’t do it unless it means something. Be authentic. And third lesson: Know what your core is. Stay true to your core.

David: Yeah, absolutely. And in all of these great storytellers that we focus on, these lessons, they’re almost universal lessons. They stand the test of time, because they actually, they’re what matters. You know, the wind blows in many directions. Trends come and go. But authenticity, realness stands the test of time.

Justin: Chappelle’s Show.