Club Shay Shay - Donnell Rawlings Part 1

Summary

Club Shay Shay: Donnell Rawlings Part 1 – Detailed Summary

Episode Overview In this engaging episode of Club Shay Shay, NFL legend Shannon Sharpe hosts Donnell Rawlings alongside comedian Dave Chappelle. The conversation delves deep into their respective careers, the evolution of stand-up comedy, acting experiences, and personal insights into the entertainment industry. The setting is the exclusive Villa 66 at Resorts World in Las Vegas, providing a vibrant backdrop for the candid discussions.

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1. Introduction and Setting

Shannon Sharpe introduces the venue—a luxurious two-bedroom entertainment villa located on the 66th floor of Resorts World, offering panoramic views of the Las Vegas Strip. He highlights the exclusivity of the event, reserved for invited guests, setting the stage for an intimate and insightful conversation.

Quote:

• Shannon Sharpe [05:00]: "Today we're at the brand new Villa 66 at Resorts World in Las Vegas. This is a spectacular two-bedroom entertainment villa on the 66th floor with a stunning view of the strip."

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2. Guest Profiles

Shannon provides a comprehensive introduction of Donnell Rawlings, emphasizing his significant impact on the entertainment industry through roles in acclaimed television shows like The Wire and Chappelle's Show. Dave Chappelle adds his personal admiration for Donnell, noting their shared experiences and mutual respect.

Quotes:

• Shannon Sharpe [02:50]: "The guy that's stopping by for conversation on the drink today is one of the most beloved comedians in the industry... a versatile performer, seasoned standup comedian, host, a writer for over 30 years."
• Dave Chappelle [03:58]: "It's ironic that he's one of my favorite artists right now. And I love Teddy's drinks."

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3. Evolution of Stand-Up Comedy

The discussion shifts to the transformation of stand-up comedy over the years. Dave Chappelle critiques the current trend of skit-driven comedy, contrasting it with the traditional stand-up style he and Donnell embodied. They express a desire for younger comedians to respect the craft and strive for excellence beyond viral skits.

Quotes:

• Dave Chappelle [10:28]: "The reason why it was like that, we didn't have access to what the kids have today to blow up... I just wish that some of them just would respect the art enough to take it a little bit more serious."
• Shannon Sharpe [09:12]: "I noticed a difference, but I will say it's evolved."

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4. Acting in Acclaimed Series: The Wire

Donnell Rawlings shares his journey into acting, particularly his role in The Wire. He recounts how he was initially cast without formal acting training and how his authentic portrayal led to expanded roles in subsequent seasons. The conversation highlights the loyalty of creator David Simon towards his ensemble cast.

Quotes:

• Donnell Rawlings [20:10]: "When I came on set, he said, you know, we had you heavily favored to play the role of Omar... we wouldn't have had the platform for people to see what to do."
• Dave Chappelle [22:21]: "No role is easy for me to play because I'm more connected to stand up than acting... I booked the role."

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5. Partnership and Dynamics on Chappelle's Show

Shannon and Dave delve into the dynamics of working on Chappelle's Show. Dave discusses his role as the warm-up comedian and his creative contributions, including improvised characters like Ashley Larry. He emphasizes the importance of chemistry and improvisation in sketch comedy.

Quotes:

• Dave Chappelle [74:10]: "I didn't. Well, the character on paper, he was just a guy that had boxers on and dress shoes and stole his girl's money... I went to Danielle, I told him, 'Give me some baby powder...'"

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6. Navigating Success and Relationships in Entertainment

The conversation addresses the challenges of achieving and maintaining success in the entertainment industry. Donnell emphasizes the importance of relationships and work ethics, while Dave reflects on his own experiences with financial struggles despite being part of successful shows.

Quotes:

• Donnell Rawlings [67:25]: "The one thing that I know about in this business now, the entertainment side of it, and when you have advertising and sponsors, it's all about relationships."
• Dave Chappelle [34:32]: "I wasn't successful then. I was working. I was successful. That's the illusion people have about TV."

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7. The Impact of Chappelle's Show and Legacy

Dave Chappelle discusses the unforeseen success of Chappelle's Show and its lasting impact on pop culture. He shares anecdotes about the show's influence, his role in its creation, and the relationships formed during its production. The narrative touches upon Chappelle's decision to step away from the show and its implications.

Quotes:

• Dave Chappelle [27:15]: "Two of the Days had 100 best shows in the history of TV... They are going to be talking about their shows until the end of time."
• Dave Chappelle [82:32]: "That would be a tough one. That would be tough."

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8. Reflections on Contemporary Comedy and Cultural Shifts

The duo reflects on the current state of comedy, societal changes, and the concept of cancel culture. Dave expresses optimism about the future of comedy, believing that audiences are moving away from restrictive norms. They discuss the potential for new platforms and formats in comedy.

Quotes:

• Dave Chappelle [85:56]: "I think control is what it is... Hollywood is up, okay?"
• Dave Chappelle [72:05]: "If you wanted to be respected in this business or if you want to be one of the best to do it, then I want my name to be on the same line out as the best to do it."

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9. Personal Anecdotes and Storytelling

Throughout the episode, Donnell and Dave share personal stories, providing listeners with a glimpse into their lives beyond the public eye. These anecdotes range from audition experiences to interactions with other industry professionals, showcasing their authenticity and camaraderie.

Quotes:

• Dave Chappelle [04:50]: "They don't talk a lot. Oh, man."
• Dave Chappelle [57:19]: "I told my agents, yo, let's go for these 33-year-old executives."

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10. Closing Remarks and Teasers for Part 2

As the conversation winds down, Shannon Sharpe informs listeners about the continuation of the discussion in Part 2, available on their preferred podcast platforms. The episode concludes with a light-hearted exchange, reinforcing the friendly rapport among the hosts and guests.

Quote:

• Donnell Rawlings [97:51]: "This concludes the first half of my conversation. Part two is also posted and you can access it on whichever podcast platform you just listened to part one on. Just simply go back to Club Shay Shay profile and I'll see you there."

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Notable Quotes with Timestamps

• Dave Chappelle [05:00]: "You can have a little bit of talent, but if you got the right work ethics, you can make it happen for yourself."

• Donnell Rawlings [20:10]: "If you really follow Wire, you notice a lot of people say first season was all about the towers... And that was because the Baltimore tourism board was complaining..."

• Dave Chappelle [34:32]: "When I was doing Chappelle's show, and the thing about it was, you heard me say I'm rich, bitch, at the end of her show, right?"

• Dave Chappelle [11:19]: "When you gotta figure out how to maneuver yourself through this business."

• Dave Chappelle [15:35]: "Their bosses, everybody got these people..."

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Conclusion This episode of Club Shay Shay offers a profound exploration of the entertainment industry's intricacies through the lenses of Donnell Rawlings and Dave Chappelle. From their humble beginnings to their ascent in comedy and acting, the conversation underscores the significance of hard work, authentic relationships, and staying true to one's craft. Listeners are left with valuable insights into navigating success, the evolution of stand-up comedy, and the enduring legacy of influential television shows.

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Note: This summary omits advertisement segments, introductions, and outros to focus solely on the substantive content of the conversation between Shannon Sharpe, Donnell Rawlings, and Dave Chappelle.

Transcript

[Shannon Sharpe]

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[Donnell Rawlings]

Off time at my house, there are a few things that are must haves on my checklist. My fellow friends and fans. Check my favorite jersey. It is good luck. Check an iconic drink that's a fan favorite.

[Dave Chappelle]

Check.

[Donnell Rawlings]

Hypnotic can turn any cocktail into an iconic creation. With its game changing color and tropical flavor, Hypnotic should be in everyone's starting five. I consider Hypnotic the point guard on my game day roster because not only is it versatile, like having it on the rocks or as a base for cocktails, it also finishes smooth. So grab a bottle of Hypnotic and make your next basketball watch party iconic. Enjoy the vibrant taste with friends and turn every game into a memorable celebration. Hypnotic where every sip is a slam dunk. Hypnotic Liqueur Bardstown, Kentucky 17% alcohol by volume Hypnotic reminds you to think wisely. Drink wisely.

[Shannon Sharpe]

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[Dave Chappelle]

I don't know nothing about the free parties, but I do know right now because you about to get crazy. Go ahead and say it. That's how diddy parties start, right? No, I'm just saying. Let me put my towel back on. I know you about to say some slick shit. I know. Yeah, that's how he gets you. Take the towel, start throwing your shit around. All my life. Been grinding. All my life.

[Teddy D]

Sacrifice hustle paid the price, want a slice, got to roll a dice that's.

[Dave Chappelle]

Why all my life I been grinding all my life all my life Been grinding all my life Sacrifice, hustle, paid.

[Teddy D]

The price, want a slice, got to roll a dice that's why all my.

[Dave Chappelle]

Life I'VE been grinding all.

[Teddy D]

Hello. Welcome to another episode of Club Shay Shay. I am your host, Shannon Sharpe. I'm also the proprietor of Club Shay Shay. And today we're at the brand new Villa 66 at Resorts World in Las Vegas. This is a spectacular two bedroom entertainment villa on the 66th floor with a stunning view of the strip. This is reserved for invited guests only, which I am. I'll be staying here tonight. The guy that's stopping by for conversation on the drink today is one of the most beloved comedians in the industry. He's had significant impact on the entertainment industry. He was on two of the greatest television shows in history, the Chappelle show and the Wire. He was honored also with the Red Fox Award. He's a critically acclaimed actor, a versatile performer, seasoned standup comedian, a host, a writer for over 30 years. He tours the world to sold out audiences everywhere. A fan favorite, a proud father, a larger than life personality. Here he is, ladies and gentlemen, Mr. Donnell Rollins.

[Dave Chappelle]

I really appreciate that introduction, but you missed one thing. What I missed R and B sing. That's got a hold on me lately. And I don't know myself anymore. And that's not the drink speaking, that's just me.

[Teddy D]

Yeah. Ladies and gentlemen, Mr. Teddy drowns.

[Dave Chappelle]

Oh, man. It's ironic that he's one of my favorite artists right now. And no black people swim. And I love Teddy's drinks.

[Teddy D]

Kenny's unbelievable.

[Dave Chappelle]

He's a good guy too, man.

[Teddy D]

He's unbelievable.

[Dave Chappelle]

And he swims. He swims in the milk.

[Teddy D]

Yeah.

[Dave Chappelle]

You know what that means, right?

[Teddy D]

No, I don't know what that means.

[Dave Chappelle]

All right. You know what bunny hopping is, right?

[Teddy D]

Yeah, I know what that is.

[Dave Chappelle]

Well, it's the opposite of bunny hopping. It's when a white guy dates a black chick, he swims in the milk. Which would be such a disapproval to Dr. Umar. But I put him on the chicken.

[Teddy D]

Oh, there you go.

[Dave Chappelle]

I'm just saying, son, some people don't appreciate love in all flavors. They used to call me Baskin Rawlins. Cause I dipped in different flavors. And I support happiness. I support happiness. That's what I. That's it. That's what people.

[Teddy D]

You don't like who like you.

[Dave Chappelle]

I like who like me.

[Teddy D]

There you go.

[Dave Chappelle]

There it is.

[Teddy D]

Mer, thanks for stopping by.

[Dave Chappelle]

I. Damn, boy, them bunnies sometimes bad nigga fall back. I'm just. I'm just saying. Lord have mercy.

[Teddy D]

I just want you silent.

[Dave Chappelle]

They don't talk a lot. Oh, man.

[Teddy D]

Sharon Sharp does not approve of this.

[Dave Chappelle]

Yes, you do. Yes, you do. Yes, you do. Don't be pulling.

[Teddy D]

Try to get. Come on, bro.

[Dave Chappelle]

Let's just say try to get me canceled. I try. Yo, if you ain't canceled by now, you won't get canceled. All right? Certain people, when you create, and this is the real stuff, when you create your own lane, when you're doing on your own terms, you are uncancelable, okay? And people always ask that question. You think somebody gonna cancel? People say to me, sometimes you think you're canceling? I'm like, first off, I'm not connected with a major network. I'm not connected with no corporate sponsors. So my only boss is the people that work hard, pay the money, come.

[Teddy D]

See me, come to you.

[Dave Chappelle]

And they can't cancel you for that.

[Teddy D]

Well, I do have. I am on television. I work for the guy that got the ears, right? I kinda wanna keep that little gig.

[Dave Chappelle]

I spoke on me. I didn't speak on you. And you said that your face looked like, ha ha ha ha ha. Yeah.

[Teddy D]

No, no, no.

[Dave Chappelle]

Like, you know what? He speaks for himself. I'm speaking for myself.

[Teddy D]

I did not approve the message that Mr. Rawlings delivered earlier. Thank you very much.

[Dave Chappelle]

Okay. All I've just said, be happy, bro.

[Teddy D]

Thanks for stopping by, man.

[Dave Chappelle]

You want to toast my mother? I talked to my mother, right? I said, I'm doing Shannon's show. She said, well, don't get crazy. And she told me, don't drink the yak. But I'm in a profession right now where I don't have any discipline. So to my mother, you have to get over it. She'll be all right. I love you, mom. It's a holiday just to see you as a 2B jolly.

[Teddy D]

Everything that you've done in the industry, continued success, bro. Thanks for stopping by.

[Dave Chappelle]

Thank you for help me. And, oh, my mother might have been right. That is smooth, though. You got the fancy sifters, too. Yeah, that's the next level I did.

[Teddy D]

We gonna send you home. We gonna send you a couple of bottles with you.

[Dave Chappelle]

Yeah, I saw Wiz Khalifa the other day. You could send me home with something else, too. I'm just saying, I didn't keep them. No people upstairs. He didn't keep anything.

[Teddy D]

I didn't keep anything, though.

[Dave Chappelle]

I was like, This I said, ooh, I'm coming back the week after. I said, it's still gonna be some remnants of it somewhere. Yes. You partake? What? I just want to say this. All the questions could be politically clear. You mean partake. Do I get high? Yes. Do I smoke? What? Do I smoke a fatty? In some cases I do. You do and I don't. But the thing is, I'm not. Like, some people, like, they smoke just to get lit. I like it. And then even my preference is, like, hybrids, heavier on the sativa side. Cause I like stuff that make me feel creative or make me want to write. But I don't like to, like, smoke a joint and just lay on a couch.

[Teddy D]

Yeah. Be spaced out.

[Dave Chappelle]

So you partake?

[Teddy D]

No, I don't.

[Dave Chappelle]

God damn. This gonna be chess. This gonna be chess.

[Teddy D]

You're from the dmv.

[Dave Chappelle]

Yes.

[Teddy D]

Quake. From the dmv.

[Dave Chappelle]

Yes.

[Teddy D]

Martin Lawrence, Wanda Sykes, Chappelle.

[Dave Chappelle]

Yes.

[Teddy D]

Tommy Davidson. What is in the water? What's in the soil? How do you get all these guys from that little one? Central location.

[Dave Chappelle]

I think you have that in different cities. Atlanta is a good market.

[Teddy D]

Chicago.

[Dave Chappelle]

Chicago's a good market. Joe Rogan has made Austin a good market. But I think that that crew of people, you miss a couple people, good friend of mine, my mentor, fat doctor.

[Teddy D]

Okay.

[Dave Chappelle]

It's just something about the people that we really believed in being good standups, okay? And we learned from, like, craftsmen, you know what I'm saying? Now today, you know, the comedy is going to a way where people go up there and ask, like, crowd work questions and everything. I don't think that that's the best form of standup, but it's getting paid. But when we was coming up, we came up. We came up behind Martin Lewis, Tommy Davidson. So we used to go to those shows. We wanted to be good, so we used to always sit in the back and study. The Young Comics Day, they don't do that. We used to sit in the back and study and watch. What makes this guy dope? What is he working on? How much time does he have? Is he good at some of the crowd work? Is he a good storyteller? So when you have people like that that you coming behind, you have no choice but to be a good comic, because you coming from coming behind some of the best people to do it. And everybody, every. And it's a funny thing you said. Everybody that you name on that list is still actively correct doing it. And we're talking, like, guys that have years, careers of 25 30, 40 years, still relevant and still making people laugh.

[Teddy D]

I noticed, and correct me if I'm wrong, I noticed a lot of the young and up and coming comedians, they lean heavily on the skits, and the older guys didn't really do a whole lot of skits. You got up there with a microphone, you had a stool and you told jokes, you walked the room, you appealed to the crowd. Do you notice the difference in how standup is being?

[Dave Chappelle]

I noticed a difference, but I will say it's evolved. And the reason why it was like that, we didn't have access to what the kids have today to blow up. I had a conversation with a young female comic maybe like seven years ago. She said, I'm a comedian. I was like, let me see some of your stuff. And she went to YouTube. She said, well, I do these skits. And I said, that's not being a comedian. She said, yes, it is. I said, no, it's not. But then she broke open the Webster dictionary definition. One who entertains a crowd with humor. So when I started, it wasn't the skit stuff. So when you say comedian, you only associated it with stand up now. Used to telling jokes, but now it's a whole different thing. The only thing, the, the thing about it is I'm like a real artist to this. I believe in it. And you see some of the younger guys, they get on real, real quick and you like. Well, I like them doing their skits, but not doing the standup. I just wish that some of them just would respect the art enough to take it a little bit more serious and want to be a craftsman of it. But when I, when I first started, if you wanted to get, if you wanted to get money. Yeah. And you wanted to give fame, you had to be good first.

[Teddy D]

Correct.

[Dave Chappelle]

You had to be good before the money came. You had to be good before the girls came. You had to be good before the fame came. But now you got somebody that can go viral real quick, don't have that skill set. So how do you tell a young, a younger comic, you know what? You need to work on this? And when he, he look at his YouTube and it's like this, 10 million. I just made 300,000 this week. I don't care about being good right now. I care about getting this money. But then you have some people that break away from it, that take the tools of being able to do this stuff on the Internet and also work on being good standups too.

[Teddy D]

But let me ask you this. When you're skit driven Is that sustainable? Because, I mean, now you can see some of you guys, some of you guys can also. You came up in the standup game where you told jokes, you work the room, but you can also do skits. But you believe if you start with skits first. Is that sustainable?

[Dave Chappelle]

It's sustainable because you're gonna get the money fast.

[Teddy D]

Okay.

[Dave Chappelle]

And at the end of the day, what are most people doing it for? For the cash. You don't have to do skits for 10 or 15 years. You got some of these guys to get a lick for two years, and if they invest their money right, do.

[Teddy D]

The right thing, they're good.

[Dave Chappelle]

But the funny thing, when I first started, I started as a standup, and then I realized that a lot of the jokes that I was doing was three dimensional. They was like characters, right? They had storylines. So. And I'm talking about maybe like 30 years ago. So I said, what I wanna do is take my jokes and make them characters. Them skits.

[Teddy D]

Yes.

[Dave Chappelle]

I had a sketch group years ago called Secret Society.

[Teddy D]

Okay.

[Dave Chappelle]

Red Grant was in that sketch group. I know. And he told me, everybody knew Shannon came to college, only had two shirts and two pairs of pants. That's what he said. And then he said. He also said back in. That's when he used to watch you wear his watch to tell time. But you say, so.

[Teddy D]

There you go.

[Dave Chappelle]

It's a hell different ball game now. Ocho. Ocho, I'm telling you, man, I had a nice fake coat. Yeah, I know, I know. And you rocked out. You made me feel, you know, smoke. What was the question again?

[Teddy D]

The end of sustainability with sketch.

[Dave Chappelle]

Oh, I had a schedule. It was me, Red Grant, it was Mike Epps. It was Just Got Rich Perez. It was a whole bunch of us. And we was doing sketch back then. We was a hell of a game before the Chappelle show even existed. I had to. I looked into the future. I was like, all right, I'm gonna bring this super group together. It was like 12 of us. And I knew the group wasn't gonna last long because anytime you got 12 different personalities, it's always gon.

[Teddy D]

That's a lot.

[Dave Chappelle]

It's always gonna change. But what I realized, it almost. I felt like it was like Wu Tang of sketch. I was like. I knew we wasn't gonna all stay together. I knew that we had people that kind of were stronger on the producer side, stronger on the writing side and the acting side. In fact, my manager at the time, she said, donnell, I think that group is about to Fall apart. And I was like, it's designed to fall apart. But if it wasn't for us to come together like this, we wouldn't have had the platform for people to see what to do. But you can sustain a career with just doing sketches. Cause people are coming out just for that. Not in a million years when I thought somebody could make millions of dollars in tour theaters, just sitting on a stage, having a podcast and talking. So comedy, the way it's perceived and how you can make it work for you, it's evolved where it's so many different lanes open now.

[Teddy D]

When I think of comics in the past compared to today's comics, you guys, they had a seedy past. They've had a very like, you look at Prior, you hear Ms. Pat tell her story, and she's almost like an old school comic. The heartbreak and the disappointment that she's had and what a comic is able to do, they're really able to take true events and make them funny. And that's how they're able to get over the trauma and the hurt and the pain that they're dealing with. Do you notice that, that the comics today are a lot different? Their past path is a lot different than you guys to get there.

[Dave Chappelle]

Yeah, I think that. I don't want to say it's easier, but you have different avenues.

[Teddy D]

Okay.

[Dave Chappelle]

When I came up first off on the stand up side, it was almost impossible to be seen as a black comic because you only had a couple of network. You had the David Letterman show, Johnny Carson. I'm talking about way back in the day.

[Teddy D]

Yeah, right.

[Dave Chappelle]

And then if you look at the list of comics they used to do that, it was all white comics. You might have one black comic every couple of years. That's why it was a good thing that Def Comedy Jam came because there was a group of comics. It was a chitlin circuit, it was underground, but they weren't being seen. But I think that now your phone man, I tell anybody your phone can just blow you up. And everybody in this business, they make excuses. But at the end of the day, you can have a little bit of talent, but if you got the right work ethics, you can make it happen for yourself. When I started here, abc, CBS and NBC, hbo, we give a special every two years. But how many people got an opportunity at. So the people that sit back and complain about what they can't do. My dad told me a long time ago, you got two excuses, a good excuse and a bad excuse. And in the day, your success is dependent on how hard you work and you can get it. It's too many examples of that. Get it with the right work ethics.

[Teddy D]

Would you consider D.C. the funniest city you mentioned? New York you mentioned. But when you look at per capita, you look at the DMV and how small it is compared to a Chicago, compared to a New York and some of these other major cities, everybody got.

[Dave Chappelle]

Their bosses, everybody got these people. But I think pound for pound, the Pound for pound, D.C. is one of the best cities that's had comics that not just got hot for a minute, been able to sustain itself in this business.

[Teddy D]

Yeah, man.

[Dave Chappelle]

And a lot of people can make arguments without Chicago. It's a lot of good comics that come out of there. When you talk about the people that's been on the small screen, the big screen, it has success, just touring. I think hands down DC is one of the best, one of the best.

[Teddy D]

Series we look at Martin been on television and in the movies, you look at Dave Chappelle, television and movies. Tommy Davidson, television and movies. Wanda Sacks, television and movie, Donnell. When you got into this, because you see the transition. You see, you see Richard Pryor was a stand up, did television. Eddie Murphy stand up, did television. Is that the natural progression does most. I can't say all. Kevin Hart can't say all. There's no such thing as all and every. But do a lot of comedians get in to stand up with the hopes and dreams aspir of doing television?

[Dave Chappelle]

I. I think a lot of them that's the ultimate goal.

[Teddy D]

Okay.

[Dave Chappelle]

But I also think that at the end of the day, and I look at my career, you know, whether I do another film project or do another television project, I've at least positioned myself where I can put my name on the marquee and make some good money for the rest of my life.

[Teddy D]

Okay.

[Dave Chappelle]

You know, I think that that's an evolution for some people, but not all people. And some people it was like the standup was just the platform and the setup to be an actor. Chris Tucker, When Chris Tucker first started, everybody knew when Chris Tucker first started, he probably had 10 minutes of fire set, you know what I'm saying? But when you saw Chris Tucker perform Def Jam, when he came out, just pissed off, man, I'm so broke. If a robbed me, it'll just be practice. You knew you wasn't just looking at a stand up, you was looking at a movie star, you know what I'm saying? He was one of those guys. And Martin Lawrence is a great stand up. But when you look at Martin Lawrence, you could see him in his television show, you can see him in a movie. But for everybody, it doesn't work out like that. Everybody have Some people don't care to be film tv. They just want to be able to make an honest living doing something they love. And how many professions or how many people get an opportunity to actually call their own shots? They are their own boss, do what they want to do and make a good living. Not too many, right? And it's not to Even if you look at the era, the Def Jam area, the era of all the comedians with the nicknames and everything, I would say out of everybody performing Def jam, it's probably 5 or 10% of those people that are actively working this people will still go pay ticket price to.

[Teddy D]

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[Donnell Rawlings]

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[Teddy D]

You kind of got your breakout. You worked on a show, and many consider this show as the greatest. One of the greatest TV shows, if not the greatest. The Wire based In Baltimore.

[Dave Chappelle]

Yeah.

[Teddy D]

How did that role come about?

[Dave Chappelle]

The crazy thing, if you really a historian on the Wire and David Simon, the Baltimore area, you know that Charles Dutton had a miniseries called the Corner. The Corner was before the Wire. And my relationship with the Wire was I played Bread on the Corner, heroin addict on that show. And David Simon, if you'd watch any show that he's produced, or Zach he's produced or he's written, he is really loyal to people that worked with him before. So that kind of gave me a heads up on the opportunity to be on the Wire. But the crazy thing about the Wire was the role of Omar. It came down to me and Michael on that role of Omar, right? Robert Colesberry, one of the executive producers of the Wire, who's not there anymore. When I came on set, he said, you know, we had you heavily favored to play the role of Omar, right? I had no idea that he said, but this character, Dae D Price, we thought there was gonna be something special. We wanted to save you for this role. And if you really follow Wire, you notice a lot of people say first season was all about the towers. Stringer Bear, Aegis Elba, you know, Wood and all those guys. The second season, it made a twist. It went from the towers to the docks about being at the shipyard. And that was because the Baltimore tourism board was complaining that every time that they have a show that's in Baltimore is always depicted as being a seedy drug written. And I'm like, when the last time you walked downtown, that's what the fuck it is.

[Teddy D]

They lied.

[Dave Chappelle]

They called it body more. They don't call it for no reason. So they had to switch. Cause my character, Senator Clay Davis ASSISTANT I got caught with $30,000, right? I had to give it back. And the next season, my character wasn't in the story arc. So once they switched it to the docs, my character got lost to David Simon, who's really loyal to people that's on that show. He wanted to play like homage to my character. He brought me back. But that was an amazing experience to be on that show.

[Teddy D]

The role that you played, how easy was it for you to play that role?

[Dave Chappelle]

Clay Davis? No role is easy for me to play because I'm more connected to stand up than acting, right? And to be quite honest, half the time I don't even know what the I'm doing. You know, it was one scene Magnolte, he was one of the actors in the Wire. He was a director too. So it was one scene When I had to snitch on Clay Davis, right? And I was feeling uncomfortable doing it, I was like, what type of. What emotion do I want to have? So I was playing it, like, kind of nervous, like, oh, no. And then he came up to me with his accent. He was like, I don't know if you're playing it right. He said, I think you really want to put this guy down. You want to lock him up. I said, motherfucker, I don't know where you from, but where I'm from, you don't snitch. Yeah, and you don't snitch. Like, he's a jolly good fellow. You don't be like, oh, it's that guy. Put him away. You got to act like that's the hardest shit in the world. You're like, ah, man, I really don't want to snitch, but I don't want to go to jail as much as I don't want to snitch. And then after I did that, he was like, okay, I think you might be bloody right. And then he let it stay. Yep. But that show, man, even though it was so interesting, because in acting, I never took a class. I'd never been trained. The furthest thing, the most training I've ever done was I got a monologue book, and I used to practice in a myriad of different monologues. And the crazy thing was, even when I got the roll of bread on the corner, I had no idea how that happened, right? I was in an audition for, like, 30 minutes. And the casting director, Jackie Brown, Carmen. She was one of the biggest black cast directors in New York. I was eating in this audition, and I wanted to be like, all right, whatever. And she said, down the hill, God is in the room. You good? Take your time. I was like, well, God, you need to come right now. I did the audition, and I didn't think anything. I said, that's past me. And I booked the role. And when I went on set, the first thing I asked Dave was Simon. I said, how did y'all pick me? I was like, I really thought I bombed that role. I didn't know what was going on. And he said, donnell, we like the fact that you threw the lines away and you did your own thing. The reason why I threw the lines away. Cause I didn't remember the lines. Yo, I ain't throw shit away. I ain't throwing away. I ain't know it. I ain't know what the hell was going on. So. And then another thing. Cause I was Playing a heroin addict?

[Teddy D]

Yes.

[Dave Chappelle]

And I think that everybody. And I don't be reading my scripts like I supposed to. Everybody looked at that character as a heroin addict. And I'm pretty sure everybody went in there with the stereotype of leaning like the dope fiend and everything. And I didn't do that because I didn't know. I just thought it was a cool dude, right? And what they wanted to see was, who was this guy when he wasn't high? Was he that funny guy in the neighborhood if he wasn't high? So, you know, I guess God was in the room. I got that part. I built a relationship with those people of hbo, and it led to me being on the Wire.

[Teddy D]

When you were doing the Wire, did you realize it was gonna be so well received and it would be the phenomenon that it became?

[Dave Chappelle]

I didn't. I didn't. I had no idea. But what I did know, I was doing shit nobody else was doing.

[Teddy D]

Right.

[Dave Chappelle]

You know, I was a Def Jam comic at that time. I probably was one of the only comics that was on Def Comedy Jam and then on a critically acclaimed show, right? I didn't predict it. I didn't predict it to be that big, but it just took on a life of its own. I mean, Idris Elba, you know, came from working the door at Caroline's Comedy Club in New York City to being one of the biggest stars in the country. And I gotta tell you something, I hated that when he was on the show. And the reason why, because they had these women called a string of ballettes or something. He had fans everywhere, right? And then I would meet girls and they were like, what's you on the Wire? And I thought it was my time to shine, right? They be like, yeah. They be like, could you introduce us to Stringer Bell? I was like, you and Stringer Bell, Right? But when they killed him, I was like, yeah, where your man at now? He dead.

[Teddy D]

How you celebrate the man getting killed off, man?

[Dave Chappelle]

Cause he was taking all the girls. And I was so happy. He just really doubled down and came one of the biggest international stars in the world. So he won that fight.

[Teddy D]

Yeah, he's out back.

[Dave Chappelle]

But it was Yo, Wood, all of those guys, man. And we had, like, a dope unit. Like, I was still doing stand up then. And can you imagine? I would do, like, a little Hole in the Wall spot in Brooklyn and have half the cast of the Wires show up. It was crazy. But nobody knew how big that show would be and how it lasted long. We talking about there Was an article Entertainment Weekly. And they said Two of the Days had 100 best shows in the history of TV. And Chappelle's show in the Wire ranked. And I was like, you ask yourself, legacy, what people remember you by, if nothing else. If I'm not a part of anything else, at least I could say I was a part of what people are gonna talk about. They're gonna be talking about their shows until the end of time.

[Teddy D]

Yeah. In 100 year history of television, I've been on two of the biggest shows they might remember.

[Dave Chappelle]

Part of Def Jam, but those shows they remember. And I was doing both of them at the same time. At the same time, yeah.

[Teddy D]

What do you remember about Idris? Because that was early in his career also. So he was just an up and comer just like yourself.

[Dave Chappelle]

I remember he took all the damn girls. That's what I mean. Yo, I'm still. That's all you cared about. I'm still traumatized. And then he would double down with that punk ass English accent. You want to go to the Blood E Hotel? And I got a New York yo, son. Y'all tried to go. It was a whole different thing. But I say one of the most humble guys and people don't understand. They hear about him DJing whatever. I think Idris was, and still to this day is as passionate about DJing is as he is as an actor.

[Teddy D]

Really?

[Dave Chappelle]

Yeah. Oh, 100%. Oh, he takes the DJ super serious.

[Teddy D]

Wow.

[Dave Chappelle]

Yeah.

[Teddy D]

So when you first heard that accent, did you like, Bro, you. I saw you at Caroline's Comedy Club. Bro, you. That ain't your. You don't talk like that.

[Dave Chappelle]

When I first heard the accent, I wanted to keep talking. Cause I wanted to use it. Oh, you was that. I wanted somebody to come to the bloody hotel too. I wanted somebody to come to the Bloy Hotel. I'm like, oh, man, he tall, dark, handsome, and an accent. I ain't got a chance, son. And I was just starting my ashy journey at that time. So it was. I was out of the. I was out of the loop.

[Teddy D]

But if you think about it, if you go back, you look at Idris and the role that he played, and you look at Damson Idris in Snowfall. How do the British actors getting all these gangster roles?

[Dave Chappelle]

I mean, they. They students of the craft. I know there's been some talk, like to get on the road, but you gotta be. Just imagine the level you have to be. All those guys, they gotta get dialect coaches.

[Teddy D]

Yeah. Cause I didn't even know I didn't know the guy at Snowfall. I did not know he was British.

[Dave Chappelle]

No, I couldn't tell. I don't know if they working for a cheaper amount of money. I don't know if they're the low that part of it. But for you to be able to embody these characters and to do it out in another accent, there's gotta be something to be said about their skillset. But at the end of the day, we complain about everything. But at the end of the made the best man win, right? You know.

[Teddy D]

Cause a lot of people, they're getting upset, like, hold on, you got black actors, actors right here in America. And then you bring British actors to play a black person, A black American, right? Why not just hire a black American to play a.

[Dave Chappelle]

Because they might not have been the best person for the job. Okay? I don't understand. This business is about competition, right? And like what you saying? Like people complain. I know this may sound crazy. Work harder, everything ain't gonna be for you. You gotta keep going. This whole notion, man, first off, Hollywood is up, okay? It's up. People's perception of it is different. At the end of the day, all a lot of people do is sit back and complain. I say, pull yourself up by the bootstraps, work harder. If you didn't get that role, keep going. This field is a job where you going to be rejected 95% of the time. This is a job where you're going to be broke most of the time. When people come up to me like Donnell, you got any advice or words of wisdom? I always tell them, you first off, you got to be able to be happy being broke in this business. If you can't be happy being broke, you might as well get out of it. Cause you're going to be broke most of the time you're doing it. If you could find a happy place, if you could. And I say, in my case, when I first started, wasn't making no money. When I do a get for $30 and get a five pound bag of potatoes, some bologna, some cheese and some eggs, I'm like, I got food for the rest of the week. I was happy because I knew if I keep on, eventually it's gonna pop, right? And every, not everybody, but for the most part, you're gonna get a shot, you're gonna get in the game. But what you do with it when you get in the game, and that's what's gonna separate you from everybody else. To sit back complaining, not doing nothing and looking at everybody succeed and complain about NFL playoffs.

[Teddy D]

We're talking about the NFL playoffs. You bet. We are. Get in on the action at DraftKings Sportsbook, an official sports betting partner of the NFL. Scoring Touchdown is key to winning in the NFL playoffs, and the key to you scoring big is betting on them at DraftKings, the number one place to bet touchdowns. Ready to place your first bet? Try betting on something simple like a player to score six. Go to DraftKingsportsbook app and make your pick. Here's another reason to watch your favorite player crush it in the playoffs. New customers bet $5 and get $200 in bonus bets instantly. Score big during the NFL playoffs with DraftKings sportsbook. Download the Draft King Sportsbook app. Use Code Shannon. That's Code Shannon for new customers to get $200 in bonus bets instantly. When you bet just five bucks only on DraftKings sportsbook, the crown is yours.

[Donnell Rawlings]

Gambling Problem Call 1-800- gambler in New York, call 877-8-HOPE NY or text hopeny467-369 in Connecticut. Help is available for problem gambling. Call 888-789-7777 or visit ccpg.org Please play responsibly on behalf of Boot Hill casino and resort, Kansas 21. Age and eligibility varies by jurisdiction. Void in Ontario, new customers only. Bonus bets expire 168 hours after issuance. For additional terms and responsible gaming resources, see DKNG Co Audio when it's tip off time at my house, there are a few things that are must haves on my checklist. My fellow friends and fans. Check. My favorite jersey. Check. An iconic drink that's a fan favorite? Check. Hypnotic can turn any cocktail into an iconic creation. With its game changing color and tropical flavor, Hypnotic should be in everyone's starting. 5 I consider hypnotic the point guard of my game day roster because not only is it versatile, like having it on the rocks or as a base for cocktails, it also finishes smooth and just like the banners in my stadium, letting people know that we take championships seriously. Having Hypnotic at my watch parties lets people know that I also take quality seriously since it's crafted with high quality ingredients for a championship level drinking experience. So the next time you need a break from the action with a distinctive timeout, look no further. Grab a bottle of Hypnotic and make your next basketball watch party iconic. Enjoy the vibrant taste with friends and turn every game into a memorable celebration. Hypnotic where every sip is a slam dunk. Hypnotic Liqueur Bardstown, Kentucky 17% Alcohol by volume Hypnotic reminds You to think wisely, drink wisely.

[Shannon Sharpe]

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[Teddy D]

When you became successful, you did the Wire, you did the Chappelle Show. You're still doing your stuff.

[Dave Chappelle]

I wasn't successful then. I was working. I was successful. That's the illusion people have about tv.

[Teddy D]

They think when you. Everybody making big dollars, though.

[Dave Chappelle]

Yeah, good.

[Teddy D]

You ain't.

[Dave Chappelle]

Let me tell you something, man. When I was doing Chappelle's show, and the thing about it was, you heard me say I'm rich, bitch, at the end of her show, right?

[Teddy D]

You are rich, yo.

[Dave Chappelle]

I was rich, yo. I go to restaurants that bill would come, they would be like, just, uh, we thought you was rich, bitch. I said, I'm n. But at the same time, Shannon, I knew I was positioning myself for success when I was doing Chappelle's show. And I seen people come on this platform. That's what I don't understand about actors and people. You signed the contract.

[Teddy D]

Yes.

[Dave Chappelle]

You put your name on the dotted line.

[Teddy D]

Right.

[Dave Chappelle]

You started this show. It was a small show. It just so happened that the show blew up.

[Teddy D]

Right?

[Dave Chappelle]

Right. Your contract already signed, so you entitled to all that money. No. The only person in the history of this business has ever really tested the industry and said, you know what? I know I did do a up contract, but I know my value is. And y'all still gonna step up. Dave Chappelle, Right. The only one, he forced the hand of Commerce Central. And I think it was very admirable what Commie Central did. Cause they could have said, man, you. This is what we supposed to pay you. But, you know, when I was doing Chappelle Show, I was making $500 a sketch. And people already know. The blogs were like, oh, they should have. But the show wasn't established. I knew the best thing I could do that was just standard. That's what you got as an actor. But I knew me working that episode, me getting three minutes of camera time, now I could go out and get my money on the road.

[Teddy D]

Right.

[Dave Chappelle]

Even when we. When we was Working that first year, me, Charlie, nobody on that show was making a lot of money. But I was like, wait a minute, this don't match up. Everywhere we go, we hearing I'm Rick James, bitch and everything, right? We know we popping, but our bank accounts ain't popping. And I was like, we gotta do something. I came up with the idea. I said, we need to do a tour. I said, let's do a tour called I'm rich bitch tour, right? And at that time, I forget the name of the agency, but it was a young agent named Mike Berkowitz, right? He was a very young agent. My manager brought to him. I said, I want to do this tour, Charlie, name is popping. It was nowhere you go. You didn't hear Charlie Murphy. Charlie Murphy never did comedy before, which I found very strange to be around all these people, but never tested yourself. So I said, if I want to do this tour, I gotta get. I'm the first person ever took Charlie Murphy on stage. And I bullied him to do it because Charlie, man is a funny guy. Talk a lot of trash. And then what happened? Whenever I wanted to shut him, I was like, yeah, you tough in the streets, but put a microphone in your face and see what happened. I knew we was trying to get some money. He did his first open mic. All I needed him to do was have 10 minutes. Bill Burr at the time, Bill Burr. And there's no disrespect because you see what happened to Bill Burr career. At the time, Bill Burr probably was a comedian, was headlining, probably $1,000 a weekend. And I'm not saying no disrespect, but you knew when anytime somebody saw Bill Burr, you know he was going to pop. But that's just where he was then. And I said, okay, I get Charlie to do 10 minutes, I bring Bill Burr on the show. And Bill Burr wasn't a draw, but he was a funny act. And I said, we're going to do this tour. Yes. I could put anybody else on the tour, give them a little bit of money. But I said, no, we want to go get some money. Three way split. And we did the On Rich bitch tour. And we made some, probably at that time in our career, the most money you'd ever made. Most money we ever made. But with anything, Charlie started to know what his value was in regard to people wanting to pay to see him. Bill Burr was buzzing. He knew that he was about to take off, but we had to make adjustments. That 500 episode was getting us thousands of dollars on the Weekend. And that was the week at that time, that was the most money any of us have ever seen.

[Teddy D]

Right, Bill, was he the first white comic that you actually. That you went on tour with?

[Dave Chappelle]

Yeah, but Bill Burr, his story was like, you know, Bill Burr, when he came to New York, he was one of the few white comics that did every room. He did the mainstream room, and then he did the Chitlin Circus. And I think part of his. You know, he's a very powerful, strong comic. Yeah. But I think he got a lot of edge being able to go into those rooms that everybody feared and just take control of it. But Bill Burr's always been a.

[Teddy D]

How difficult is that when you're young, you're a black comedian? Because I've always asked, and I ask this a lot of times, do you set. Do you write a set? Like, I'm gonna be in a predominantly white audience. Do I write a set accordingly? I'm gonna be in front of a predominantly black audience. Do I write a set accordingly? How difficult is that to do when you're young and up and coming? Obviously, once you get established, you can go into any room.

[Dave Chappelle]

It's the toughest thing, because usually when you first start, Shannon, you write, your voice is usually who you perform for.

[Teddy D]

Right.

[Dave Chappelle]

So if I do the Chitlin circuit, it's easy for me to go up there. The way I speak, certain things that I say, I already know they're gonna understand it, but then you have to. And even with me helping with my accent from D.C. coming to New York, you know, I was going places, and people's like, what? What did you say? Certain rooms, it wasn't that way. Other rooms. I said, you know what? You gotta work on your addiction. You gotta enunciate and you gotta do this. But. But a lot of comics, they get used to one circuit or one side of it, and stay with that. But always. Always knew that I wanted to do more than just the Chitlin circuit. I wanted to do more than just what the black comics. And my thing was I wanted to be. When I was in New York, there was a very popular club called the Comedy Cellar. It's like the biggest comedy club in the world, the biggest names. And when I was in New York at the time, it was only two or three black comics working here. It was Keith Robinson, it was Dave Chappelle, Greer Barnes, and Will William Stevenson. That was it. And it basically is like you walk around the corner, the black club and the white club. It wasn't too many people doing both. And I said to myself, if I'm going to be respected in this business or if I want to be. Want to be one of the best to do it, then I want my name to be on the same line out as the best to do it. And that was one of the reasons why I said I wanted to do mainstream. Because the black circuit back then, they was paying more.

[Teddy D]

Right.

[Dave Chappelle]

But you didn't really have no future. And at the end of the day, you was just getting pussy in a check, and it wasn't even a big check.

[Teddy D]

But for you, you'd realize that in order for me to be what I want to become, I'm going to have to have crossover appeal. I'm going to have to go appeal to that wider.

[Dave Chappelle]

I got to go where people are gonna see you back then, producers and directors and executive producers. They wasn't going. They weren't going to Chocolate Sunday. They wasn't going to the Boston Comedy Club Sunday night. They wasn't going there. So if you wanted to be seen, you had to cross over. Or another thing people used to do, they got. People used to get caught up in the fame of it, in the women, in the money. I'm cool with this. But as the years go on, you like this. I wasted so much time just catering to this side of it when I could have been over here. That's one of the things. Like, I hear people talk about Kevin Hart all the time. Kevin Hart was smart enough, and I'm not here to defend anybody. And you know something about your couch, you be wondering when it's going to heat up. Right. And I know deep down them cards is going to get crazy. That's a lot of cards. Right. I'm looking at him like this. He got me with that. So when you was growing up, what inspired you? I wave you like this. So when you. And so. And so was me for now. But. But what people don't know, and I'm using, and I, not Kevin Hart, don't need me to defend him. I know this little work ethics.

[Teddy D]

Yes.

[Dave Chappelle]

Because I was a part of it. I said, it's another platform. I remember Kevin Hart had one joke, and this is not being racist. He's doing an impression of a monkey. Right?

[Teddy D]

Right.

[Dave Chappelle]

And he was the best monkey you ever seen do a monkey joke. He had. I mean, he had this going on everything. And he used to riff and he used to work the grimiest spots, but he used to commute from Philly. He would come up, he would do my clubs, the hood clubs, those $50 spots and then he'd go do the mainstream spots. He knew that this is only gonna get me one thing. He had a bigger picture. He knew exactly what he was gonna do. He knew how he's gonna get there. You want representation, guess what? They're not going to the Chicken Factory. They're going to the Cellar. They're going to the Communist Strip, they're going to that. And you have to have the work ethics to sit around Shannon and wait for opportunity. Somebody fall out on the lineup, Right? Somebody you gotta get a reference to. Somebody just sit around, just hanging out one day. Okay, now's your shot to go in here. And I've seen him do that. I've seen him go from my spots to the comedy seller spots. I seen him get a manager. I seen him go to one of the most prestigious comedy festivals. It's a comedy festival. Shout out to my man Bruce. I ran JFL Comedy Festival for years. This festival, 25 years ago in Toronto. Montreal.

[Teddy D]

Montreal. I was being Kennedy. Yes.

[Dave Chappelle]

This was everybody's dream. If I could get on there, guess what? You not going to get on there. In a chilling circuit. You're not. There's no way. Some kind of way. You got to get into the audition. You got to mainstream. But one thing about that special, it broke so many people, that festival. Monique, Uptown Comedy Club, it broke her. This festival was so dope, Shannon. You can go up there with an eight minute showcase set, nine or ten minutes, and if you got a point of view, people could see what they could do. You walking out of there, people was walking out there with a quarter million dollar deal just to hold you. That's what that festival was. And when people don't understand, they say, well, how did so and so go from this to that to that? You missed the whole. The reason why you missed it because you wasn't invited, you didn't have to audition. And you can't knock a person that knows how to use their resources and position itself for the right people to see it. Or you could bitch, complain, do them chitlin circus shit all you want. They pay money. That's where I came from. But eventually you got to figure out how to maneuver yourself through this business. Kevin blew up off of that, Dave Chappelle blew up off of that. Sue Costello, Monique. It was so many people. It was the hottest festival. And that's what the birth of Kevin Hart was for. The people like, oh, it's. Oh, he's a plant. No, his path was different from your path. You cannot Fault anybody. Because the way they get it is different from way you get it. And all of this bullshit about, oh, I came through the mud, so and so. Guess what? I came through the mud. Guess what, Shannon? I took a shower. I put cologne on the day. I washed myself. I used my wash to let you know how much time, and I switched it up. And there's nothing wrong with it.

[Teddy D]

When you started having success, did people think you took the easy way out? Because it seems to be. I get that now. Oh, he sold his soul.

[Dave Chappelle]

But guess what? They don't know what the Prince say. Sometimes it takes 10 years to be an overnight success. Those people that just introduced you, they don't know. But the real people, they know. That's why I've had arguments with comics or whatever. Oh, he ain't so and so. I'm like, ask somebody about me. Ask somebody about my career. Oh, it's easy. You got the suits. Ask somebody about me moving from D.C. sleeping on my Royal Watkins couch for a year and a half. He get a TV show, leave me in his apartment. I ain't got no money, no electricity, no water.

[Teddy D]

You ain't paying the bills, huh?

[Dave Chappelle]

I tried to pay the bills. Them $30 shows wasn't getting it, yo. I had an African landlord, too, and he's so sick of me, man. We used to pay him what I owe, I owe. He was so mad. He said, please, I would pay you to leave, yo. Cause it was an area about to be gentrified. He was like, please, no, no. I don't want nothing. Want you to leave. I'm talking about a stitch, of course. My man's apartment up, up top, sliding down. Switching that Stitch Accord from a hot plate to an iron to a heater. People don't know. Nobody knows your comeback other than the people there. But then at some point, it ain't your job to give a.

[Teddy D]

You know, Because a lot of times, all they see is the success. But they never see the struggle. And because they didn't see the struggle, they see the success. They see the TV shows, they see the cars, they see the house. They see whatever.

[Dave Chappelle]

That's what everybody want to do now. They want to be you. Everybody want to be you today, right? Everybody want to be Joe Rogan today, right? Nobody want to be Joe Rogan 25 years ago, when people was like, what the is this? But now they see success. They want to do it. You don't even know how many they say, now. I'm gonna do a podcast. I want to do a club Shay. Shay. They don't know how many years you was putting in when nobody believed in this, Right? When you was like, watch, it's gonna pop if I keep going. I had offers to do this show, people trying to flip and this before it popped. And I feel bad. Not feel bad coming on the down, because I didn't. I didn't. I really didn't want it to feel like, oh, now it's popping always. But it was always a conflict. Another one of the reasons. Cause we got mutual friends. Red Gramp, my man. Keith Burns was one of your. Okay. Yeah. I went to. I grew up. I've known him since we played little league football together. Right. But going back to my point, everybody wants to take the easy route. Nobody wants to take the hard work. It takes something like this. It wasn't last year. No, it takes years. It takes years of looking at those subscriptions. God damn, I thought that was gonna pop like a thousand views.

[Teddy D]

You don't know.

[Dave Chappelle]

You don't know. But then when that lick hits, you feel good. But everybody else like, oh, my God. But you back there like this, I knew it, right? All I needed was the time.

[Teddy D]

You go back to the wire yourself. Idris Elba, you had. Michael B. Jordan was on there. I think he was like 14, 15 years of age.

[Dave Chappelle]

Yeah.

[Teddy D]

Michael K. Williams. I mean, that cast that you guys had, what was your. Did you have a relationship? Were you guys ever sat together?

[Dave Chappelle]

I had a relationship with Idris Wood. I had a relationship with him. Michael B. Jordan. I was like, so much older than him. I really had nothing in common with him. Michael K. Williams. We was really, really close. That was like one of my closest guys. Connected to that. He used to come out. He was a real Brooklyn, Brooklyn dude. So he used to be like, man, rip to him. He's a great dude. Troublesomes, things happen. But he was one of my closest connections, but the biggest connection. And I wanna go back when I did the Corner. Tasha Smith.

[Teddy D]

Okay?

[Dave Chappelle]

Tasha Smith and Candy Alexander.

[Teddy D]

Right?

[Dave Chappelle]

Tasha Smith. And I don't wanna be offensive or anything when I say this. People don't take the wrong way. She's a bad bitch. And when I say that, not just on the acting side, I'm talking about directing. There is nothing she can't do. A lot of people don't know. I'm trying to encourage her to go back. She started as a standup, but she was my coach when I didn't know what I was doing. Channing and I don't have you talking about a Guy with no training, right? She used to pull me to the side, read my lines with me. In fact, she was a reason why I was on bmf. Wow. She was like. She called me one day. You know how certain people call you? You know, it's a money phone call, right? And I was in the. I was getting dressed for another thing. It was for Winning Time, the HBO show.

[Teddy D]

Yeah.

[Dave Chappelle]

By the Laker Dynasty. And I'm all happy. I'm like, I'm working. And I get a call for her. I'm like, I ain't got time to answer this call. I'm getting dressed, right? Soon as I picked the phone up. Because she said, when I call, you better answer that goddamn phone. I'm with 50 right now. I'm with Randy. Randy was the creator. And she basically gave me that role. Wow. That role I played. What was that? Alvin? She gave me that role. And this is what people don't understand about this business. Everybody always wants to say, oh, you had that little role, or that little so and so.

[Teddy D]

Because they didn't have it.

[Dave Chappelle]

No, not only that, because they didn't have it, but only that. They don't. They don't look at what. What you building, right? First off, I tell anybody, you got to get on set first. You got to get on set. Oh, I'm going to turn it there. I only got one line. You got to get on set. That role that I played, I was only supposed to be in one scene. Season finale. Randy loved that character so much. Cause it was based on one of his cousins. He was really connected with that. I was supposed to be on one episode, right. The next. They brought me back, and they fell in love with the character. They brought me back another episode, another episode, another episode where it went through that second season. I think I was in seven out of the. Out of the. Out of the ten. And that's because I took that little as role and I. And I did the parlay. Yes, I do Chappelle Show. I was not supposed to be on that show. There was no cast. Everybody call us the cast. It was no cast. It was. Dave and Neil had this show, right? And they could just put anybody on the show they wanted. At the beginning, we had one actor in one scene. I remember he wasn't doing well. Wasted about an hour and a half of industry time, a lot of money. And where Dave and Neal would just say, you want a show? They said, you know what? Comedy Central says that everybody has to audition now. I had already did. I'm rich. Bishop, right? I could have been like, man, y'all know my work. I'm not auditioning. But I said, if I do that, guess what? I won't have a shot. So I went back in the audition room, murdered the audition. Never heard that again. But I was only as good as my last sketch. I was only as good as my last scene. It wasn't like they had to write stuff for me. And my thing was, if you go hard enough, one thing when you want a set, if you start ripping, same thing I say with Jaleel White, with Urk. Supposed to been in one episode. But if you rip and them writers now, they start thinking about you now. They used to just like, okay, we gonna bring them in. Another thing, when I was doing Chappelle Show, 90% of the things I was in, I wasn't supposed to be in. I was broke. I knew that if I go on set, I get some free food, I get to hang out, and they gonna tap me in.

[Teddy D]

Right?

[Dave Chappelle]

Like, 85% of the things that came out of my mouth on that show, it was all improv and me being in the moment, just hanging out.

[Teddy D]

I think you mentioned that you were supposed to have Michael K. Williams role, and you see what that role became. Did you like, damn. Think about what could have been?

[Dave Chappelle]

No. The reason why, because certain things happened. I was like, they got the best person for the job. And another reason why they had the best person for a job, for the job with him. Cause I wasn't gonna tongue get some big old. They got the right one for that one. I was like, I just thought he was a gangster. I ain't know he was taking dicks, son. But that's. They wrote that in. I didn't write it in, but I was like, you know what? They got the best person for that job, right? Another situation. There's a role. Katt Williams was here, right? Right.

[Teddy D]

Yeah.

[Dave Chappelle]

He talked that role that he played, Alligator man on Atlanta. That role came to me and him, right. I was still in the running for that. I was ash. They said, you still. And you said, I ain't saying I was going to get the job.

[Teddy D]

Right.

[Dave Chappelle]

But I knew I was still in the running for it. But certain times I look at people, I look at their skill set, and after the minute I found out that Cat Williams got it, I was not mad that you didn't get it. I didn't get it. I know how strong he is as a comic. I know how strong as an actor. That role, I looked at the role and the Dynamic of it. And I know he would go all in. And I was absolutely right about they was a bad choice. Cause he won an Emmy off with that role. But never once that I was envious or jealous. I was like, back to the drawing board.

[Teddy D]

I remember when Michael K. Williams said that he was scared. He was conflicted about taking the role. And we hear now a lot of about blacks putting on dresses, playing those type of roles. Where are you on that? Where are you on that?

[Dave Chappelle]

Danielle, I will tell you this, and you might edit this out. Need something to be mad about. And I hope you can keep that. Are not happy unless they mad about something. How many? It's rich bitter out here. They got everything. Still have something to be mad about. You can make that argument. Oh, the demasculation of a man. Whatever. You know who you are, right? And really the reason why that's so stupid to me. Flip Wilson. Geraldine Flip Wilson. All right. This motherfucker wore a dress. Guess what? He was owner of his show. He was executive producer. And he knew who he was, and he knew he was a character. And I'll tell you another thing. They always talk about his dress. Shit, right? I'm gonna tell you when I was like. And I'm not saying, you know, I know they be like, oh, that means he would put a dress on. Outta here. Ving Rhames played Holiday Heart.

[Teddy D]

Right?

[Dave Chappelle]

Right. Transgender. I hope I'm getting it right. Character Holiday Hart, right? I auditioned for that role. It's you. What was the line? So you are. See, you are the bitches. It was because of you bitches that this bitch has been ignoring me for months. I remember. That was part of the line, right? It was a dress. All right, whoever wants to say dress, go say something to Ving Rhames about wearing a dress. You ain't gonna do it. And what people don't understand is like, this is a art, right? This is an art. Now. Now, I'm not saying it's for everybody. I'm not saying it's for me. I'm telling you, when it hit me, when I was like, man, who give a about what people say? I was doing an episode of Wilding Out. Pull up to Tyler Perry Studios military base. You been there?

[Teddy D]

I haven't been there, but I know it is the program.

[Dave Chappelle]

Wait for you to go up in there. Military base. Eight lanes on each side of the studio. You drive through that shit, you make go down, make a right. Harry Belafonte Studios, Oprah Winfrey Studios, Sidney Poitier Studios, and I looked back, I was like, from a dress. From a dress, right? I was like, I'm a size 8. But it's people, they have too much time on their hand to make the argument. And I guarantee you, Shani, any the most people that talk that shit about, blah, blah, blah, blah, blah, look at what they doing in life. It's probably a nigga to borrow his girl car. Bring it back on, E. Blunt guts all over it. You know what I'm saying? You just. It don't make no sense at any intelligent person will understand that it's all bullshit.

[Teddy D]

Right?

[Dave Chappelle]

You know, you don't want to get caught. And I know that. Oh, yeah, he look like he'll wear a dress. It ain't my thing. But I am not knocking somebody or judging them. Somebody that does that. And especially in comedy. Now, if I pick you up, we going to the club and you come out with a sequence dress, I'm like, yo, son, you gotta change that or at least change your heels or something. What up, son? Put some timbs on with that dress, nigga, you ain't gonna be going out here with us with that dress and them heels, the red bottoms.

[Teddy D]

But is that mainly in our community? Because you see Dustin Hoffman, you see. And Robbie Williams play that Miss Doubtfire. And I think Dustin Hoffman was in Tootsie. And you see so many other actors white.

[Dave Chappelle]

It is definitely linked to our culture because black culture is the most homophobic culture out there.

[Teddy D]

Right?

[Dave Chappelle]

You know what I'm saying? Certain. Like, they just. It just. It's what it is. It's the way I have a gay brother, right? And I was. I asked my brother, I said, do you think I'm homophobic? And he said, no, I don't think you're homophobic, but I do think you're homo ignorant. And the reason why I was. I was like, you know, I am ignorant. I'm not to say that I'm a bad person. The reason why I'm homo ignorant, because I was raised by homophobic people, of course. So how do I not be homophobic?

[Teddy D]

Correct.

[Dave Chappelle]

I was raised with uncles that thought anything could make you gay. Don't eat cottage cheese, nigga. Nah, they getting you used to consistency. I'm telling you, that's the gateway. You'll be like, walk, walk, walk. After that don't word pink. That's what I grew up with. But I do think that our mindsets have evolved to a point where the things I noticed that even in Kanye. Shame. It was certain things that I could say 30 years ago, it would get a laugh from the audience, right? Like, easy laugh, go ahead, you little. Whatever, you get a laugh that doesn't exist no more.

[Teddy D]

That's right.

[Dave Chappelle]

And I understand that the mindset of people in general have changed. My brother is. My brother with. My father had multiple kids. And I remember when my brother kind of came out, because when I was growing up, I just thought my brother had all the bitches.

[Teddy D]

Right?

[Dave Chappelle]

Right. I didn't know he was like, in that life or that's. I didn't. Because I was so young. I didn't really connect with sexuality. And I was too busy trying to build bikes and shit like that. So some time that went past, we had separated each other as a young adult. I was at a comedy club in Hollywood, and he came to the show and he said, we was outside, I was taking pictures. I was caught up in my moment. And I said. He said, you see that guy over there? I said, yeah. He said, that's your brother in law. When my father has so many kids, I thought he was introducing me to another brother. I'm like, man, I ain't got time for no more brothers, no more sisters. It didn't hit me till later on. I went home, I said, oh, shit. I think my brother just told me he was gay.

[Teddy D]

Right.

[Dave Chappelle]

I called my father. My father, I'm talking about a straight street dude, heroin kingspin in DC Whatever. Like Pu Ha guys. Straight, straight. And I said, dad, I think Chucky just told me he was gay. And my father said, man, I knew what he was up to. Like, being gay was up to something. Like, yeah, yeah, y'all caught you behind the bushes, right? He said, I knew what he's up to. And this is when I. When I said the way people think and their mind is evolved. And for my father to make this statement right here, it means a lot to a person's character. He said, I knew what he was up to, but he said, he was speaking on my brother's boyfriend. He said, man, but that's a good nigga, right? Right in that moment. And I knew that my father cared more about the character and the guy that my brother chose to be in love with than what anybody else can think. And I do believe, and I do think that mindsets have changed so much when it comes to that. Right.

[Teddy D]

Let me ask you this. The Chappelle show, how did that come about?

[Dave Chappelle]

The Chappelle show came about.

[Teddy D]

Were you friends with Chappelle before the show?

[Dave Chappelle]

Did you know? Yeah, I knew him, but we knew of Each other. Like going back to your question about the DC thing. Yeah, it's one thing about being a comic from dc, you always looked at the people that were before you and what moves they made. The first thing when you come from dc, the first sign that you really going for it, when you moved, right.

[Teddy D]

You gotta leave dc.

[Dave Chappelle]

You gotta leave. It's not like now you'd be on the Internet. You could be anywhere, right. You had to go to New York or la. So. And when I came out the gates, Shannon, when I tell you, first time I ever touched a microphone, I got to stand in ovation. Wow. I was doing comedy for five months and I made Def Comedy Jam. I was on fire. And Dave, this is on record, Dave telling this story. Somebody asked Dave at my 50th birthday, they asked Dave, where did you. Chris Spencer asked Dave. He said, where'd you meet Donnell? He said, I'm gonna tell you where I first met Donnell. He said, when I used to be in dc, he said I was the guy. And I would leave, I would be in New York, I would come home, and I would always ask, who's the up and coming? Who's smoking? And Dave said, it was always the regular names. Fat Dr. Andy, but the owner, Barbara, RIP, rest of the soul, she said, dave, but there's this one guy named Donnell Rawlins that's on fire. And Dave, the competitive nature he is, he said, that nigga. And then when somebody asked me, when I asked that same question, I said, who was popping? Who was. Who's got his smoker? They was like, dave. I was like, so what's so nice about him? He's like, he's smart, you know, he's animated. He's a good actor. They said all this shit. And I was like, I felt the same thing. I was like, man, fuck him. It was like a healthy competition. So we knew of each other. But my connection with Chappelle's show, it was Neil Brennan. Neil Brennan was a producer or an assistant for In Living Color when they were going out scouting talent. And he had me on a couple of audition tapes. And Neil Brennan and Dave had already wrote Half Baked, right? But the thing was, when they did that, Neil was popping as a writer. I think he sold two or three scripts to Hollywood. But his work wasn't being produced. It wasn't getting green lit. He was getting the money, but he wasn't getting green light. So he wanted to direct. He called my manager and said, I really like Donnell. I did this short, short film. I would like for him to be in it. Okay, it's just me, a Cameron, me and one other person, whatever. And he said I want him to do it. He said I don't have no money to pay him, but I like for him to do it. But this was the time I was on. I was on already started. The wire was on the corner. I was like, I know you can't afford to pay me, but if you're ever in a situation where you could throw me a bone, I'd appreciate it, right? But I'll do it. I did it. It maybe two months later. He said, I'm working on something. Neil Bren said, I'm working on something. I'm gonna let you know. I was like, I'm busy, whatever, right? I was like, what's the show name of the show? He said, we don't have a name for it. A month after that, Neil called me and said, I want you to be on the show. And that show. A lot of people don't toss back that show that he promised if he ever was in a position to look out for me. It was a chappelle show and of course I could have couldn't have been on the show without out the approval of Dave. But Dave, Dave was wanted to work with people that he just thought were funny.

[Teddy D]

Right.

[Dave Chappelle]

He didn't really know me as an actor. It was just like these are the guys. But Neil Brennan was definitely instrumental on my connection with that show.

[Donnell Rawlings]

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[Dave Chappelle]

Amazon One Medical presents painful thoughts. I could catch anything sitting in this doctor's waiting room. Okay, just wiped his runny nose on my jacket and the guy next to me sitting in a pool of perspiration insists on sharing my armrest. Next time, make an appointment with an.

[Teddy D]

Amazon One Method medical provider.

[Dave Chappelle]

There's no waiting and no sweaty guy. Amazon won. Medical healthcare just got less painful.

[Teddy D]

I try to tell people this, that the one thing that I know about in this business now, the entertainment side of it, and when you have advertising and sponsors, it's all about relationships. Yeah, if you do not have relationships, you're not gonna go very far in this business. It's really that simple. Because a lot of times the people that are in position now weren't in those positions years ago and they were smart and they remember how people treated them when they couldn't help them.

[Dave Chappelle]

Let me tell you something, I'm nice to 33 old. 33, 35. The reason why I say that he was 12. They was 12 when I was. I told my agents, yo, let's go for these 33 year old executives. They were 12 watching the show. A lot of the work that I get now is like this, man. I used to watch the show with me and my dad and you know, you start in relationships early on. I'm like these guys and I feel, and you know, I get this a lot of times, oh, he's riding Dave coattails, Dave's flunky, all of this shit, right? Oh, if it wasn't for Dave, guess what Dave had. His production company is called Pilot Boy Production. The reason why it's called Pilot Boy Production, because Dave had like 11 or 12 pilots before Chappelle's show. They always gunned for him, he was always getting shot. But for some reason, if it wasn't the right chemistry, the right team, it wasn't happening. It was the Chappelle show that came together and that was the one. So as much as you want to say as much as want to say it wasn't for Dave, guess what? If it wasn't for the team that Dave built, he wouldn't have won a championship. You give Jordan all the credit. He's the star. He needed rebounds. He needed somebody to push that ball.

[Teddy D]

Out, somebody to play.

[Dave Chappelle]

He needs somebody to say it. So as much as people want to say that, yes, that show was a platform for me, but I brought it. There's not a scene on that show that I didn't pop. If you listen to some of the most iconic phrases on that show came out of my mouth. It was their writing. But as much. And I'm forever grateful for what they did to me. But I know that I wasn't a bum, right? I put in work.

[Teddy D]

You carried your weight.

[Dave Chappelle]

And I always tell people, if you look at. I say my career is. If you want to compare it to anything. And I go to hip hop artists, Busta Rhymes. You might not remember too many of Busta Rhymes albums, but you know, when he came on the track, he was up and he was gonna bounce, right? And that was my relationship with that show.

[Teddy D]

You know what? That's what I hate when they say, oh, you know, you riding his coattails. Or if it wasn't for him. But the question is, if I'm not successful, what would you have said? I ain't got no talent. You know what I'm saying? You didn't say you rode Dave's coattail. It was all because of Dave. Now, if the show is not a success, you're not a success. What are you gonna say then? You gonna say, you just say, have no talent. Now that it's successful, you gonna say it's because of somebody else. You don't wanna give me the credit.

[Dave Chappelle]

Once we get the power of not giving a. That is. Yo, you think about it. The most successful, you know, once they.

[Teddy D]

Get to a point they don't give.

[Dave Chappelle]

They don't give a.

[Teddy D]

They care. They care less.

[Dave Chappelle]

But when you got heart, which I do have, and then. And when you care about what people think, which I do have, I think about that. And then we. Cause of social media, you get to instantly tell how people feel about you. You slide in comments, you get about it. But once you get to that point where you don't give a, that's when your shit start to pop.

[Teddy D]

But. And then when you don't care, you see how he turned his back on the people to help them get to where he got to.

[Dave Chappelle]

That's why I have the thing the notion. The notion. I do that. Like, you know what? Once I get to play, that's it. Yeah.

[Teddy D]

So when you started Chappelle show, could you have envisioned that it was gonna be what it became?

[Dave Chappelle]

Now I know I'm gonna piggyback on what you said about earlier, the Wire. I didn't know. Yeah, Chappelle's Show, I knew. And the reason why I knew Chappelle's show, because I was the warm up comic on that show.

[Teddy D]

Okay.

[Dave Chappelle]

Like when I say warm up comic, like when we did the wraparounds in the studio, I was the first person you ever saw on that show. It was my job to go out there and get the audience blow.

[Teddy D]

Yep.

[Dave Chappelle]

So I knew I could feel the energy from that audience. I knew it was gonna blow. And another thing, I used to call Neil every, every, every time episode. Cause I used to be like, I was in the streets. I was still in the streets, still in Brownsville, Brooklyn. And I was like, I would call them, I'm like, yo, I was talking to the Streets today. And they'd be like, what the Streets say? I said, the Streets say. That shit was funny as shit, right? Because, you know, Dave has had a level of success for the most part. Dave, earlier in his career, Dave been a prodigy. He's been a prodigy. And then he had a level of success way before a lot of us. And we say that all we wanted to do when we first started was to work in college circuit and make money. He was the king of that. They loved him. Main street loved him and everything. But for some reason at that point, his stuff was not resonating with the streets like that, right? He was like, why you give a about the Streets? Whoopi Goldberg, Mel Brooks, all these people, okay. But I just felt a certain energy when I go to the Barbershop when I used to talk to like some real street. And they was fascinated with that, right? Neil. And Dave was like, what did the Streets say? Because they know what the executives say, what the streets say. And every week I would. Every week I would just predict what the rating was going to be. It was over. It kept going bigger and bigger. And even like another reason on that show, if you're a historian, that shows show. You notice every time I did a character when I come on, people just went crazy. The reason why they went crazy because I was the warm up comedian before the sketch. So they would be connected to this stand up comedian. And then, oh, shit. So it was a bigger laugh. That's why when Beautiful came on that's why when Ashley Larry came on People, it came off a bigger laugh. Because they laughing at somebody that made them laugh before they even saw him in the sketch.

[Teddy D]

How did you come up with the character Ashley Larry?

[Dave Chappelle]

I didn't. Well, the character on paper, he was just a guy that had boxers on and dress shoes and stole his girl's money. But I knew on that show that I didn't get a lot of time to talk. So I knew that any character I had, I had to physically be funny before I even say anything. Cause I'm not gonna. If you had an editor on a timeline, how much time I talked on that show, I didn't talk a lot, right? But I knew that I wanted to be funny on site. So I went to Danielle. He was a makeup guy. I told him, I said, give me some baby powder, right? I said, I wanna be so. I wanna be so ashy. I could write how much money people owe me on the side of my leg. I wanted to be. I wanted to be the ashiest dude that when you see me go back and get the trash bag. That was real trash. I was like, how can I get the most? How do I get the most out of this? With the least amount of time. In fact, when we did World Series of Dice, that was the first time we had somebody outside of what was becoming the cast. Charlie Dave, Eddie Griffith Griffin was in that sketch. That sketch wasn't supposed. I wasn't supposed to pop that sketch. It was for grits and gravy. That was for them. But I just couldn't stop. I just. It was just something. I was possessed with something. I remember Charlie looked at me, he said, do you know what you're doing to this shit? I was like, I don't know. He said, man, you killing this shit. And I just went crazy. Cause I knew I might not be here next week, right? Eddie Griffin even said something to me. He said, donnie, you know what I like about you in this show? And in particular, he said, you're not afraid to get ugly. I want to say I'm not too far from it. You know what I'm saying? I ain't never called. Nobody ever called me Fine. You know, I was like. But he was like, just that person to get dirty. Don't give a. About what nobody think. And then I knew that I was just. I was just only. I was just fighting to be on another thing. But that's how the character was there. But I put the hot sauce on it, right? Yeah.

[Teddy D]

The success is having the show is having success beyond. I mean, you thought it was gonna be successful, but it probably, at this point, is even surprising you with the level of success that it's enjoying.

[Dave Chappelle]

Yeah.

[Teddy D]

And then you find out that Dave is gonna step away.

[Dave Chappelle]

Right.

[Teddy D]

Did he talk to you? Did he talk to anyone about that or just.

[Dave Chappelle]

It just broke out. But I felt we gotta realize that was going to the third season. Me and Charlie, we so excited. We got the Rich Bitch tour going on. We going back to the third season. You know, it's a chance there might be a situation where we can make more money, but we just excited about it. But I knew it was something weird because the last sketch I saw it was this show where we played monsters. I played a mummy, he played a wolf, and Charlie played Frankenstein. Whatever, right? And me and Charlie just having fun on set. We kicking that. We kicking it. And I saw Dave, he was a werewolf. And he was just looking like in the. And he said, I guess 50 million is not enough. And I would look at him like, who you talking to? 50 million not enough. I take the zero. You could take three more than zeros off. I'm good with it. And I didn't know that what was troubling. But that was just so. For somebody that still me still coming up, not used to having no big money or anything. I was like, I don't even understand how anybody can say, I guess 50 million is not enough. I didn't understand that. And then he disappeared. Not communicate with me. But you got to also realize when we was doing the show, me and they weren't the best of buddies. I tried to keep my relationship, be coworkers. I don't want to be all like.

[Teddy D]

Hey, buddy, buddy, buddy, buddy.

[Dave Chappelle]

Just let me go do my job, do my thing, and then go keep moving. So we never even that time we hung out after the show. We really got connected after the show, after he came back. But, like, he disappeared. And it was so funny. Cause I told Neil, didn't know where he was. And I said, man, I bet you he probably went to Africa. And Neil was looking like, why would you say that? But I remember we were in the green room one day. It was me, Dave, Mos Def. And Dave was. I think Mos Def was a real estate agent in Africa because he was trying to get everybody to come to Africa. I wanted to say, yo, you can't get all of Brooklyn to come to Africa. Then Africa becomes Brooklyn. Make it a secret or whatever, right? But I just had this weird feeling that he probably went There. Then cut to maybe two, three days later that they announced that he was in Africa. But for us, I never thought. I didn't know what the severity of what his thoughts were. I never thought that he wasn't gonna come back. In fact, when he left, we was like this, all right, we can go back on tour now, right?

[Teddy D]

Because we had thinking he was gonna come back.

[Dave Chappelle]

Yeah, we was like this. Oh, man. Yeah, let him take three months off. I'm just thinking about the money we gonna stack up to come back. But he never came back, and he never communicated anything to me.

[Teddy D]

Do you believe there was a number that he would have been willing to come back from? Or he was just over being underpaid for such a long time that he's like, 50 million. If y'all gonna pay me 50 million. How much are you guys actually making?

[Dave Chappelle]

I don't know. That's a tough question that only Dave could probably. They could answer. But at the same time, I know he loves money, but he's not driven by money. You know what I'm saying? I think that it was probably. It probably more than likely something morally he didn't agree with.

[Teddy D]

Right.

[Dave Chappelle]

But I don't think it was. I don't think that his decision to walk away was just the money. But I think that when he came back, it's like, now give me my money.

[Teddy D]

Right?

[Dave Chappelle]

Yeah, but I don't think that that was that.

[Teddy D]

When you did the blacks get reparation skits, you know, Prince. You know, the skits are classic. The Rick James, the Prince. Did you. I mean, when you're, like, on set and you seeing him doing these skits, Because I can just imagine. To hold it together.

[Dave Chappelle]

Yeah.

[Teddy D]

Did you ever, like.

[Dave Chappelle]

We never held a hell together. We never held together before. We blew so many takes. It was so many takes that we were always thought about what we had on paper. Right. But then he's so genius with sketching. It was always like, yeah, that's what's on there. But he always had something in his back pocket. He always had a draw for that. He was going to throw something. And then after a while, he kind of trusted us to get kind of loose and add that element to it. But it was. I guarantee you half the stuff that was written on that paper never made it. And we just got loose with it.

[Teddy D]

Is that what makes you. Is that what makes him so good, is that he's a. And most comedians have this ability. Is that their ability to improv? Yes. It's on the. It's on There. But if you let me do it my way, Cat said that. Let me do it my way and I promise you it'll be ten times funnier.

[Dave Chappelle]

But you can't always. But see, that's the problem, that everybody's not gonna agree to that.

[Teddy D]

Right.

[Dave Chappelle]

And the reason why, that you got writers that are getting paid a lot of money. You know, it's kind of insulting if you just, just basically saying, I'm gonna do all of that. Some people, they did. That's the only way they can work.

[Teddy D]

Right.

[Dave Chappelle]

But even in our case, we never want to disrespect the writers. We would do with Brian Tucker nailed and put on paper. Then it was like this, okay, let me get one. You know what I'm saying? But no, you're not going to have too many sets that's going to let you do whatever you want. Yeah. Because then now you start doing that. Now they got to pay you as a writer. There's a whole. A bunch of things. But it wasn't. But what the thing that, what the thing about working with him is that he makes you go harder. It makes you want to be the best that you can be.

[Teddy D]

Is it true that R. Kelly sent Goons at Chappelle?

[Dave Chappelle]

I don't know. I don't know if it's true that R. Kelly sent Goons, but I know we had goons too. So it was gonna be a goon interact, it was gonna be a goon encounter. Yeah, it was gonna be a goon convention, but I don't know too much about that, but damn, man. That was another thing we was like, like it was, it was. The show was fearless. It's like we gonna say what we want and not care about what you think, but we do the funny first and deal with it after that.

[Teddy D]

Could there be a Chappelle show today?

[Dave Chappelle]

That would be a tough one. That would be a tough. I think certain things. I don't know if there could be a Chappelle show, but it would be interesting if there was a one off, you know?

[Teddy D]

Yeah.

[Dave Chappelle]

Just. But it's just so hard because now you gotta.

[Teddy D]

Today's society is a lot different than today.

[Dave Chappelle]

But it's about to change though, Shannon. It's like, I think it is. I think that. I think that the idea of Cancel culture is about to be dead good. People getting frustrated with that. And after a while we went through that stage. You can't say this, can't say that, but people are getting sick of that. If anybody could, if anybody would be able to Pull it off, it would be him. But I think that it's going to be time for us to get back to like, not concerning ourself with what you think and what we think is funny and put it out there.

[Teddy D]

If I'm not mistaken, I think I read that you. What's the 11 color? Yeah, which is kind of, I mean, Chappelle before Chappelle.

[Dave Chappelle]

Yeah. What about the 11 color?

[Teddy D]

Didn't you audition for that?

[Dave Chappelle]

I auditioned to it. I auditioned for it, but I was green. I didn't know what I was doing.

[Teddy D]

Okay.

[Dave Chappelle]

I auditioned for that. I was like I said when I first started, I came out hot, but I just, I was green.

[Teddy D]

Right.

[Dave Chappelle]

I was funny as a stand up. And I had a couple of little quirky little characters and things I was doing that was different from everybody else.

[Teddy D]

Right.

[Dave Chappelle]

But I wasn't ready for In Living Color. I auditioned for Saturday Night Live. That's where I met Neil. And in fact, that audition, I did a Saturday Night Live. Tracy Morgan was on that same audition and he got it. I was a guy that told a funny story but did not understand. When they say we need three original characters, what that looked like. I was telling long stories. And I remember Tracy Morgan, he did a character, a black hockey player. And it was a very simple character, but he really committed to the character. Like he had the little things on everything. And I saw he looked like a sketch, but I wasn't ready for that. Yeah, but you.

[Teddy D]

So you didn't understand. You understand now. Now you probably go on an audition, you understand, they send you the format, what they're looking for. You go in there, you know what they're looking for, you become that.

[Dave Chappelle]

Yeah, but back then I was only getting shots because I was funny as a standup, right. But again, I wasn't trained. I didn't know what I was doing. And there was, you know, when I looked back, I was like, oh, if I was prepared for that, I probably could have got it right. But it wasn't. I've been. I always say it's a tortoise in the hare. I've been a tortoise for so long, I don't have a problem with the slow route, how it's going. As long as I get my money now and keep going, I'm good.

[Teddy D]

Comedy Central moves in a different direction. They do Key and Peele, which does a lot of what you guys were doing, right? Did you feel any sort of resentment where you like, bro, y'all, that's us. All they did is Key And Peele. But you guys are doing what, me, Chappelle, and Charlie Murphy. Perfect with you.

[Dave Chappelle]

No, I don't. I don't. I don't. I don't believe that. The reason why everything has a moment in time. Okay, you're gonna compare it first off, to try to replace that time slot and everything. Of course you're gonna compare it, but there's no way. I just. A lot of the Key and Peele stuff have been coming up on my timeline lately, and I was like, they were some funny. They were some funny. And it could have been reversed. It could have been. They could have came before Chappelle's show and it would have been reversed. I think it was a timing thing. I think that they was in one of the toughest spots you could be to come behind a show that became so much part of pop culture. And then you all. I know everywhere they went, they was like, oh, y'all trying to be Chappelle Show. It's sketch comedy.

[Teddy D]

Right.

[Dave Chappelle]

You know what I'm saying? And then there's something to be said for, like, basically there was two actors that read all these things, you know, in the moment. People like, same time slot, whatever. But.

[Teddy D]

Right.

[Dave Chappelle]

I don't think. I don't. You know, but it had to be.

[Teddy D]

Good because it stayed for an extended period of time. So they.

[Dave Chappelle]

They had to be good. They could have just trying to prove a point to Dave. Like, we got another nigger. We're good. You know how those people upstairs are. No, just joking.

[Teddy D]

Let me ask you this.

[Dave Chappelle]

Yeah.

[Teddy D]

Let's just say, for the sake of argument, Chappelle's show is going. And we got the thing going on with Diddy. Would y'all have poked fun of that?

[Dave Chappelle]

I'm pretty sure we poked fun of Diddy before. Diddy was Diddy in.

[Teddy D]

Poke fun of the man before.

[Dave Chappelle]

If you notice, Dave played Diddy and he had a lot of baby on his leg. He had Dave over. Dave knew something that we didn't know. Dave knew something that oil was gonna come in. Dave had one bottle of baby oil in that scene. Take that, take that, take that. Of course he would have. Cause we would have made fun of the things that's happening right now that have been a tough one.

[Teddy D]

Hold on. I'm trying to figure out. Hold on this.

[Dave Chappelle]

But who haven't trafficked Shannon?

[Teddy D]

A lot of people.

[Dave Chappelle]

You ain't never trafficked nobody.

[Teddy D]

They have not.

[Dave Chappelle]

I know you gonna say the right thing right now. Ooh.

[Teddy D]

Ain't no right.

[Dave Chappelle]

I know you gonna Say, ain't no.

[Teddy D]

Right thing right now, tomorrow, yesterday. No. Ain't no traffic going on. No. Hold on.

[Dave Chappelle]

Can I ask you a question?

[Teddy D]

Yeah.

[Dave Chappelle]

Okay. You.

[Teddy D]

Yeah.

[Dave Chappelle]

Successful athlete.

[Teddy D]

Yeah.

[Dave Chappelle]

A lot of money.

[Teddy D]

A little bit of money. Not a lot.

[Dave Chappelle]

Don't try to downplay it.

[Teddy D]

I got a little bit bunny hopping.

[Dave Chappelle]

I'm just saying. I'm just saying, not one time I.

[Teddy D]

Beat you to the sister.

[Dave Chappelle]

In your successful life, you have not flown someone in with the intentions of having sexual intercourse with him.

[Teddy D]

My girlfriend.

[Dave Chappelle]

You should be a lawyer. God damn, you smart. I believe it to death. I believe her to death. I'ma leave it at that.

[Teddy D]

Hold on. Is this true you got about you sitting between Diddy and Russell Smith?

[Dave Chappelle]

Nah, See, first off, first off. First off. First off.

[Teddy D]

Okay, get to the second part.

[Dave Chappelle]

Okay, second part. First off. All right, What I'm trying to tell you is. All right, that what I'm. Okay, let me explain something to you. Yeah, no, no, hold on.

[Teddy D]

Let me take a look.

[Dave Chappelle]

Nah, I take a shot. I'm gonna tell you. I'm gonna tell you. I'll tell you. It's a photo that's going viral. That 10 years ago, Shannon would have been a photo that would have been iconic and people would have wished they was in that picture. It wasn't until after the freak off shit, that now picture looks suspect. But you look at that picture, Shannon, you see it different from me. What I saw in that picture, first off, I saw eight successful black men, okay? I saw. And I was there talking about friendship, creating general. Why you. General sitting between your legs. Can I finish? Goddamn. See what I'm saying?

[Teddy D]

Let me. Can I get another drink? Because I want to hear this story.

[Dave Chappelle]

It's just my truth, which is I saw black excellence in that picture.

[Teddy D]

That's what you saw.

[Dave Chappelle]

All right, first off, all right, this.

[Teddy D]

How it happened, okay?

[Dave Chappelle]

This how it happened. They was hating on me. I was on that boat, that yacht, and I was up, right? I was really.

[Teddy D]

You remember what happened, don't you?

[Dave Chappelle]

Trying to suck me up. Nah, don't do that, don't do that, don't do that, don't do that, don't do that.

[Teddy D]

You say you were best off.

[Dave Chappelle]

I know, I know. Don't talk about that memory shit, all right? I don't mind where that. I knew exactly what happened, which was nothing. But I was lit. I knew I was lit. You know, I knew I was fucked up. Cause Diddy looked at me like, damn, somebody get this off the boat. I was lit. And so they was really, just everybody was mad. I was having a good time. And they was trying to take this picture, right? And everybody was taller than me. They was trying to block me out. They was already frustrated with me, right? So I did. And it was a situation like this. I swooped around, went into the front of the picture, and I did like this. I did not know this nigga was right here behind me. And I. You know what? Why you asking me to tell you my story and you don't want to hear my motherfucking story? Or you could have just said. No matter what you said, watch. He was in between his legs. And I wasn't imagining. It was the depth camera, people. It was the depth of the photo. What do y'all call that shit when it's not focusing, it's blurry. It was that.

[Teddy D]

It wasn't blurry enough. We couldn't see you.

[Dave Chappelle]

Yo, I didn't know. I didn't. Listen, man. I had a good time in that boat, all right? Yeah, I left. I left.

[Teddy D]

Most people that was at these situations, it ain't.

[Dave Chappelle]

It's the difference. Oh, that was a family. It was family. My son was on that goddamn boat.

[Teddy D]

I used to hear him in the picture.

[Dave Chappelle]

I'm just saying, I be. See this, what we talking black on black crime right here. And this is why I love that you in my standing routine now. I'mma get you back. I got you. Oh, I. I'm sending you some videos. I was waiting for this. Let's go. It's too late. Don't cop and plea now. It's already popping. Come on, Cat. No, no, Cat, come on, come on. I got a whole 20 minutes.

[Teddy D]

But I'm just saying. But look, in all seriousness, you have defended.

[Dave Chappelle]

I did defend. I defended. Who?

[Teddy D]

The parties that you didn't know.

[Dave Chappelle]

What? First off, it's different parties, all right? You can't. I didn't defend no party. I defended what that was all right. And that was family oriented.

[Teddy D]

But you don't remember a whole lot that day.

[Dave Chappelle]

You know what? Let me get a drink. Cause I'm not gonna let you do this. I'm not gonna let you do this. I am not defending. What I'm saying is, of course there have been freak offs. And of course, how you know. I read the same blogs you read. I read the same. How I know. God damn, this nigga turned to a lawyer. No, I'm saying. Okay. Word is on the streets. Okay? Right. Everybody know it's freak offs. Everybody know Hollywood is Hollywood. I don't understand why all these motherfuckers act like, oh, my God, they had a mansion party and they had cocaine and all these orgy drugs. And why the people don't know? I'm not saying you gotta be a part of it, but why is this whole thing? It's like, I can't believe they were doing that in Hollywood. And I understand Cat Williams came up here, and it's part of my routine. I said, cat Williams on this couch for three hours, and his feet never touched the ground. That's the first thing I said, right? Y'all didn't see the same thing I saw.

[Teddy D]

Y'all didn't see that, you know, Cat coming back.

[Dave Chappelle]

I don't give a. Why they give a. Am I scared of Cat Williams? No. For what? He probably come back, start your year off right. But I noticed feet was like this the whole time. And I told him, and I don't disrespect him, whatever, but part of my routine, I said cat wasn't a funny person everybody think was funny. You was the funniest. Because it didn't matter what the Cat Williams said. You said, oh, come on, Cat. You can't say that. I thought he just said it. Give me a card. Give me a card. You was like this. Oh, come on, Cat. No, Cat, come. Oh, Cat. Come on now, Cat. Oh, there you go. There you go. Oh, Cat. These my friends, Cat now. Come on, Cat. Cat, Cat, Cat, Cat, Cat, Cat, Cat, Cat, Cat. Oo, oo, Ocho, Ocho. Hey, Skip. Skip, Ocho. See, the difference between me and you is you wear your watch to tail tie, all right? And I wasn't every party Diddy had, and I wasn't at too many. Okay, wait, I was at. How you helping? You the cameraman, man. What you doing? No, I'm just saying I don't know that side of it. That's what I'm saying. And I'm not defending anything. What? I'm defending what that incident was. He does a party every Christmas holiday. Saint Martin. Saint Bart. Saint Martin. Saint Bart's Whatever it is. And it was a gift exchange. Huh?

[Teddy D]

A gift exchange.

[Dave Chappelle]

We had dinner, okay? No gifts were changed. It was just a vibe. I was there. We was vacationing with Dave. It was a survive. We went over there. It was a vibe. And the thing. I'm gonna tell you, the thing that I did like about it, that party, was that Kimora was there. Yeah. Kim Porter was there. My baby mother was there. Dave's kids was there. And I was one of the only thing I saw And I don't know what happened to anything else. What I saw was a vibe, okay? What I saw was a good thing. And that's what I'm saying. Anytime you say anything about. Oh, you're defending. I'm not defending. I don't know nothing about the free parties. But I do know right? Damn, nah. Cause you about to get crazy. No, I can tell. I gotta get loose for this. What? I go ahead and say it. That's how diddy parties start, right? No, I'm just saying. Let me put my towel back on. I know you about to say some slick shit. I know. Yeah, that's how it gets. You take the towel, start throwing your shit around. I'm not saying that. What I'm saying was. What I know was that was family joint and was cool. People can make out what they try to make it to see what it was. That's not what it was for me. That's what I was.

[Teddy D]

Okay. I'm not here. You know, I cast no judgment. I don't look at you with judgy eyes. That's your story.

[Dave Chappelle]

If you could do a close up. Those are very judgy eyes right there. Yo, your eyes judgy as shit. Anytime you take your glasses off and wipe your shit off, them judgy eyes, man.

[Teddy D]

Cause I've been crying, man. You had me up here crying.

[Dave Chappelle]

No, I'm just saying it is what it is. I know. I. I said no, Diddy.

[Teddy D]

Yeah.

[Dave Chappelle]

I said it. So you know he coming home, right?

[Teddy D]

I don't know, man. I don't. Look, honestly, I don't pay attention to that stuff.

[Dave Chappelle]

I know you don't.

[Teddy D]

I don't cause it. I'm sorry for the people that was impacted by it, but that ain't got nothing to do with me, man. I ain't never been to nobody's house.

[Dave Chappelle]

Why the fuck you ask me?

[Teddy D]

Cause you the picture.

[Dave Chappelle]

No, you could have just. If you really.

[Teddy D]

I mean, they say you was in the picture like that.

[Dave Chappelle]

I wasn't like that, son. I wasn't like that. I was in it like that. I was like. I was like the most interested man in the world said I was like this. I was doing real shit. Who wanna drink? That's what I did.

[Teddy D]

But it was the fact that you between the man legs, though, that the nigga legs.

[Dave Chappelle]

I wasn't in between his. He was right there. Yeah, I was right here.

[Teddy D]

But you lay it down like.

[Dave Chappelle]

I wasn't.

[Teddy D]

Like.

[Dave Chappelle]

I didn't even know he was back there.

[Teddy D]

How you not know he was back there. You snuck in the picture.

[Dave Chappelle]

Listen to what I just said. All these people right here. Yes. I can't see who in the front. Shannon.

[Teddy D]

Okay.

[Dave Chappelle]

I can't see who in the front, so I run around the side. I couldn't see. I didn't even know he's here.

[Teddy D]

I turned around. It just so happens you photobombed and you between the man's legs.

[Dave Chappelle]

That's. You know what? I photobombed and I was in an awkward position. You don't gotta say between somebody's legs. That's what I'm saying. You got the wrong word. Place. I photobombed and was in a situation where people perceive to be very suspect. Okay. Or as the kids say, sus. That's what it was. You could take.

[Teddy D]

How would you perceive it? If you look. If you're not. If you're not the person, that's. How would you perceive it?

[Dave Chappelle]

I was looking if I saw that picture.

[Teddy D]

Yeah.

[Dave Chappelle]

I would say, you know what? It looks like Black excellence is in this photo. Right. And these guys was having a good time and it slipped into a compromise position. That's what I did, son. No further questions.

[Teddy D]

This concludes the first half of my conversation. Part two is also posted and you can access it to whichever podcast platform you just listened to part one on. Just simply go back to Club Shay Shay profile and I'll see you there.

[Dave Chappelle]

I'm Peter Schrager, host of Good Morning Football on the NFL Network and the Season with Peter Schrager podcast. Whether you're ordering wings for the game or you're whipping up a seven layer dip, or you're ordering a pizza, there's something about football that makes you want to eat in this football season. UberEats has the best deals on game day food. No matter what you're craving. From two for one pizzas to buy one, get one wings to whatever it is you want. UberEats will be dropping new deals each week all season long. UberEats is the official on demand delivery partner of the NFL. Order now for game day. Terms and conditions apply and see the app for details.

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[Donnell Rawlings]

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[Dave Chappelle]

Check.

[Donnell Rawlings]

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