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Why Comedian Dave Chappelle Walked Away From $50 million | The Oprah Winfrey Show | OWN

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- So what happened to Dave Chappelle? He's here today to talk about it in his first television interview. Please welcome Dave Chappelle. [APPLAUSE] [MUSIC PLAYING] How you doing? Fine. Fine, fine, fine. I'm glad you're here. Everybody wants to know, why'd you walk away from $50 million? Well, I wasn't walking away from the money. OPRAH WINFREY: Yeah. [LAUGHTER] I was walking away from the circumstances-- OPRAH WINFREY: Uh-huh. --that were coming with the newfound plateau. OPRAH WINFREY: Yeah. It takes a while, when you punch through a-- to adjust to the atmosphere. It was completely outside of my frame of reference. I've been in show business since I was 14. And I've heard the stories of what happens. And I've seen these kinds of things play out in front of me-- - OK. --when I saw those things. When you heard the stories, what do you mean? What stories? I mean, you see before-- look, Mariah Carey made $100 million deal. And three months later, she's all of a sudden mysteriously crazy. Or Martin Lawrence punches through, and he's waving a gun on the street, screaming, they're trying to kill me. [LAUGHTER] OPRAH WINFREY: Yeah. Yeah, yeah, we hear those stories. And it always happens around the time when the career would have-- it seems as though they're crossing over the next plateau. OPRAH WINFREY: Yeah, yeah. Would you say you lost your mind, sort of? No. OPRAH WINFREY: No. Not exactly. OPRAH WINFREY: OK. I wasn't crazy. But it's incredibly stressful. OPRAH WINFREY: Yeah. DAVE CHAPPELLE: And I felt like, in a lot of instances, I was deliberately being put through stress. Because, you know, when you're a guy that generates money, people have a vested interest in controlling you. OPRAH WINFREY: Yeah. Were they trying to control you? Because, you know, I read the "Time Magazine" article. And they were quoted as saying, you had extreme creative control, and that you really ran your own show. Yeah, OK, but Oprah, I did two very successful seasons before that. So why, all of a sudden, on the third time, am I in Africa by myself? Like, what's happening? Yeah. So what happened? Did you find yourself spiraling downward? Well, first of all, yeah. But I don't want to make it as a thing where I'm absolving myself of any responsibility of it. OPRAH WINFREY: Yeah. Obviously, I'm partially responsible. You know, a lot of it has to do with me. Was there a tipping point for you? DAVE CHAPPELLE: I'll give you an example. The first season ends. OPRAH WINFREY: Yeah. And in the middle of the seasons, there was a renegotiation. OPRAH WINFREY: OK. DAVE CHAPPELLE: Ultimately, through a series of events and a little pressure, I ended up settling for way less than what I wanted, and going forward. And then in season 2, the DVD is released, and it sets all these incredible records. Turns out, the back-- OPRAH WINFREY: Half a million in one day-- DAVE CHAPPELLE: Right. --$2.2 million in a week, the largest-selling television DVD of all time. DAVE CHAPPELLE: Yeah. Yeah. So now suddenly-- suddenly, this is a bigger money-maker than they thought. It was already making money. But now, all of a sudden, it's a whole new revenue stream. And my contract's up. Mm. [LAUGHTER] OPRAH WINFREY: Yeah. Yeah. DAVE CHAPPELLE: You know? So we finish the season. So now, you know, the show is gaining popularity. Ratings are up every week. It's-- I'm the toast of the town. OPRAH WINFREY: Yeah. And when the season starts ending, you know, you get the question. So, uh, Dave, uh, what are you gonna do and blah, blah, blah. And I knew to be real tight-lipped about it. You know, it wasn't like Comedy Central was a hot place to be when I showed up there. [LAUGHTER] Yeah. But you turned it around. Your show turned it around, became the most popular. That's what I was thinking. OPRAH WINFREY: Yeah. [LAUGHTER] Yeah, yeah. You know, so-- and then, this the thing. We're having argue-- all these arguments. Dave, you got cut the poop joke. [LAUGHTER] And there was a lot of discussions about, we know what our audience wants. I was like, ah, whatever. And I mean, they were wrong 100% of the time-- OPRAH WINFREY: Uh-huh. --as far as what people will like. OPRAH WINFREY: OK. DAVE CHAPPELLE: And the show is an incredibly hard show to do. That's the other thing. "Chappelle Show" was-- I mean, it's fun and all these things. But there's a tremendous amount of work that goes into making a show like that. Yeah. People were saying, though, that you were on drugs, you lost your mind, you went into a mental institution. What is true? What is not? Not on drugs. OPRAH WINFREY: Not on drugs. Nah, not for years. [LAUGHTER] OPRAH WINFREY: OK. - I'm just playing. No, I'm not on drugs. OPRAH WINFREY: And you weren't on drugs at the time. No, no, not at all, not at all. OPRAH WINFREY: No, OK. DAVE CHAPPELLE: I'm telling you, I was incredibly stressed out, you know? Love is like a nutrient. And I was deficient on vitamin love. OPRAH WINFREY: Really? [AUDIENCE SAYING "AW"] Were you really? [LAUGHTER] Ah. I'm on Oprah, baby. [LAUGHTER] Ah.

Now, really, what was going on? Man, where do you start? Damn this story. [LAUGHTER] I-- I was doing sketches that were funny, Now, really, what was going on? Man, where do you start? Damn this story. [LAUGHTER] I-- I was doing sketches that were funny, but socially irresponsible. OPRAH WINFREY: Mm. I felt like I was deliberately being encouraged, and I was overwhelmed. So it's like you're getting flooded with things, and you don't pay attention to things like your ethics or when you get so overwhelmed. It's like you had won the lottery. Explain. DAVE CHAPPELLE: Let's say for your handlers, for instance. Yeah. A lot of these people traditionally get paid on percentage basises. The more you work-- OPRAH WINFREY: The more they make. DAVE CHAPPELLE: --the more they make. Yeah. You make that real money, they lost their minds. I thought they were crazy. You know, it was like, you got to do everything. Yeah, yeah. DAVE CHAPPELLE: So I got all these things. Then I got, you know, your own personal problems that get inflamed when this kind of money comes in. And I got to write a show and do the show. And I was overwhelmed. And it was almost like-- I don't know. It was almost as if this was happening deliberately. OK. You mentioned a moment ago that you felt that there were some things that weren't socially responsible. Like what? Like, there's this one sketch that we did that was about this pixie that would appear whenever racist things happens, whenever someone make you feel like they calling you that N-word, but don't say it. And it was it was funny. And the premise of the sketch was that every race had this, like, pixie, this, like, racial complex. And-- but the pixie was in blackface. Now, blackface is a very difficult image. But the reason I had chosen blackface at the time was because this was gonna to be the visual personification of the N-word. Right. It was-- it was a good spirit or intention behind it. But what I didn't consider is how many people watch the show, and how-- the way people use television is subjective. I completely understand. DAVE CHAPPELLE: Yeah. I-- finish, because I have a story to tell you. So then when I'm on the set and we're finally taping the sketch, somebody on the set that was on white laughed in such a way-- I know the difference of people laughing with me and people laughing at me. And it was the first time I'd ever gotten a laugh that I was uncomfortable with. OPRAH WINFREY: Mm. Not just uncomfortable, but like, should I fire this person? [LAUGHTER] And at the same time, I'm just not a naturally assertive person. What was it about the laugh? I know all these people be watching TV, that there's a lot of people who understand exactly what I'm doing. Then there's another group of people who are just fans, like the people that-- the kind of people that scream "I'm Rick James," be at my concerts. OPRAH WINFREY: Yeah. They're just along for a different kind of celebrity worship ride. They're gonna get something-- Completely different. DAVE CHAPPELLE: Completely different. Yeah. DAVE CHAPPELLE: That concerned me. - Yeah. - I didn't want-- I got to-- I mean, I don't want black people to be disappointed in me for putting that out there. OPRAH WINFREY: No, you didn't want to be disappointed in yourself. You know what, Oprah? [LAUGHTER] You're right. OPRAH WINFREY: Yeah. I still haven't gotten to why you just disappeared. So you had that moment. The guys are laughing too much. Was that the tipping point for you? Was that the straw? That was the first tipping point. OPRAH WINFREY: OK. And then they put in the people that I had pneumonia or god knows what. OPRAH WINFREY: Mm-hmm. It was walking pneumonia, 'cause I was walking all over the place. [LAUGHTER] I was relaxing. And then after that, I was coming back to the show. And then they were like, well, Dave, you know, you should just back up the pneumonia story. And I was like, you know, that was your thing. I'm not-- I'm not backing up a pneumonia story. And then the next day, it was in the paper that I had writer's block. Then I knew something was getting ready to get stressful, because I hadn't even started writing. It wasn't-- I was on schedule to write. So I was like, what's-- you know, what's going on? Are they gonna-- OPRAH WINFREY: So these are your people trying to feed-- DAVE CHAPPELLE: Manipulate. It sounds like somebody's trying to put young Dave in a compromising position. [LAUGHTER] Mm-mm, Oprah. OPRAH WINFREY: Mm-mm, mm-mm. DAVE CHAPPELLE: But you know, OK, so now it got worse. And when I said I'm not gonna do it, then all of a sudden, it was like, well, now he has walking pneumonia. And then I knew long before I walked I had considered walking. OPRAH WINFREY: You had considered it. I had considered walking. Because I went back to work, and the vitamin love was gone, because it was a real ugly negotiation. It's a situation, where now, everybody's taking credit for this and that and the other. It's all-- it's just-- it was getting ridiculous. And I knew I was gonna leave.

So I got ahead of schedule, and I bounced. And I didn't tell anybody where I was going. The whole time, they're trying to convince me I'm insane. So I got ahead of schedule, and I bounced. And I didn't tell anybody where I was going. The whole time, they're trying to convince me I'm insane. They were trying to get me to take psychotic medication. Yeah, like I'm sitting around-- you know, I was stressed out. But the people that were telling me I was insane, I believe that they knew what was going on. So this was troublesome. [LAUGHTER] Yeah. DAVE CHAPPELLE: I said, I'm not taking this medicine, man. Because I know how these people be trying to control you or maybe discredit you. I was afraid, like, you know-- OPRAH WINFREY: But you were stressed out. That's why-- DAVE CHAPPELLE: There's no question. But it's very stressful for someone to constantly walk behind you and say you're insane. Oh, hey, how 'bout this? I show up to work the first week, and they-- where my office used to be, they built a wall there. [LAUGHTER] OPRAH WINFREY: Why? I didn't know why. But it came out later that they were like, well, they said you wanted it. I don't want to be walled up at the office. [LAUGHTER] I like hanging out and talking. OPRAH WINFREY: OK, so you got up and you walked out, and nobody knew where you were going. Did your family know? Nah. Well, no, I called my brother. OPRAH WINFREY: Yeah. Me and my brother are really cool. I called him up and was like, I'm going to Africa. He was like, cool man. That's good. Did your wife and children know where you were going? DAVE CHAPPELLE: No. - No. Nobody knew. No. I bounced. Now, that sounds a little crazy. It's not crazy, because the situation kind of warranted it. OPRAH WINFREY: OK. Because certain people around me were putting my sanity in question, I would meet too much obstruction if I would say I'm doing something like this. OPRAH WINFREY: Yeah, OK. So I figured-- it wasn't that I didn't tell my wife. It was like, I'm not telling her till after I'm gone, which was a mistake. But it wasn't a crazy mistake. It's just a dude's. [LAUGHTER] OPRAH WINFREY: Yeah. Yeah. DAVE CHAPPELLE: It's just like-- As a husband, she should have known where you were gone. Is that what you're saying? She was gonna know. You know, I basically-- I called my brother. I told-- and I gave him a list. You call so-and-so and so-and-so and so-and-so. And I took off. Then I called my wife. OK. Why were you going to Africa, specifically? One, I needed a break. OPRAH WINFREY: Needed a break. Two, we have family friends down there. And three, I just felt like it was a place where I could really reflect. Just a place that I got to go. And what did you conclude about yourself? Oh, well, that I wasn't paying attention. I felt really guilty about being asleep at the wheel. OPRAH WINFREY: Mm. I felt guilty about it, because I forgot the hostility of the environment of show business. It's-- you know, it's not a docile environment. It's a challenging environment. OPRAH WINFREY: Yes. You know? And there's some quote that someone had told me. It says, success takes you where character cannot sustain you. Wow, that's a good quote. Yeah, I don't care who you think you are or how you think you do it, you cannot imagine what celebrities go through, as far as how your integrity and your self image and all these things are challenged. OPRAH WINFREY: OK, this is a theory that I've always had, and I've discussed this with other people, the idea that if you don't know who you are when this big thing hits, when the big stuff comes, if you don't know who you are and can't stand in the center of yourself, then you end up confused and feeling thwarted and feeling diffused in many directions. Because everybody is pulling on you. Would you say that that was a part of your issue, trying to figure-- find the center for yourself? DAVE CHAPPELLE: Absolutely. When you are suddenly given a $50 million contract, when you've been making I-don't-know-what before, that is a lot to orchestrate, to handle, and a lot for other people to figure out. In that sense, it was like, all right, you're the CEO of a $50 million company. Good luck. [LAUGHTER] OPRAH WINFREY: Yeah, yeah. Now you figure it out. - Right. But you've worked your whole life for it. DAVE CHAPPELLE: Yeah. - You wanted it. You, you know, struggled to get it. Sacrificed. You sacrificed, rejected many times, told that things wouldn't work, wouldn't work, wouldn't work. And then all of a sudden, you're the genius, and we're gonna give you $50 million. And that was too much for you to handle? No. That's the thing that I always read that makes me mad. No. It was the fame. He couldn't stand the fame. OPRAH WINFREY: Yeah. I love being famous. OPRAH WINFREY: Yeah. [LAUGHTER] - It's phenomenal. When I came out here and everybody was like, hooray, I was like, ah, back on TV! [LAUGHTER] [APPLAUSE] OK, so that's clear. It's not the fame. It's what? It's the way that people around you position themselves around you to get in your pockets and in your mind. OPRAH WINFREY: Yeah, yeah, yeah. That, it's infuriating to me. You know, one of the phrases I always loved is, to whom much is given, much is expected. And part of it is-- I know, I'm like Spider-Man. Peter, with great power comes great responsibility. [LAUGHTER] OPRAH WINFREY: No, no, no, but it does. It does. And part of that is not just being up on stage. It's handling the rest of the business and handling all the people that are lined up at your door, for whatever reason. Yeah. Yeah, you're absolutely right. You just don't get the $50 million with no strings attached. DAVE CHAPPELLE: Yeah, but at a certain point it was like, all right, this is enough. OPRAH WINFREY: Yeah. Colleagues were quoted as saying that you had become increasingly paranoid. Would you say you were paranoid? Sure. First of all, what is a black man without his paranoia intact? [LAUGHTER] [APPLAUSE] If you get-- you might win $100 in a poker game and be on the subway, you gonna look over your shoulder. [LAUGHTER] They just said in everything I had $50 million. That's like making me a marked man. So did you go to a psychiatric hospital? In South Africa? OPRAH WINFREY: Yeah. Who-- [LAUGHTER] Huh? Oh, yeah, that's right. I was so-- I'm only asking because I needed to ask. No, I'm just-- I got to get people thinking. All right, who goes from America to Africa for medical attention? [LAUGHTER] [APPLAUSE] So true. I cannot imagine-- OPRAH WINFREY: Yeah, yeah. This is sounding like the most irresponsible journalism in the world. I cannot imagine being a journalist and hearing this from these people, and just running with it. It was on everything-- - Yeah. DAVE CHAPPELLE: --as a fact. OPRAH WINFREY: Yeah.

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