High Times Greats: Dave Chappelle

The hit comic speaks out in a 2004 interview.
High Times Greats: Dave Chappelle
Dave Chappelle by Len Irish

Lenny Bruce did it, Richard Pryor did it, and Dave Chappelle does it: confronts hate with laughter. David Katz interviews the living legend in an interview from the March/April, 2004 edition of High Times, republished here on the occasion of Chappelle’s 47th birthday on August 24.


Dave Chappelle is one achingly funny dude.

Just ask viewers who have tuned into Chappelle’s Show, his Comedy Central hit, where they make the acquaintance of characters like Tyrone, “the goofiest crackhead in the town,” who is lured to an intervention by the prospect of, what else, free crack. (“Is this the five o’clock free crack giveaway?” he pants breathlessly, as he barges through the door.) He’s confronted by various former friends and victims, such as Rhonda, who “was very hurt that you carjacked me that time,” and Ginny and Rob, the liberal white couple who took him in so he could study for his real estate license (“You sold our house and kept the money. Four hundred and fifty thousand dollars!”), and his supervisor at the post office, who had to let Tyrone go when he snorted up an anthrax letter meant for Senator Tom Daschle. The cunning but irredeemable addict (“You all act like crack is so bad!”) fervently agrees to go into rehab, right after a visit to the men’s room (“But first step is first; I need to go to the bathroom!”), where he escapes by flushing himself, feet first, down the toilet bowl.

Or meet Clayton Bigsby, a blind Ku Klux Klansman, author of I Smell Nigger, Nigger Stain, Nigger Blood and Dump Truck; a driving force behind the Southern re-emergent white supremacy movement, and the subject of a parody “Frontline” documentary, complete with the palpably anguished white narrator. There’s only one minor problem: Clayton Bigsby is black, having been raised in an all-white orphanage for the blind, where, as the director states, “We figured we’d make it easy on Clayton by just telling him, and all the other blind kids, that he was white.” So when he “smells nigger” at a truck stop where the only black person in sight is himself, you know something is definitely askew.

And please don’t bother telling legally-challenged R&B singer R. Kelly what a pisser Dave is, unless perhaps you want a punch in the mouth. The raunchy Romeo was accused of shooting homemade hidden camera videotapes that show him having sex with a 14-year-old girl and then urinating on her face. He was mercilessly skewered by Chappelle in his now infamous faux R. Kelly music video, “Piss on You,” in which Dave, as Kelly, sprays dancing homegirls with a garden hose from a yellow barrel labeled “Kelly’s Urine” as he croons lines like, “Gonna pee on you. Drip, drip, drip,” and “Your body, your body…is my Porta Potty,” and “Only thing that make my life complete is when I turn your face into a toilet seat,” all in Kelly’s soulful falsetto style.

Also on the underage sex tip is a dead-on expose of the sexual molestation of young Jedi Knights by their masters, complete with a press conference from Skywalker Ranch featuring Yoda’s denial, in perfect Yodaspeak: “No have sex with boys, Yoda did not. Tired Yoda is. Resign he will.” However, reporter Chuck Taylor (Chappelle, whitened-up in a blond wig) rolls a hidden camera videotape of Yoda and apprentice Qui-Gon Jinn quaffing coke and getting stupid. “Get down do you? Good blow this is! Horny it makes me,” says Yoda, stuffing The Force up his itty-bitty nose.

A natural mimic whose droll stand-up delivery is blessed with pitch-perfect vernacular and precision timing, the 31-year-old Chappelle’s sidesplitting sketches also serve as caustic critiques of America’s cultural and political contradictions, sparing neither racial nor sexual sensitivities. Not down with pallid, politically-correct bullshit, Chappelle’s audacious, ironic satire implodes stereotypes and unhinges the squeamish with its irreverent, obscenity-laced hip-hop argot and gross-out, no-holds-barred potty humor.

Laughs are job one to Chappelle, a comic wunderkind who began telling jokes on the street and later progressed to performing in local comedy clubs at the age of 14, chaperoned by his mother, a Unitarian minister who bet the dank, smoky, boozy, sexually-charged atmosphere of a comedy dive was a better backdrop for her son than the crack-crazed, crime-driven, gun-crammed Washington, DC, streets of Ronald Reagan’s 1980s’ “Morning In America.” Wanted for scene-stealing in films like Robin Hood: Men In Tights (1993) and The Nutty Professor (1996), in which he played opposite one of his personal idols, Eddie Murphy, Chappelle made the most of his roles. With comedy partner Neal Brennan, Chappelle cowrote Half Baked, a 1998 homage to Cheech and Chong, in which Chappelle portrayed good natured, chronic-crazed janitor Thurgood Jenkins. The film is now considered an herbal classic, the DVD a must-own for college students matriculating in marijuana.

But it was his 2000 HBO comedy special, Killin’ Them Softly, with its outrageous bit about a baby in diapers selling weed on a ghetto street comer, and a deconstruction of Sesame Street (that labeled The Count a pimp and deplored the hideous persecution of Oscar the Grouch by the other Muppets), that put Chappelle on the stand-up map. This led to appearances on Def Comedy Jam, and eventually his own show on Comedy Central, where laughs are real. “I show those sketches to a live audience,” says Chappelle. “We don’t use a laugh track. The laughs we get on TV are the real laughs from the audience.”

Many of Chappelle’s sketches are what-ifs: What if Wu Tang Clan ran a financial services company dispensing investment advice to white suburban families? (“Smith Barney is a bunch of bitches, old-time farts. Yo, you need to diversify your bonds. This ain’t Trading Places, nigger, this is real fucking life.”) Or this one: What if MTV’s The Real World surrounded one clueless white guy with five “of the craziest black people we could find?” instead of the other way around? Hapless whitey Chad is introduced to his roommate: menacing, spliff-puffing, doo-ragged ex-con Tyree, who gives him a mean look and tells him: “Lookee here, Chad, for the entire period you in my room, I better not catch you standing up peeing, You sit down when you pee, you understand? That’s right. Now get your fat ass out of here, white boy.” Poor Chad.

And what if, as in an upcoming show, there was a blissful, wholesome, white Ozzie and Harriet-style 1950s American family who just happened to be named The Niggars? (“Hi, Niggars!” happily shouts Chappelle, the milkman, in an all-white uniform, a giant grin on his shiny black face, as he drops in on the family to make his delivery.)

Chappelle traces his comic lineage from Lenny Bruce through Richard Pryor and Eddie Murphy, with Bill Murray, Cheech and Chong and old Bugs Bunny cartoons in the mix. Richard Pryor was an especially important influence. “I liked him when I was a kid, but I didn’t understand the depth of what he was doing until I was an adult.” Has comedy changed since Pryor, and even Murphy? “Crowds don’t listen like that anymore. This is the MTV generation; they got a shorter attention span. I try to do it my way; I think I got a slower cadence, more deliberate than a lot of my contemporaries. They say you gotta train people to listen to you.”

High Times sat down with Chappelle in New York City during the week the new season of his Comedy Central Chappelle’s Show was being taped.

High Times: Let’s begin with Tyrone the Crackhead, perhaps the Ultimate Crackhead. Did any black people give you shit, saying this was not the most complimentary picture of the black experience, even though it’s funny as hell?

Dave Chappelle: Naw. As a matter of fact. I got a letter from a teacher who sent a letter that a student wrote about me, just saying how great that was and how it persuaded him to never do drugs, which made me laugh. But I said, That’s kind of deep, you know? Tyrone. Man, you know I grew up in DC in the eighties, man, during that crack epidemic; I seen this guy. I’ve never seen somebody desire something like they did crack in the eighties.

Like the itchy, impatient, cock-sucking Crack President in Killin’ Them Softly?

Yeah. Crack, man, it was so overwhelming, and it’s tragic, and I guess those are the things that lend themselves to elements of comedy. Originally, Tyrone was a piece I did in my act. First sketch he did was the one where he went to the school and spoke to the kids during the Drug Awareness Week. And something like that actually happened to me when I was in school, during the Nancy Reagan years, and they sent this guy who was a recovering addict to talk to us about the ills of drugs, but the way he was saying this shit? Made drugs sound fun? Like I can’t even describe. He’s talking about doing acid, and him and his friends were laughing, and then he said ‘I talked to a guy for two hours and then I realized he wasn’t there, like I’d hallucinated it.’ I guess that was meant to scare us, but all the guys were like, ‘Damn, look it, we gotta get some acid!’

Like Scared Straight. To some kids it made prison look bitchin’.

Exactly. It backfired. And I mean, that’s one of those things that stays with you, and Tyrone actually grew out of that.

Did you have many eye-opening racial incidents when you were younger? Not something dire or drastic, but something like your “chicken” bit, where the white guy at the fast food place in Mississippi just assumes you want the chicken special?

Oh yeah, I had a bunch of those. But I think overall, more than any one incident, was just what I saw around me. A lot of shit is unfair, man. Like I wasn’t always a famous comedian. When you’re nobody, and you look around at what the world is, and you’re black, man, it just seems real daunting. Like how could I ever matter in a world like this? You know what I mean? Like, how many troops have died in Iraq as of today?

Almost five hundred, I think.

Close to five hundred? When I was in high school in my freshman year, maybe over five hundred kids—kids—got murdered in the Washington, DC, area. They’re all black! No national outcry, no nothing. This wasn’t Baghdad; this was the nation’s capital, man! I mean, there are so many inequities like that. You know crack wasn’t a problem until suburban kids started smoking crack.

Do you have any political thoughts on crack?

I know the conspiracy theory. You know, it wouldn’t surprise me if it ever came out one day that crack was placed in the community like a scourge put on it. But even still, even if the powers-that-be did that, I mean, even the country at large, it just seemed like they didn’t care. It’s just something that happens to “them.” I can always see things big enough to not take that personal, which is why I think I can talk about it. I’m not gonna say I never take it personal, but for the most part I think I can see the bigger picture.

You know, I’ve hung out with people that I consider racist; I’ve smoked weed with racists of all different colors. I know it’s not personal, I think it’s just the broad strokes of the world. It’s so ingrained in our culture; it’s got such deep roots in American life. And the thing is that it’s always kind of under-recognized; we don’t like to deal with these things in our past. But if America was a dude, the best tiring to do would be to confront your problems and admit that you have these problems, and then that’s how you get past them.

Should America go into psychoanalysis?

I say it’s about time! If America was a single dude, he’d be overworked, he’d be a drug addict, he’d have a pussy problem, he wouldn’t be able to keep his dick in his pants, he’d be burnt out, and he’d be about ready for a nervous breakdown. He’d be paranoid as shit. If America was a dude, that’s pretty much what his character would be like.

The chronic. It figures in your work?

Yeah. Half Baked and all that.

Did herb hit you hard when you first did it, as in the movie?

When I first smoked weed I didn’t like it so much. First time I smoked I was twelve. It didn’t really do anything for me. You hear stories, “I was paranoid, I was this, I was that.” Nothing. Then I smoked pot once in high school. I think the first decent experience I had with weed was when I was nineteen. I started smoking again, and that’s when it was like, “Hey, this is not bad.” By that time the chronic had come out, and I loved it. Half Baked, man, I wrote that movie, my buddy and me did. I was livin’ that lifestyle, I wasn’t just imitating that lifestyle.

Did you have any qualms about making a drug movie?

Oh, was I nervous about it? Not at all. Not at all. I didn’t see anything wrong with smoking pot, you know. I mean, now I’m older, I can see where it can be less than beneficial. I still don’t necessarily feel like it’s criminal. Should Tommy Chong be in jail right now? Naw! I still can’t believe it! I’m surprised you don’t see more Free Chong shirts. You know, this is like crazy! Like I said, I can see where it’s less than beneficial for the corporate schedule. But nine months in Federal prison? For selling bongs?

If pot were legal, would that do good things for race relations?

I think potentially it could. I mean, socially, when I think about the people I have smoked pot with, they are such an eclectic mix of people that I probably never would have spoken to a lot of them if it weren’t for pot. Alcohol doesn’t bring people together like that. You put these same people together, they’re drinking alcohol, they end up fighting. So I mean, do I think it’s the cure-all for America’s problems? No. Do I think this shit is a good way to relax after a stressful day? Sure! In a live-and-let-live society I don’t know if it should be considered criminal. It’s not like people are breaking into cars to get pot money. If Tyrone smoked as much weed as he did crack, he’d fall asleep long before he committed a crime. [Laughs]

You do white people very well.

Thank you.

There’s Chip, your drunken white buddy, and Johnson the Cop. And Ralph Henderson, the Pop Copy training manager who’s black but talks white. Where did you learn their odd inflections and bizarre pronunciations? Is it a matter of listening?

I grew up in DC. In elementary school I lived in Silver Springs, Maryland, which is a pretty mixed area, black and white. Then in middle school, I lived in Ohio. Near Dayton. It’s very white. And then in high school I was in DC; it was very black. But I guess I grew up in so many different places, and met so many different kinds of people, well, that white cadence was something I picked up.

And then I watched television a lot. I used to watch Miami Vice, and Sanford and Son—that was always a big one in the house, a lot of Saturday Night Live, Arsenio Hall. I used to watch an incredible amount of TV growing up, incredible; way more than is healthy. Bugs Bunny cartoons—I watched all of them, for hours. I like the older ones.

Dave, what have you got against the Ku Klux Klan? [Laughs]
[Laughs, Gives me funny look] Damn!

Only kidding.

Well, I guess they embody a particular brand of hatred that’s very misguided, and the fact that they organize behind something like that is very unfortunate. But they’re very intertwined in our history, after Reconstruction, and the Civil War, where these hate groups emerged. It’s not that I have anything against them, as much as the ideology or the philosophy that makes people join an ill-informed, misguided philosophy.

That brings us to Clayton Bigsby. Were the people at Comedy Central squeamish about the nigger word being thrown around so much?

Actually they were surprisingly receptive to it. Not gonna say they weren’t nervous. I think the first fight about it was I wanted to put it on the first episode, and I think that’s when they were like “Whoa!” That and the fact that they thought that the sketch was too long. They wanted me to cut certain parts of it out, which I absolutely didn’t want to do.

Did you feel it was shocking when you did it?

If I did it at a nightclub? It wouldn’t be shocking at all. But somehow in the context of television, suddenly it takes on this whole ’nother, like, “This is crazy, this is shocking.” I think if I polled my family of people that actually watched this show to see me, I don’t think they’re shocked. I think they laughed, they enjoyed it. But I don’t think that I ever shock. It’s hard to shock people nowadays.

How many of your characters are based on people, or things you’ve seen?

Tyrone, I’ve seen. Bigsby was from a story my grandfather told me. My grandfather actually may be white, I don’t know. He was born in a white hospital in 1911. He’s at least half black.

His mother couldn’t have been black, right?

There’s no way. There is no way a black woman under any circumstances could have a baby in a white hospital then. But he looks like a white dude, and he was blind from birth. But as far as he knows, you know, he grew up in DC. Black dude. As far as he’s concerned, he’s a black guy. And he was on the bus the day after Martin Luther King got shot, and all the brothers were like, “What you doing on the bus, you cracker, you honky?” And all this, and my grandfather was saying like, “What is a white person doing on the bus? Is he crazy?” He had no idea they were talking about him. So he told us that story, and I just did the inverse of that for Bigsby.

If white people didn’t exist, would black people still be funny?

[Laughs] That’s hard! That’s a big If! Wow, if white people didn’t exist, that’s a huge If! I can’t imagine a world without white people! I’m gonna go out on a limb and say yes. Yes, ’cause I’m sure there were funny black dudes in Africa, before they met white people. They might not be as funny.

If white people didn’t exist, would black comedians need to invent them?

If white people didn’t exist, who would we beat in the Olympics?

[Laughs] What do you make of the ‘wigger’ phenomena? Aka white niggers? As in the Bigsby sketch, when four white guys in knit caps and hoodies, blasting hip-hop in their convertible, pull up next to Clayton’s pick-up truck, and he starts going berserk, and they high-five each other for being called nigger?

Man, it’s crazy! I like it, actually; all in all, I’d say I like it. The sad part about it is that they’ll enjoy black culture as they grow up, but at a certain point, as soon as it’s time to get a job or move on in their life, they’ll throw this culture aside like they had never participated in it, and maybe even look down on it later in their life, and look down on the people who are in it. And that’s unfortunate, but as a young person I gotta say I enjoy seeing black culture in the mainstream right now.

It’s kind of a compliment.

More than kind of. I think it’s good for race relations that so many white kids’ heroes are black dudes.

Did you ever think you’d see that?

There are black people throughout popular culture who whites and blacks have been unanimous on. I mean guys like Eddie Murphy, whereas that could have been the kiss of death years ago if you’re a black entertainer, because once that white audience embraces you, a black audience might lose respect for you.

And guys like Eddie Murphy didn’t pander; they stayed black.

Yeah. They stuck to their guns, man. A Richard Pryor, or any of these guys. So I think it’s a beautiful thing, man. It brings a lot of people together. Like I said, I don’t know how binding it is. After a certain point, they just might give up on us!

Just to go back to wiggers, do you think white people are ever qualified to use the word nigger?

It’s funny, I was having a conversation with Mos Def, who’s a rapper, actor, comedian, and he said that it was an excluding word, originally. To call you a nigger is kind of like, “Get out of here; we don’t want you.” Now instead it’s cool to be black, and we call it “Yo’ one nigger;” and now it’s still exclusive, but it’s the other way, and we can say this, but you can’t say that. And in a very personal situation, maybe I’ll let it slide, but in general I don’t want to hear white people say that. It’s because, again, it could be a fad they’re going through.

But in a way, I like the fact they’re calling you that, and it’s a positive connotation, because nigger is a word they use for black people that weren’t down with their program of slavery. If a slave gave them a hard time they called him a “nigger.” And that’s the kind of slave you wanna be. You don’t want to be the agreeable, smiling motherfucker; you want to be that disagreeable, ornery—if you would—get-out-of-my-sight motherfucker. All these things are contextual, man. You can say most anything so long as you’re not malicious about it. But you know, your intentions make or break everything, man.

Are there times you hear people say it, and you go “How’s this guy saying it?”

Yeah. If you have to ask, they probably didn’t do it right. You know what I mean? You know, there are some people who can just get away with it. Lenny Bruce got away with it in the sixties. Pryor got away with it, I get away with it, you know, and it’s just ’cause it’s no malice, man.

What do you think of Lenny Bruce?

Imagine, that was the first time anyone ever talked like that, in public, and as a comedian, up until that point. And Richard Pryor more so. I think that Richard completely stretched that out.

Cursing?

Not just the cursing, but the shit they used to talk about! Lenny Bruce was talking about the Kennedy Assassination like it was funny, after it happened! Richard Pryor talks about the cops beating up Negroes, and “Can we break a nigger? It’s in the rulebook: Oh, it says right here we can break a nigger.” I mean, the substance of the shit they were saying, that’s what I was impressed with. And not just that it was only daring; it was daring, but the shit was really funny, man, above anything—it was just funny.

Is that the most important thing? Beyond social implications?

I mean look, whether you pull shit out of a box like Carrot Top, or juggle, or talk about politics, I still feel like the crowd just wants to be entertained. For instance, I’m doing a special in June. I’m not gonna go and deliberately write war jokes, unless there’s something, an angle I see, like, Oh, this is really funny. And it’s a good point. Like Piss on You? Hey, like, I almost didn’t do it, just because I felt bad for R. Kelly. Yeah, like before we shot it. But after we recorded the song, I felt weird, like, man, I don’t know if I should do this, I got all the guy’s records, it’s a terrible time in his life. Am I kicking a man when he’s down? Was it wrong to kick a guy when he’s down?

But when I thought about it, I literally was like, this shit is too funny, if I don’t do it, I’ll be mad at myself. ’Cause it’s too funny. And the other thing was, I didn’t think it was the worst. I figure, that’s the least of his problems. It might actually help him to give people an opportunity just to laugh it off.

Get it into perspective.

Yeah, exactly. You know, that’s terrible, to pee on that damn girl.

Do you think this R. Kelly, Michael Jackson, Kobe Bryant shit, this media focus on “famous negroes gone wrong,” is all distraction? Like, let’s get some black guy fucked up so the public doesn’t fixate on the fact that everything else is going to shit?

That’s funny, because the last time we heard from Michael Jackson in such a big media frenzy was right at the beginning of the invasion of Iraq. And right when it was happening, that’s where that special came out with the boy that made the allegations. And I just remember thinking: “We’re on the brink of a war, and Michael Jackson is the lead story on three networks?” Like he was on two networks at the same time, two of the big four. I think he’s America’s scapegoat, Michael Jackson. He’s just somebody to hate when shit’s going wrong.

What are some of the drawbacks of being famous?

Obviously, less privacy. Scrutiny. Scrutiny is a form of oppression in a way, even if it’s unintentional, because a scrutinized person will never act natural. If you know somebody’s watching you eat, you’re gonna start thinking, “How am I chewing my food?” Things that you normally just do and are natural about. So like, in my personal life, I used to be one of the funniest dudes you’d ever want to hang out with, but now I just save it for the stage ’cause it’s safer. I feel too inhibited when I’m around strangers or something because I feel like, you know, you never know, one out of ten people are always out to get you. Two out of ten, five out of ten—as you go up the ranks it seems like there’s more malicious people. You gotta be so cautious. That’s no fun, man.

Is that a jealousy factor, you think?

I think it’s jealousy, I think it’s desperation. Look, man, like I said, sometimes the idea of mattering in this society is daunting. When you meet a person who’s famous, all kinds of different shit comes into people’s minds. Take a totally nice, benign person who begins hanging ’round a famous person; you might see a dark side they never had. You see the best in people—sometimes they’re very accommodating, maybe even too accommodating—and then you see the worst in people. Like maybe they figure, “If I can trip this guy I can get something.” You know, it’s par for the course, but it’s a lot of scrutiny, and it forces you to be more self-aware. And I’m not interested in that. I like just living my life, spouting my opinion like I really mean it, and then changing my mind the next day. You know what I mean? [Laughs] I change my mind all the time. I believe what I believe, until I see a better way.

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