The Rise and Fall of Chappelle’s Show

This is the definitive Chappelle’s Show oral history, bitches. Experience the unlikely triumph of a comic maverick and his crew. By Keith Murphy & Peter Rubin

Chappelle’s Show is the greatest sketch comedy of all time. There, we said it. We can already hear the proverbial groans of disagreement. What about the G.O.A.T. Saturday Night Live…you know Belushi, Murphy, Ferrell? Well, let’s see the legendary SNL become a cultural phenomenon in the age of cable TV and shrinking Nielsen ratings. But Dave can’t fuck with the Wayans family’s multicultural breakthrough In Living Color. Sure Dave owes a lot to Keenan. But In Living Color overstayed its welcome, while Chappelle’s Show left a pristine corpse, a la Jimi Hendrix and Tupac. Mad TV? You’re kidding, right? Really, who cares why Dave bailed out of his landmark show. He can go on Oprah and Inside the Actors’ Studio and explain his meltdown all he wants. His show shouldn’t be, and isn’t, defined by his abrupt exit or self-medicating trip to Africa. Its tombstone should read: Here Lies the Comedy With the Biggest Balls. Period.

Season One

Chappelle’s Show premiered on January 22, 2003

The Mad Real World

Christian Finnegan (“Chad”): I’m a standup comic, and so was Neal. One day, he was like, “You know, I’m doing this show with Dave, and we’re doing this bit that you might be really good for.” When you get cast for something like that, you have to sit down for a table read together, and read the script out loud. It was that sketch, the Clayton Bigsby sketch, and something else. Everybody was looking around the table like, “I can’t believe how funny this is.”

Charlie Murphy (comedian, actor): People liked the [tough] characters I did from CB4, Players Club and Spike Lee’s films, and when people would think of someone playing a gangster-type role, my name would come up at the top of the list. So when they were writing “The Mad Real World” sketch Dave was like, “Yo, we need Charlie Murphy to play this thug- ass character named Tyree.” That was my first sketch.

Finnegan: No one ever comes up to me quietly and says, “Hey, I really enjoyed your work in ‘The Mad Real World.’” People walk up to me in the middle of a dinner with my girlfriend like, “Katie’s got some big-ass tittays!”

Ask A Black Guy/ Negrodamus

Paul Mooney (comedian, writer, actor): I basically came up with “Negrodamus” and “Mooney On Movies,” while Dave came up with “Ask A Black Guy.” “Negrodamus” was actually supposed to be Niggerdamus, but we had to clean it up. You know when I say “nigger,” it’s like the devil is saying it [laughs].

Player Haters’ Ball

Bryan Tucker (writer, “Player Hater’s Ball”): Dave and Neal have a good idea, and they have a set-up, and then they do like 10 takes. Dave does a little something different every time. So a lot of the great lines you see aren’t necessarily stuff that you’d see written in a script.

Donnell Rawlings (comedian, actor; Ashy Larry): Ten minutes before we go shoot “Player Haters’ Ball,” my character didn’t have a name or anything. I went to hair and makeup, told them to give me a Jheri-curl wig. Then I went to props, and I asked for a Moët bottle with an activator on it so I can just squirt my hair down. They didn’t have that, so they gave me the aerosol can. I’m spraying it, people laughing and shit, three minutes before shooting. I didn’t have a name, dialogue or anything. Neal told me to make my name up. I walked past the mirror like twice, looked in it, and said, “Man, I feel beautiful!” That’s when “Beautiful” was born.

Bill Burr (announcer, “Racial Draft”): Dave and Neal were real cool with improv. They were like, “If it’s funny, it’s going in.”

Rawlings: Dave always does something to let everybody know why it’s Chappelle’s Show. When he got to the page flip, we had already had 18 hours in. It had to be like 2:30, 3 in the morning—we was all joked out! Dave was the only one who kept it moving. “She look like she wear underpants with dickholes in them!” That was the end of that. It’s a wrap. Let’s go home.

Season Two premiered January 21, 2004. Less than a month later, the Season One DVD was released and became the best-selling television DVD ever. The confluence of the two brought Chappelle’s Show more exposure than it had seen up to that point.

Tucker: It wasn’t until Season Two, with things like the Charlie Murphy stories and Wayne Brady stuff and “Racial Draft” that kind of got into people’s consciousness because they were really starting to do things that were different from your normal sketch stuff.

Rawlings: It was nothing for us to do a 17-hour day. We had so much fun doing it, nobody was worried about working overtime. We were part of some hot shit, you know?

Racial Draft

Burr: Everybody always comes up to me and talks about “Racial Draft.”

RZA (rapper, actor): I remember Dave sending the [“Racial Draft”] script through my BlackBerry. Before that, we had already done the “Wu-Tang Financial” skit. When we got to the set, we saw Mos Def dressed up in those crazy fucking clothes and wig. I just knew the shit was going to be stupid. When the Wu-Tang Clan got picked by the Asian delegation, that was just crazy.

Angie Martinez (New York radio personality): We had to stop several times during the shoot because it was too funny. The truth is, they kind of cut out [my part] because it was supposed to be longer. There was a segment where you actually saw Elian Gonzales and he was [in Cuba] like “I ain’t got no bling over here! I ain’t got no laptop!” [laughs] It was great, but I guess for time they had to cut it down.

RZA: I was in Austin, Texas, four months ago. I’m going into this club, and I got a few homies with me and one of my people was like, “RZA is paying to get into a club? Fuck that…do you know who this is in line?” The bouncer finally recognized my face and screamed, “Konichiwa, motherfucker!” [laughs] Everybody just fell out.

The Niggar Family

Questlove (the Roots’ drummer; Chappelle’s Show’s musical supervisor): The first music I wrote was for the “Niggar Family” skit. The strangest thing about it was Neal, Dave’s [white] writing partner. This was a skit within a skit. I was trying to teach the [Roots’ protégé act] Jazzy Fat Nastees how to sing the theme song and Neal was like, “No, it’s n-i-g-g-e-r…” he just kept saying the word nigger. And I’m like, “Yo, man! This motherfucker is crazy. Did I just hear what he said?!” It was rough for me in the beginning [laughs].

Charlie Murphy’s True Hollywood Stories

Murphy: The Rick James skit was all by accident. Dave and I were just at the lunch table talking about [some of my experiences] during a shoot for “Calvin’s Got a Job.” And all of a sudden homeboy just lit up and said, “We can do this as a sketch.” I’ve known Rick for years, so I got in touch with him and said, “Yo, this is what’s popping, man. It’s going to be funny. I’m going to fax you all the information.” And Rick liked it.

Questlove: Dave would show up at Okayplayer shows, the Roots’ shows and Talib Kweli shows. That is how Kweli was able to get Dave to do the Rick James intro for Reflection Eternal. That whole Rick James character first appeared on the Kweli record. Months later I was in a snow storm up in Boston in 2002 and I got a call from Brennan. He’s like, “Yo, where’s your fax machine? You have to read this script. We just concocted the funniest skit ever…it’s Rick James.”

Burr: I lived near the editing suite, and Neal called me like, “You gotta come up here. I don’t know if we can top ourselves on this one.” When I went up there and saw it, the first three minutes I was dying laughing, and after that, I was just kind of in awe. That was the one that blew the show up.

Murphy: I knew it was something [special] when we took it over to my baby brother [Eddie Murphy’s] house. I was like, “Check out this Rick James sketch.” And we watched it and he was silent throughout the whole sketch, so I thought it was horrible. Soon as it stopped playing, he just said one word: “Genius.” And then busted out laughing like, “Play that shit again!”

Rick James (singer): I love Dave. I think he’s brought something to comedy that people haven’t seen before. He’s a beautiful human being, and Charlie Murphy is a very dear friend. Everywhere I go, white folks, black folks, green folks, I hear “I’m Rick James, bitch!” I don’t really think David did it purposely. I take that back. He probably did.

Questlove: The Prince skit only came to be because Rick James had given it away [that Charlie had gotten beat by Prince in a game of basketball]. It was just a crazy premise for a sketch.

Murphy: It was real fucking hard to keep a straight face looking at Dave wearing that Prince outfit [Laughs]. He had motherfuckers screaming. Every time they said, “Cut” everybody just busted out laughing. Later on, the word came back that Prince said to Dave, “It wasn’t that I was a great basketball player, it was that Charlie was horrible.”

Questlove: We went to a secret show, back in 2004 after Prince got inducted into the Rock & Roll Hall of Fame. And Prince was onstage playing the dozens like, “Dave Chappelle…you Grover-looking, Bug-eyed Oscar-the-Grouch, Pancake-eating, no-basketball-playing!!!” He really liked the skit.

The Lil Jon Skit

Lil Jon (rapper/producer): My homeboy Cipha Soundz DJed on the show. One day he was like, “Man, you gotta see this sketch that Dave does on you!” I was like, “Get the fuck out of here! Dave Chappelle is doing a sketch on me?” I was watching the show in the studio. The shit came on, and we were just bugging out. Then, I was in an airport in Miami, and an older white woman came up to me and was like, “I love you!”

Burr: I was doing stand-up at this festival in Tennessee called Bonnaroo—a bunch of white hippie bands, alternative shit. I was backstage waiting for this band to come out, and all of a sudden the lights went out. Five thousand people waiting in the dark, and then you just hear some kid in the back go, ‘Whaaaat?’ Then somebody else yells, “Okaaaay! Yeeaaah!” It sent a chill up my spine.

Lil Jon: Imagine people screaming that at you for three years. The same shit.

Wayne Brady Takes Over

Mooney: The whole Wayne Brady sketch came out of Negrodamus when I said, “White people love Wayne Brady, because Wayne Brady makes Bryant Gumble look like Malcolm X.”

Wayne Brady (comic/actor): [I] wouldn’t miss an episode of the show. One day I’m watching Paul Mooney do “Negrodamus.” [I’m] sitting with my wife, saying, “Paul is so funny, you gotta watch this.” And then the whole Wayne Brady thing came up. Dave was one of those cats I respected so much and thought was funny. It’s like someone you like, and you see them walking across the street and you’re like, “Hey, good to see you” and they’re like, Smack!

Neal Brennan: (co-creator of Chappelle’s Show): About a month after “Negrodamus” aired, we were at the NAACP Image Awards, and Wayne Brady bumped into a crew from the show. He bought them drinks and eventually let them know how upset he was about the sketch. Apparently, he [saw] the show, and the joke came on. Dave found out he was upset and called him the next day.

Rawlings: When I met Wayne Brady, he came up to me like, [imitating Wayne’s voice] “I just wanna say, I think you guys do amazing work on the show. It’s funny, phenomenal work. History in the making.” Blah, blah, blah. I’m looking at him with his voice, like, “This nigga really talk like Wayne Brady!” I said, “Nah man, you the nigga!” He looked at me like, “Nobody has ever called me that type of nigger before.” [Laughs]

Mooney: [The Wayne Brady skit] added a new dynamic to his career and it was just funny. I respect Wayne for doing the show, and for standing up for himself.

Brady: I curse. I’m not squeaky clean. [But] I didn’t like the term, “Slap a ho.” I’ve got a daughter; there’s something about [that] that’s too real. So we came up with the whole line “Is Wayne Brady gonna have to choke a bitch?”

Rawlings: Nobody could predict Wayne would use the “choke a bitch” line. He wanted to be like, “Yo, if Wayne Brady had to fight someone…” He was nervous about it. We all thought it was going to work, but you can’t force anybody or put their reputation on the line. But it turned out real funny.

Kneehigh Park Skit

Questlove: Dave had written the [Kneehigh] Muppet skit with Bobby Brown in mind. We made arrangements for Bobby to come to New York to record the songs with Charlie Murphy and Dave as muppets with STDs. But he got arrested on the way. We were stuck. We called André 3000 to see if he could do it, but Dre was working on Idlewild. So then we called Pharrell, who was in Europe. He would have canceled his European tour, if his manager didn’t smack some sense into him. [Laughs] We were shooting it seven hours before it was supposed to air. But at the last minute we were able to get Q-Tip, who changed “Vivrant Thing” into “VD Thing.” And we were also able to get Snoop Dogg to be one of the characters because he was going to do the “Weed Olympics” sketch, which got cut. That’s how a lot of things worked out for us.

Months after Season 2 ended, contract negotiations for the show dragged on. Meanwhile, the show had become a full-blown cultural phenomenon, thanks in part to the record-shattering DVD sales of Season One. The two-disc set would go on to sell well over 1.9 million copies, bumping The Simpsons’ The Complete First Season out of the all-time number-one slot.

Mooney: Chappelle’s Show outsold every DVD in the history of TV. And the white folks didn’t like it. I remember being at a big comedy session and one of [the Comedy Central execs] said, “Yeah, but [Jerry] Seinfeld is coming out and he’s going to outdo Chappelle.” But Seinfeld didn’t even come close; 8-year-olds don’t know Seinfeld, they don’t give a damn. They knew who Dave was.

Lil Jon: We were in Miami for the MTV Video Music Awards, in 2004. I’m driving down the street, and somebody is outside screaming, “Yeeaah!” I look over, and it’s Dave’s ass. So I jumped out of the car. Just imagine—the average person don’t see Dave Chappelle and Lil Jon walking down the street. That’s when I think Dave really saw how much people say the shit to me. People were just bugging the fuck out. The next day, on the awards, Dave said, “Jon, I’m sorry I did it to you.”

Murphy: I was doing an interview in a restaurant [in 2004]. My table was near the window and school was letting out. These kids were maybe 8, 10 years old. They stopped in front of the window and started screaming out, “Charlie M-u-r-p-h-y! I’m Rick James bitch!!!” That was deep.

Rawlings: In America, there is no street I can walk down without getting hit with “Ashy Larry!” Going into bars and having white boys tell me they love me, and want to do shots with me, and shit.

Lil Jon: I think they’re going to be saying that shit at my funeral. “He was a good man and, Whaaat?” Then the crowd will say, “Amen. Okaaaay!”

In December, 2004, after the much-publicized $50 million deal, production for Season Three came to a halt, then started up again in January 2005. In April, though, Chappelle abruptly disappeared—to Africa, it turned out. Though he returned soon after, the show never resumed.

Tucker: There’s a sketch that I hope they’ll show on the third season, called “Black Monsters.” I remember like two or three instances where the extras started laughing, and they had to do it again.

Rawlings: Charlie as Black Frankenstein, Dave as Black Werewolf, and Donnell as Black Mummy. When Dave disappeared, people asked, “Where’s Dave?” I’m always telling them he was a werewolf [laughs]. My last image of Dave was him looking like James Brown in the wolf man costume. That was the last we saw him.

Murphy: Hell yeah I was shocked. It’s like you go to work on Thursday and you wake up on Friday and the phone rings and they say, “Yeah, there’s not going to be any work today.” I wasn’t emotional about it. We were getting paid [union] minimum [wage]. None of us made money except for Dave and Neal. But we were happy to show up, because it was groundbreaking national TV and funny as hell.

Burr: I knew nobody was talking when people finally started asking me what I knew. All of a sudden I started getting the e-mails: “Hey man, this is just between you and me, dude. This isn’t going to get out anywhere…is Dave on crack?”

Tucker: I talked to Dave once about everything. There were too many people around to get into anything substantial. I’m just grateful to have been a part of it.

RZA: He’s funnier than 90 percent of the cats doing comedy. We looked forward to Chappelle like the next season of Cosby.

Mooney: Dave’s a lot like Richard [Pryor]. He’s an artist first, everything else is second. They offered him $50 million, but the money didn’t mean anything. Dave knew money was an illusion. You can’t take it with you. You’ve never seen a Brink’s truck following a hearse, and you never will.

Burr: I ran into Dave last fall at the Comedy Store in L.A. Everybody from Herbie Hancock to Gabrielle Union showed. Dave came out and did a killer set making fun of the whole “Dave is crazy” shit. He wasn’t on drugs or anything.

Finnegan: When the book gets written 20 years from now about TV, Chappelle’s Show is going to be there. It’s one of the shows people will always talk about.

Lil Jon: That show changed pop culture.

Rawlings: Whenever you think, “It can’t get funnier,” he took it to the next level.

Mooney: I’ve written for Richard Pryor, Flip Wilson, Red Foxx, Bill Cosby and Whoopie Goldberg. Dave is among those names. He’s a very intelligent comedian who happens to be a pothead.

Murphy: If it wasn’t for Dave, the world would still be calling me Eddie Murphy’s brother. He gave Donnell Rawlings, Bill Burr and myself the chance to go on the road. I saw Dave at the Comedy Store in L.A. and I just told him, “Nigga, you know you changed my life, right?” And he said, “You changed my life, too.” Then we hugged.

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