‘Chappelle’s Show’ Co-Creator’s Fave Skits

Ten years after it debuted, Neal Brennan dishes on what made his list of the show's top 11 moments.

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    Dave Chappelle (Chad Buchanan/Getty Images); Neal Brennan (Ethan Miller/Getty Images)

    It’s hard to believe that it’s been 10 years since Chappelle’s Show debuted on Comedy Central. Starring comic Dave Chappelle, the sketch-comedy series featured hilarious, irreverent takes on race (Clayton Bigsby, the black white supremacist), history (world’s greatest wars) and celebrity (R. Kelly‘s sex scandal), among other topics. It created oft-repeated catchphrases (“I’m Rick James, b–ch”) and furthered the cult-hero status of Eddie Murphy’s brother Charlie, funny man Donnell Rawlings (aka “Ashy Larry“) and crunk music pioneer Lil Jon (“Yeaaah!”). Not to mention that the musical guests on the show were some of the coolest ever (i.e., Yasiin Bey’s (then Mos Def) nimble “Close Edge” in a cab, Wu-Tang’s GZA performing “Knock Knock”).

    After its first two full seasons, Chappelle went from being an underappreciated stand-up comic and actor to a Richard Pryor-level comedy genius poised to cash in on a $50 million deal for the show’s third season. Perhaps the fame was too sudden, the expectations too high or the racial jokes too tricky for Chappelle, who controversially turned down the money, taking time off in Durban, South Africa.

    The Root caught up with Chappelle’s Show co-creator Neal Brennan to discuss what went on behind some of the show’s greatest sketches and characters. In the decade that has passed since the show debuted, Brennan has been spending his days doing stand-up and writing and directing other projects. He explained that he and Chappelle still talk often, but he admits that their friendship will remain at a certain level after going through some tough times during the final days of the show. “No,” Brennan flatly told The Root when asked if the two will work together again, before adding: “We’re friends, we’re kindred spirits.”

    “Dave was basically Chuck D and Flavor Flav in one person,” Brennan said when asked about the appeal of Chappelle. “He’s a revolutionary and also broad as f–k.”

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    Dave Chappelle as Clayton Bigsby (Screen grab courtesy of ComedyCentral.com)

    Frontline: Clayton Bigsby

    The character Clayton Bigsby, the blind white supremacist who just so happened to be African American, appeared in the pilot episode and set the tone for the show’s controversial humor and its liberal use of the n-word. Aside from that, the skit’s premise was just plain brilliant. “Dave had done 10 sitcom pilots prior to the show, and none were picked up because they were soft and watered-down,” Brennan said about the first episode and the sketch that set it off. “This was like “f–k it, if we’re going out, we’re going out guns blazing!”

    Interestingly enough, Brennan revealed that HBO turned down the show. “We pitched the show to HBO, and they looked at us like we had had leprosy.” We’re sure HBO is still kicking themselves over this missed opportunity.

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    Dave Chappelle as Rick James and Prince (Screen grab courtesy of ComedyCentral.com)

    Charlie Murphy's True Hollywood Stories

    Thanks to Murphy’s too-good-to-be-true tales about Rick James and Prince turning into full-blown sketches, Chappelle’s Show became a bigger phenomenon, as “I’m Rick James, b–ch!” became the catchphrase viewers of various ages, races and creeds would summon in just about any situation. While these stories were new to us, Murphy’s friends had always been privy to his antics. “Chris Rock told me that Charlie has told those stories for years,” Brennan revealed. “We just happened to be the only ones that thought maybe we should film these.”

    Brennan also recalled the moment when he realized the sketch would take the show to new heights. “I remember thinking that we might be in good shape because Dave’s wife was in a restaurant before the sketch had aired, and people who were just at the taping were saying, ‘I’m Rick James, b–ch’ at the table next to her,” he reflected. “After the sketch aired, someone in Vegas told me people at the blackjack table were shouting, ‘I’m Rick James, b–ch!’ Our show increased 100,000 viewers a week for the next 10 weeks after that sketch aired.”

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    Wayne Brady as himself (Screen grab courtesy of ComedyCentral.com)

    The Wayne Brady Show

    This sketch, in which Chappelle quit his show (foreshadowing perhaps?) and was replaced by Wayne Brady, turned the squeaky-clean image of the Whose Line Is It Anyway? improv actor upside-down. “We were doing a Larry Sanders type of write for the skit where we were revealing what people were really like behind the scenes, and it slowly became Training Day as we were writing it,” Brennan said. Interestingly enough, Brady hadn’t read the script until the day he arrived on the set. “He was reading it on the set, and I was wondering, what if he doesn’t like it? Credit to Wayne because he trusted me and Dave to do right by him.”

    It did take some coercing to get Brady to deliver one particular line. “I think he balked on ‘Does Wayne Brady have to choke a b–ch?’ and I had to coerce him, like, ‘Let’s just try it a couple of times,’ ” Brennan said. “It changed his life in a weird way. Not his whole life, but cool people like Martin Lawrence began to call him just to tell him he’s really funny. People saw him in a totally different light.”

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    Screen grab courtesy of ComedyCentral.com

    Jury Duty

    A vast majority of the sketches Brennan and Chappelle came up with were “for survival,” as Brennan put it. Constantly under the gun, many of the show’s greatest sketches literally came up at the last minute. The “Jury Duty” sketch featured Chappelle being interviewed as a potential juror on the Michael Jackson, R. Kelly, O.J. Simpson and Robert Blake cases.

    “The reason I love the Jury Duty selection skit so much is because we were in St. Thomas and we needed a sketch. We had both read the Michael Jackson article in Vanity Fair that was really impugning him back in ’04, and we started arguing about it,” Brennan explained. “We had good ideas at the right time. You don’t know that it’s the right time or the right idea; it just becomes very popular. It wasn’t like that. It was more like, ‘We’re in trouble and we have read-throughs tomorrow, do you have any ideas?’ “

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    Dave Chappelle as Samuel L. Jackson (Screen grab courtesy of ComedyCentral.com)

    Samuel Jackson Beer

    Before this sketch opened up season two, nobody had really paid attention to just how much Samuel Jackson screamed … except Brennan. Thanks to Samuel Jackson Beer, today you can’t help but notice it. “I think I was the first person to notice that Sam Jackson screamed in every single trailer,” Brennan said, while noting that Chappelle often joked around ordering Samuel Jackson beer instead of Samuel Adams. “I thought it was a really funny joke, and we needed a commercial for it.”

    What most people don’t know is that Chappelle wasn’t originally supposed to be Samuel Jackson. “We cast people, they’d do it and we knew that wasn’t how it needed to be done,” Brennan said. “Dave knew how he wanted it so he just would do it. Instead of counting on someone else to capture our imagination, we just did it ourselves.”

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    Robot Dancing Guy (Screen grab courtesy of ComedyCentral.com)

    Karl Lake's "Robot Dancing Man"

    That silly man who danced the robot in the most random places was almost completely by accident. “We were doing the ‘And 1’ sketch, and we thought it would be funny if people were just bugging out,” Brennan explained. “To heighten the bug out, [set designer] Karl Lake just started doing the robot.”

    Brennan can’t help but laugh at the mere thought of how bizarre the robot was and how much people caught on to it. “It’s so dumb that we kept doing it, and it just became a thing,” Brennan said in between laughs. “Exactly how you felt about is exactly what it was. It was for no other reason than ‘F–k it, we have a TV show, let’s get Karl to do the robot.’ “

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    Dave Chappelle as Lil Jon; Lil Jon (Screen grab courtesy of ComedyCentral.com)

    A Moment in the Life of Lil Jon

    Chappelle’s Show had a way of turning already popular people into iconic figures. Lil Jon was a star in his own right, but the idea to do a sketch on Lil Jon’s vocal tics (“O-K!” and “What?”) being part of his everyday persona, and then actually getting Lil Jon in on the action, was pure genius. “Lil Jon came on the show to be a musical guest, and the sound was bad so we couldn’t use it,” Brennan revealed about the origins of the sketch. “So we hung out with him and found out that Lil Jon is a smart guy. We started doing the ‘What?’ thing around the office. We’d start a conversation in a deep British accent and break into the ‘What?’ and ‘O-K!’ thing. Then it became its own sketch.”

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    Dave Chappelle as Tiger Woods (Screen grab courtesy of ComedyCentral.com)

    Racial Draft

    Part of the appeal of Chappelle’s Show was the unapologetic approach it took with differences in culture. What was thought to be taboo if said aloud in certain company was often celebrated unabashedly in sketches. The 2004 Racial Draft was one of those water-cooler moments coming to life in front of our very eyes. Hilariously, Tiger Woods is drafted by the African-American rep (Mos Def) from the community, the Jewish community selects Lenny Kravitz and the white community snags Colin Powell and Condoleezza Rice, and perhaps nothing is more surprising and humorous as the Asian community picking Wu-Tang Clan, with cameos from an overjoyed RZA and GZA.

    “We wrote in Wu Tang, but didn’t know if they would do it. We got RZA and GZA, and the night we shot we were on 34th Street across the street from Madison Square Garden,” Brennan said. “At one point, the RZA disappeared for an hour, and we couldn’t shoot. He came back and told us he was across the street at the Fade to Black retirement concert being filmed for Jay-Z’s upcoming movie.”

    RZA’s disappearing act just to check on Jay-Z’s supposed final show for a few moments gave some gravity to the situation. “So we were doing our thing here, and Jay-Z and The Roots are across the street doing theirs,” Brennan recalled. “That was special.”

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    Dave Chappelle as Tron Carter (Screen grab courtesy of ComedyCentral.com)

    Law & Order: Tron Carter

    Perhaps this episode can be appreciated more now considering the disdain most people have for CEOs who do white-collar crimes. A premise that flips the seemingly two different ways that the justice system handles crimes committed by rich citizens and those committed by the not-so-rich turned into a side splittingly funny sketch in which Tron Carter (Chappelle) pleads the “Fif.”

    “I believe that my sister was upset that Allen Iverson got to turn himself in at a predetermined time [for charges of three felonies and six misdemeanor charges in 2002], and the chairman of Tyco was perp-walked,” said Brennan. “A 60-year-old white guy got perp-walked and Iverson didn’t. I thought it might be a good sketch.”

    While the sketch was funny, it wasn’t until the final scene in which Tron exercises his right to the Fifth Amendment that it really took off. “Dave’s performance in that is unbelievable,” Brennan said, before revealing the real beauty of the sketch. “Basically, the whole Tron and the Fifth Amendment thing was totally improvised. It wasn’t written at all.”

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    Scene from "Mad Real World" skit (Screen grab courtesy of ComedyCentral.com)

    Mad Real World

    What would it have been like if MTV had featured an African-American majority and a single white cast member in the Real World house? Chappelle and Brennan did just that by taking Chad and sticking him in the house with a band of misfits including former inmate Tyree (Charlie Murphy) and completely belligerent Tron (Chappelle). Night vision, masturbation, stabbing and a comment about Katie’s breasts made the parody one that is still burned into some of our memories. Brennan addressed rumors that the sketch was almost entirely adlibbed. “Dave would ad-lib a lot,” Brennan said about Tron’s antics on that episode. “We’d write a lot, get on-set and realize we needed more. You can call it ad-libbing but it was just more writing.”

    And if you’re wondering about the Katie line: ” ‘Katie got some big-ass t–ties’ was totally improvised.”

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    Kanye West performing "The Food" on Chappelle's Show (Screen grab courtesy of mojvideo.com)

    Musical Guests

    Aside from the incredible sketches, many will remember Chappelle’s Show for its musical guests, such as Mos Def, Talib Kweli, Slum Village and an early Kanye West, who brought hip-hop to the forefront. Like Arsenio Hall’s talk show before it, Chappelle’s Show became the place that hip-hop simply had to reside.

    “I think that was literally Kanye’s first time performing on TV,” Brennan said of West’s performing of “The Food” with Common. “I don’t think anyone would believe me today, but Kanye was extremely shy on his first two takes. I told him to pick a camera and play to it. Now, you just go, ‘That couldn’t have happened.’ He had never been on TV before. He killed it on the third take, but just think, he was extremely shy then and look who he is today.”

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